a) Interpretation: The structure of an given molecular formula C 8 H 16 to be predicted using 13 CNMR spectra. Concept introduction: The 13 CNMR spectrum gives information on the different electronic environments of carbon. As like 1 HNMR, the number of signals generated in 13 CNMR are predicted by performing symmetry operations (rotation or reflection symmetry). Only chemical shift values are reported in the spectrum but not the multiplicity and integration values because the coupling between two neighboring 13 C - 13 C nuclei are weakly involved due to the low abundance of 13 C isotopes of carbon atom. Broadband-decoupled 13 CNMR spectrum: The spectra provide information regarding the total number of carbon environments. DEPT (Distortionless enhancement by polarization transfer): i) DEPT -90: The spectrum exhibits signal only from CH group and no signals from CH 3 , CH 2 , CH and quaternary carbon (carbon with no protons). ii) DEPT -135: The spectrum exhibits CH 3 groups and CH groups as positive signals (pointing up); CH 2 groups appear as negative signals (pointing down) and quaternary carbon does not appear. The signals appear in each type of spectrum: To identify: The structure of given molecular formula C 8 H 16 .

Question

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Answer 1

Question

Chapter 13.SE, Problem 48AP

Interpretation Introduction

a)

Interpretation:

The structure of an given molecular formula C₈H₁₆ to be predicted using ¹³CNMR spectra.

Concept introduction:

The ¹³CNMR spectrum gives information on the different electronic environments of carbon. As like ¹HNMR, the number of signals generated in ¹³CNMR are predicted by performing symmetry operations (rotation or reflection symmetry). Only chemical shift values are reported in the spectrum but not the multiplicity and integration values because the coupling between two neighboring ¹³C - ¹³C nuclei are weakly involved due to the low abundance of ¹³C isotopes of carbon atom.

Broadband-decoupled ¹³CNMR spectrum: The spectra provide information regarding the total number of carbon environments.

DEPT (Distortionless enhancement by polarization transfer):

i) DEPT -90: The spectrum exhibits signal only from CH group and no signals from CH₃, CH₂, CH and quaternary carbon (carbon with no protons).

ii) DEPT -135: The spectrum exhibits CH₃ groups and CH groups as positive signals (pointing up); CH₂ groups appear as negative signals (pointing down) and quaternary carbon does not appear.

The signals appear in each type of spectrum:

To identify:

The structure of given molecular formula C₈H₁₆.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 2

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 3

The HDI calculation led to confirm about the presence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows five signals whereas the given molecular formula also has eight carbon atoms. Thus all the eight carbons have chemically different electronic environments showing signals.

i) The five signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene or Methine groups.

DEPT -90: Spectrum has no signals led to confirmation of no CH group in the structure.

DEPT -135 (gives signals of CH₂, CH₃ and C groups):

ii) The two positive signals indicate the presence of two methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The three negative signals indicate the presence of four methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -C-, four -CH₂

From the fragments (CH₃ + CH₃ + (CH₂)₅ + C = 16 protons) sixteen protons are obtained whereas the total number of protons from the molecular formula is also sixteen.

The possible structures are:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 4

The first structure possesses rotational symmetry and exhibits fewer signals in the spectrum and gets cancelled out.

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 5

Conclusion

The structure of a given molecular formula C₈H₁₆ is predicted using ¹³CNMR spectra.

Interpretation Introduction

b)

To identify:

The structure of given molecular formula C₃H₈O.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 6

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 7

The HDI calculation led to confirm about the absence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows three signals whereas the given molecular formula also has three carbon atoms. Thus all the three carbons have chemically different electronic environments showing signals.

i) The two signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene groups.

DEPT -90: Spectrum has no signals led to confirmation of no CH group in the structure.

DEPT -135 (gives signals of CH₂, CH₃ groups):

ii) The two positive signals indicate the presence of two methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The one negative signals indicate the presence of methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -CH₂

From the fragments (CH₃ + CH₃ + CH₂ = 8 protons) eight protons are obtained whereas the total number of protons from the molecular formula is also eight.

Conclusion

The structure of a given molecular formula C₃H₈O is predicted using ¹³CNMR spectra.

Interpretation Introduction

c)

To identify:

The structure of given molecular formula C₁₀H₂₀.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 8

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 9

The HDI calculation led to confirm about the presence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows six signals whereas the given molecular formula also has ten carbon atoms. Thus all the ten carbons have chemically different electronic environments showing signals.

i) The two signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene groups.

DEPT -90: Spectrum has signals led to confirmation of CH group in the structure.

DEPT -135 (gives signals of CH₂, C, CH₃ groups):

ii) The two positive signals indicate the presence of three methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The three negative signals indicate the presence of five methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -CH₂

From the fragments (CH₃)₃ + (CH₂)₅ + CH + C = 20 protons) twenty protons are obtained whereas the total number of protons from the molecular formula is also twenty.

Conclusion

The structure of a given molecular formula C₁₀H₂₀ is predicted using ¹³CNMR spectra.

Interpretation Introduction

d)

To identify:

The structure of given molecular formula C₆H₁₀.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 10

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 11

The HDI calculation led to confirm about the presence of a double bond or a ring. (two unsaturated degree).

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows six signals whereas the given molecular formula also has six carbon atoms. Thus all the six carbons have chemically different electronic environments showing signals.

i) The two signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene groups.

DEPT -90: Spectrum has signals led to confirmation of CH group in the structure.

DEPT -135 (gives signals of CH₂, C, CH₃ groups):

ii) The four positive signals indicate the presence of two methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The negative signals indicate the presence of methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -CH₂

From the fragments (CH₃)₂ + CH₂ + (CH)₂ + C = 10 protons) ten protons are obtained whereas the total number of protons from the molecular formula is also ten.

Conclusion

The structure of a given molecular formula C₆H₁₀ is predicted using ¹³CNMR spectra.

Interpretation Introduction

e)

To identify:

The structure of given molecular formula C₈H₁₆.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 12

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 13

The HDI calculation led to confirm about the presence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows four signals whereas the given molecular formula also has eight carbon atoms. Thus all the eight carbons have chemically different electronic environments showing signals.

i) The four signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene or Methine groups.

DEPT -90: Spectrum has no signals led to confirmation of CH group in the structure.

DEPT -135 (gives signals of CH₂, CH₃ and CH groups):

ii) The two positive signals indicate the presence of two methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The two negative signals indicate the presence of four methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -CH-, four -CH₂

From the fragments (CH₃ + CH₃ + (CH₂)₄ + (CH)₂ = 16 protons) sixteen protons are obtained whereas the total number of protons from the molecular formula is also sixteen.

Conclusion

The structure of a given molecular formula C₈H₁₆ is predicted using ¹³CNMR spectra.

Interpretation Introduction

f)

To identify:

The structure of given molecular formula C₆H₁₀O.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 14

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 15

The HDI calculation led to confirm about the presence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows four signals whereas the given molecular formula also has six carbon atoms. Thus all the six carbons have chemically different electronic environments showing signals.

i) The four signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene or Methine groups.

DEPT -135 (gives signals of CH₂, C groups):

ii) The two negative signals indicate the presence of four methylene groups; only methylene groups appear negative in the spectrum.

iii) So far the group of fragments obtained is

C=O, -C-, four -ch₂

From the fragments (CH₂)₅ + C = 10 protons) ten protons are obtained whereas the total number of protons from the molecular formula is also ten.

Conclusion

The structure of a given molecular formula C₆H₁₀O is predicted using ¹³CNMR spectra.

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13. (11pts total) Consider the arrows pointing at three different carbon-carbon bonds in the molecule depicted below. Bond B 2°C. +2°C. cleavage Bond A •CH3 + 26.← Cleavage 2°C. + Bond C +3°C• CH3 2C Cleavage E 2°C. 26. weakest bond Intact molecule Strongest 3°C 20. Gund Largest argest a. (2pts) Which bond between A-C is weakest? Which is strongest? Place answers in appropriate boxes. C Weakest bond A Produces Most Bond Strongest Bond Strongest Gund produces least stable radicals Weakest Stable radical b. (4pts) Consider the relative stability of all cleavage products that form when bonds A, B, AND C are homolytically cleaved/broken. Hint: cleavage products of bonds A, B, and C are all carbon radicals. i. Which ONE cleavage product is the most stable? A condensed or bond line representation is fine. 13°C. formed in bound C cleavage ii. Which ONE cleavage product is the least stable? A condensed or bond line representation is fine. • CH3 methyl radical Formed in Gund A Cleavage c.…

Answer 2

Question

Chapter 13.SE, Problem 48AP

Interpretation Introduction

a)

Interpretation:

The structure of an given molecular formula C₈H₁₆ to be predicted using ¹³CNMR spectra.

Concept introduction:

The ¹³CNMR spectrum gives information on the different electronic environments of carbon. As like ¹HNMR, the number of signals generated in ¹³CNMR are predicted by performing symmetry operations (rotation or reflection symmetry). Only chemical shift values are reported in the spectrum but not the multiplicity and integration values because the coupling between two neighboring ¹³C - ¹³C nuclei are weakly involved due to the low abundance of ¹³C isotopes of carbon atom.

Broadband-decoupled ¹³CNMR spectrum: The spectra provide information regarding the total number of carbon environments.

DEPT (Distortionless enhancement by polarization transfer):

i) DEPT -90: The spectrum exhibits signal only from CH group and no signals from CH₃, CH₂, CH and quaternary carbon (carbon with no protons).

ii) DEPT -135: The spectrum exhibits CH₃ groups and CH groups as positive signals (pointing up); CH₂ groups appear as negative signals (pointing down) and quaternary carbon does not appear.

The signals appear in each type of spectrum:

To identify:

The structure of given molecular formula C₈H₁₆.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 2

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 3

The HDI calculation led to confirm about the presence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows five signals whereas the given molecular formula also has eight carbon atoms. Thus all the eight carbons have chemically different electronic environments showing signals.

i) The five signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene or Methine groups.

DEPT -90: Spectrum has no signals led to confirmation of no CH group in the structure.

DEPT -135 (gives signals of CH₂, CH₃ and C groups):

ii) The two positive signals indicate the presence of two methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The three negative signals indicate the presence of four methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -C-, four -CH₂

From the fragments (CH₃ + CH₃ + (CH₂)₅ + C = 16 protons) sixteen protons are obtained whereas the total number of protons from the molecular formula is also sixteen.

The possible structures are:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 4

The first structure possesses rotational symmetry and exhibits fewer signals in the spectrum and gets cancelled out.

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 5

Conclusion

The structure of a given molecular formula C₈H₁₆ is predicted using ¹³CNMR spectra.

Interpretation Introduction

b)

To identify:

The structure of given molecular formula C₃H₈O.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 6

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 7

The HDI calculation led to confirm about the absence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows three signals whereas the given molecular formula also has three carbon atoms. Thus all the three carbons have chemically different electronic environments showing signals.

i) The two signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene groups.

DEPT -90: Spectrum has no signals led to confirmation of no CH group in the structure.

DEPT -135 (gives signals of CH₂, CH₃ groups):

ii) The two positive signals indicate the presence of two methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The one negative signals indicate the presence of methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -CH₂

From the fragments (CH₃ + CH₃ + CH₂ = 8 protons) eight protons are obtained whereas the total number of protons from the molecular formula is also eight.

Conclusion

The structure of a given molecular formula C₃H₈O is predicted using ¹³CNMR spectra.

Interpretation Introduction

c)

To identify:

The structure of given molecular formula C₁₀H₂₀.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 8

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 9

The HDI calculation led to confirm about the presence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows six signals whereas the given molecular formula also has ten carbon atoms. Thus all the ten carbons have chemically different electronic environments showing signals.

i) The two signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene groups.

DEPT -90: Spectrum has signals led to confirmation of CH group in the structure.

DEPT -135 (gives signals of CH₂, C, CH₃ groups):

ii) The two positive signals indicate the presence of three methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The three negative signals indicate the presence of five methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -CH₂

From the fragments (CH₃)₃ + (CH₂)₅ + CH + C = 20 protons) twenty protons are obtained whereas the total number of protons from the molecular formula is also twenty.

Conclusion

The structure of a given molecular formula C₁₀H₂₀ is predicted using ¹³CNMR spectra.

Interpretation Introduction

d)

To identify:

The structure of given molecular formula C₆H₁₀.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 10

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 11

The HDI calculation led to confirm about the presence of a double bond or a ring. (two unsaturated degree).

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows six signals whereas the given molecular formula also has six carbon atoms. Thus all the six carbons have chemically different electronic environments showing signals.

i) The two signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene groups.

DEPT -90: Spectrum has signals led to confirmation of CH group in the structure.

DEPT -135 (gives signals of CH₂, C, CH₃ groups):

ii) The four positive signals indicate the presence of two methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The negative signals indicate the presence of methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -CH₂

From the fragments (CH₃)₂ + CH₂ + (CH)₂ + C = 10 protons) ten protons are obtained whereas the total number of protons from the molecular formula is also ten.

Conclusion

The structure of a given molecular formula C₆H₁₀ is predicted using ¹³CNMR spectra.

Interpretation Introduction

e)

To identify:

The structure of given molecular formula C₈H₁₆.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 12

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 13

The HDI calculation led to confirm about the presence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows four signals whereas the given molecular formula also has eight carbon atoms. Thus all the eight carbons have chemically different electronic environments showing signals.

i) The four signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene or Methine groups.

DEPT -90: Spectrum has no signals led to confirmation of CH group in the structure.

DEPT -135 (gives signals of CH₂, CH₃ and CH groups):

ii) The two positive signals indicate the presence of two methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The two negative signals indicate the presence of four methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -CH-, four -CH₂

From the fragments (CH₃ + CH₃ + (CH₂)₄ + (CH)₂ = 16 protons) sixteen protons are obtained whereas the total number of protons from the molecular formula is also sixteen.

Conclusion

The structure of a given molecular formula C₈H₁₆ is predicted using ¹³CNMR spectra.

Interpretation Introduction

f)

To identify:

The structure of given molecular formula C₆H₁₀O.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 14

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 15

The HDI calculation led to confirm about the presence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows four signals whereas the given molecular formula also has six carbon atoms. Thus all the six carbons have chemically different electronic environments showing signals.

i) The four signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene or Methine groups.

DEPT -135 (gives signals of CH₂, C groups):

ii) The two negative signals indicate the presence of four methylene groups; only methylene groups appear negative in the spectrum.

iii) So far the group of fragments obtained is

C=O, -C-, four -ch₂

From the fragments (CH₂)₅ + C = 10 protons) ten protons are obtained whereas the total number of protons from the molecular formula is also ten.

Conclusion

The structure of a given molecular formula C₆H₁₀O is predicted using ¹³CNMR spectra.

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Answer 3

Question

Chapter 13.SE, Problem 48AP

Interpretation Introduction

a)

Interpretation:

The structure of an given molecular formula C₈H₁₆ to be predicted using ¹³CNMR spectra.

Concept introduction:

The ¹³CNMR spectrum gives information on the different electronic environments of carbon. As like ¹HNMR, the number of signals generated in ¹³CNMR are predicted by performing symmetry operations (rotation or reflection symmetry). Only chemical shift values are reported in the spectrum but not the multiplicity and integration values because the coupling between two neighboring ¹³C - ¹³C nuclei are weakly involved due to the low abundance of ¹³C isotopes of carbon atom.

Broadband-decoupled ¹³CNMR spectrum: The spectra provide information regarding the total number of carbon environments.

DEPT (Distortionless enhancement by polarization transfer):

i) DEPT -90: The spectrum exhibits signal only from CH group and no signals from CH₃, CH₂, CH and quaternary carbon (carbon with no protons).

ii) DEPT -135: The spectrum exhibits CH₃ groups and CH groups as positive signals (pointing up); CH₂ groups appear as negative signals (pointing down) and quaternary carbon does not appear.

The signals appear in each type of spectrum:

To identify:

The structure of given molecular formula C₈H₁₆.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 2

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 3

The HDI calculation led to confirm about the presence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows five signals whereas the given molecular formula also has eight carbon atoms. Thus all the eight carbons have chemically different electronic environments showing signals.

i) The five signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene or Methine groups.

DEPT -90: Spectrum has no signals led to confirmation of no CH group in the structure.

DEPT -135 (gives signals of CH₂, CH₃ and C groups):

ii) The two positive signals indicate the presence of two methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The three negative signals indicate the presence of four methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -C-, four -CH₂

From the fragments (CH₃ + CH₃ + (CH₂)₅ + C = 16 protons) sixteen protons are obtained whereas the total number of protons from the molecular formula is also sixteen.

The possible structures are:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 4

The first structure possesses rotational symmetry and exhibits fewer signals in the spectrum and gets cancelled out.

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 5

Conclusion

The structure of a given molecular formula C₈H₁₆ is predicted using ¹³CNMR spectra.

Interpretation Introduction

b)

To identify:

The structure of given molecular formula C₃H₈O.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 6

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 7

The HDI calculation led to confirm about the absence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows three signals whereas the given molecular formula also has three carbon atoms. Thus all the three carbons have chemically different electronic environments showing signals.

i) The two signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene groups.

DEPT -90: Spectrum has no signals led to confirmation of no CH group in the structure.

DEPT -135 (gives signals of CH₂, CH₃ groups):

ii) The two positive signals indicate the presence of two methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The one negative signals indicate the presence of methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -CH₂

From the fragments (CH₃ + CH₃ + CH₂ = 8 protons) eight protons are obtained whereas the total number of protons from the molecular formula is also eight.

Conclusion

The structure of a given molecular formula C₃H₈O is predicted using ¹³CNMR spectra.

Interpretation Introduction

c)

To identify:

The structure of given molecular formula C₁₀H₂₀.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 8

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 9

The HDI calculation led to confirm about the presence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows six signals whereas the given molecular formula also has ten carbon atoms. Thus all the ten carbons have chemically different electronic environments showing signals.

i) The two signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene groups.

DEPT -90: Spectrum has signals led to confirmation of CH group in the structure.

DEPT -135 (gives signals of CH₂, C, CH₃ groups):

ii) The two positive signals indicate the presence of three methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The three negative signals indicate the presence of five methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -CH₂

From the fragments (CH₃)₃ + (CH₂)₅ + CH + C = 20 protons) twenty protons are obtained whereas the total number of protons from the molecular formula is also twenty.

Conclusion

The structure of a given molecular formula C₁₀H₂₀ is predicted using ¹³CNMR spectra.

Interpretation Introduction

d)

To identify:

The structure of given molecular formula C₆H₁₀.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 10

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 11

The HDI calculation led to confirm about the presence of a double bond or a ring. (two unsaturated degree).

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows six signals whereas the given molecular formula also has six carbon atoms. Thus all the six carbons have chemically different electronic environments showing signals.

i) The two signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene groups.

DEPT -90: Spectrum has signals led to confirmation of CH group in the structure.

DEPT -135 (gives signals of CH₂, C, CH₃ groups):

ii) The four positive signals indicate the presence of two methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The negative signals indicate the presence of methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -CH₂

From the fragments (CH₃)₂ + CH₂ + (CH)₂ + C = 10 protons) ten protons are obtained whereas the total number of protons from the molecular formula is also ten.

Conclusion

The structure of a given molecular formula C₆H₁₀ is predicted using ¹³CNMR spectra.

Interpretation Introduction

e)

To identify:

The structure of given molecular formula C₈H₁₆.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 12

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 13

The HDI calculation led to confirm about the presence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows four signals whereas the given molecular formula also has eight carbon atoms. Thus all the eight carbons have chemically different electronic environments showing signals.

i) The four signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene or Methine groups.

DEPT -90: Spectrum has no signals led to confirmation of CH group in the structure.

DEPT -135 (gives signals of CH₂, CH₃ and CH groups):

ii) The two positive signals indicate the presence of two methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The two negative signals indicate the presence of four methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -CH-, four -CH₂

From the fragments (CH₃ + CH₃ + (CH₂)₄ + (CH)₂ = 16 protons) sixteen protons are obtained whereas the total number of protons from the molecular formula is also sixteen.

Conclusion

The structure of a given molecular formula C₈H₁₆ is predicted using ¹³CNMR spectra.

Interpretation Introduction

f)

To identify:

The structure of given molecular formula C₆H₁₀O.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 14

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 15

The HDI calculation led to confirm about the presence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows four signals whereas the given molecular formula also has six carbon atoms. Thus all the six carbons have chemically different electronic environments showing signals.

i) The four signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene or Methine groups.

DEPT -135 (gives signals of CH₂, C groups):

ii) The two negative signals indicate the presence of four methylene groups; only methylene groups appear negative in the spectrum.

iii) So far the group of fragments obtained is

C=O, -C-, four -ch₂

From the fragments (CH₂)₅ + C = 10 protons) ten protons are obtained whereas the total number of protons from the molecular formula is also ten.

Conclusion

The structure of a given molecular formula C₆H₁₀O is predicted using ¹³CNMR spectra.

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Answer 4

Question

Chapter 13.SE, Problem 48AP

Interpretation Introduction

a)

Interpretation:

The structure of an given molecular formula C₈H₁₆ to be predicted using ¹³CNMR spectra.

Concept introduction:

The ¹³CNMR spectrum gives information on the different electronic environments of carbon. As like ¹HNMR, the number of signals generated in ¹³CNMR are predicted by performing symmetry operations (rotation or reflection symmetry). Only chemical shift values are reported in the spectrum but not the multiplicity and integration values because the coupling between two neighboring ¹³C - ¹³C nuclei are weakly involved due to the low abundance of ¹³C isotopes of carbon atom.

Broadband-decoupled ¹³CNMR spectrum: The spectra provide information regarding the total number of carbon environments.

DEPT (Distortionless enhancement by polarization transfer):

i) DEPT -90: The spectrum exhibits signal only from CH group and no signals from CH₃, CH₂, CH and quaternary carbon (carbon with no protons).

ii) DEPT -135: The spectrum exhibits CH₃ groups and CH groups as positive signals (pointing up); CH₂ groups appear as negative signals (pointing down) and quaternary carbon does not appear.

The signals appear in each type of spectrum:

To identify:

The structure of given molecular formula C₈H₁₆.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 2

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 3

The HDI calculation led to confirm about the presence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows five signals whereas the given molecular formula also has eight carbon atoms. Thus all the eight carbons have chemically different electronic environments showing signals.

i) The five signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene or Methine groups.

DEPT -90: Spectrum has no signals led to confirmation of no CH group in the structure.

DEPT -135 (gives signals of CH₂, CH₃ and C groups):

ii) The two positive signals indicate the presence of two methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The three negative signals indicate the presence of four methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -C-, four -CH₂

From the fragments (CH₃ + CH₃ + (CH₂)₅ + C = 16 protons) sixteen protons are obtained whereas the total number of protons from the molecular formula is also sixteen.

The possible structures are:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 4

The first structure possesses rotational symmetry and exhibits fewer signals in the spectrum and gets cancelled out.

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 5

Conclusion

The structure of a given molecular formula C₈H₁₆ is predicted using ¹³CNMR spectra.

Interpretation Introduction

b)

To identify:

The structure of given molecular formula C₃H₈O.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 6

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 7

The HDI calculation led to confirm about the absence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows three signals whereas the given molecular formula also has three carbon atoms. Thus all the three carbons have chemically different electronic environments showing signals.

i) The two signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene groups.

DEPT -90: Spectrum has no signals led to confirmation of no CH group in the structure.

DEPT -135 (gives signals of CH₂, CH₃ groups):

ii) The two positive signals indicate the presence of two methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The one negative signals indicate the presence of methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -CH₂

From the fragments (CH₃ + CH₃ + CH₂ = 8 protons) eight protons are obtained whereas the total number of protons from the molecular formula is also eight.

Conclusion

The structure of a given molecular formula C₃H₈O is predicted using ¹³CNMR spectra.

Interpretation Introduction

c)

To identify:

The structure of given molecular formula C₁₀H₂₀.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 8

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 9

The HDI calculation led to confirm about the presence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows six signals whereas the given molecular formula also has ten carbon atoms. Thus all the ten carbons have chemically different electronic environments showing signals.

i) The two signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene groups.

DEPT -90: Spectrum has signals led to confirmation of CH group in the structure.

DEPT -135 (gives signals of CH₂, C, CH₃ groups):

ii) The two positive signals indicate the presence of three methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The three negative signals indicate the presence of five methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -CH₂

From the fragments (CH₃)₃ + (CH₂)₅ + CH + C = 20 protons) twenty protons are obtained whereas the total number of protons from the molecular formula is also twenty.

Conclusion

The structure of a given molecular formula C₁₀H₂₀ is predicted using ¹³CNMR spectra.

Interpretation Introduction

d)

To identify:

The structure of given molecular formula C₆H₁₀.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 10

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 11

The HDI calculation led to confirm about the presence of a double bond or a ring. (two unsaturated degree).

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows six signals whereas the given molecular formula also has six carbon atoms. Thus all the six carbons have chemically different electronic environments showing signals.

i) The two signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene groups.

DEPT -90: Spectrum has signals led to confirmation of CH group in the structure.

DEPT -135 (gives signals of CH₂, C, CH₃ groups):

ii) The four positive signals indicate the presence of two methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The negative signals indicate the presence of methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -CH₂

From the fragments (CH₃)₂ + CH₂ + (CH)₂ + C = 10 protons) ten protons are obtained whereas the total number of protons from the molecular formula is also ten.

Conclusion

The structure of a given molecular formula C₆H₁₀ is predicted using ¹³CNMR spectra.

Interpretation Introduction

e)

To identify:

The structure of given molecular formula C₈H₁₆.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 12

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 13

The HDI calculation led to confirm about the presence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows four signals whereas the given molecular formula also has eight carbon atoms. Thus all the eight carbons have chemically different electronic environments showing signals.

i) The four signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene or Methine groups.

DEPT -90: Spectrum has no signals led to confirmation of CH group in the structure.

DEPT -135 (gives signals of CH₂, CH₃ and CH groups):

ii) The two positive signals indicate the presence of two methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The two negative signals indicate the presence of four methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -CH-, four -CH₂

From the fragments (CH₃ + CH₃ + (CH₂)₄ + (CH)₂ = 16 protons) sixteen protons are obtained whereas the total number of protons from the molecular formula is also sixteen.

Conclusion

The structure of a given molecular formula C₈H₁₆ is predicted using ¹³CNMR spectra.

Interpretation Introduction

f)

To identify:

The structure of given molecular formula C₆H₁₀O.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 14

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 15

The HDI calculation led to confirm about the presence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows four signals whereas the given molecular formula also has six carbon atoms. Thus all the six carbons have chemically different electronic environments showing signals.

i) The four signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene or Methine groups.

DEPT -135 (gives signals of CH₂, C groups):

ii) The two negative signals indicate the presence of four methylene groups; only methylene groups appear negative in the spectrum.

iii) So far the group of fragments obtained is

C=O, -C-, four -ch₂

From the fragments (CH₂)₅ + C = 10 protons) ten protons are obtained whereas the total number of protons from the molecular formula is also ten.

Conclusion

The structure of a given molecular formula C₆H₁₀O is predicted using ¹³CNMR spectra.

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Answer 5

Chapter 13.SE, Problem 48AP

Interpretation Introduction

a)

Interpretation:

The structure of an given molecular formula C₈H₁₆ to be predicted using ¹³CNMR spectra.

Concept introduction:

The ¹³CNMR spectrum gives information on the different electronic environments of carbon. As like ¹HNMR, the number of signals generated in ¹³CNMR are predicted by performing symmetry operations (rotation or reflection symmetry). Only chemical shift values are reported in the spectrum but not the multiplicity and integration values because the coupling between two neighboring ¹³C - ¹³C nuclei are weakly involved due to the low abundance of ¹³C isotopes of carbon atom.

Broadband-decoupled ¹³CNMR spectrum: The spectra provide information regarding the total number of carbon environments.

DEPT (Distortionless enhancement by polarization transfer):

i) DEPT -90: The spectrum exhibits signal only from CH group and no signals from CH₃, CH₂, CH and quaternary carbon (carbon with no protons).

ii) DEPT -135: The spectrum exhibits CH₃ groups and CH groups as positive signals (pointing up); CH₂ groups appear as negative signals (pointing down) and quaternary carbon does not appear.

The signals appear in each type of spectrum:

To identify:

The structure of given molecular formula C₈H₁₆.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 2

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 3

The HDI calculation led to confirm about the presence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows five signals whereas the given molecular formula also has eight carbon atoms. Thus all the eight carbons have chemically different electronic environments showing signals.

i) The five signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene or Methine groups.

DEPT -90: Spectrum has no signals led to confirmation of no CH group in the structure.

DEPT -135 (gives signals of CH₂, CH₃ and C groups):

ii) The two positive signals indicate the presence of two methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The three negative signals indicate the presence of four methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -C-, four -CH₂

From the fragments (CH₃ + CH₃ + (CH₂)₅ + C = 16 protons) sixteen protons are obtained whereas the total number of protons from the molecular formula is also sixteen.

The possible structures are:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 4

The first structure possesses rotational symmetry and exhibits fewer signals in the spectrum and gets cancelled out.

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 5

Conclusion

The structure of a given molecular formula C₈H₁₆ is predicted using ¹³CNMR spectra.

Interpretation Introduction

b)

To identify:

The structure of given molecular formula C₃H₈O.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 6

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 7

The HDI calculation led to confirm about the absence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows three signals whereas the given molecular formula also has three carbon atoms. Thus all the three carbons have chemically different electronic environments showing signals.

i) The two signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene groups.

DEPT -90: Spectrum has no signals led to confirmation of no CH group in the structure.

DEPT -135 (gives signals of CH₂, CH₃ groups):

ii) The two positive signals indicate the presence of two methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The one negative signals indicate the presence of methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -CH₂

From the fragments (CH₃ + CH₃ + CH₂ = 8 protons) eight protons are obtained whereas the total number of protons from the molecular formula is also eight.

Conclusion

The structure of a given molecular formula C₃H₈O is predicted using ¹³CNMR spectra.

Interpretation Introduction

c)

To identify:

The structure of given molecular formula C₁₀H₂₀.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 8

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 9

The HDI calculation led to confirm about the presence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows six signals whereas the given molecular formula also has ten carbon atoms. Thus all the ten carbons have chemically different electronic environments showing signals.

i) The two signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene groups.

DEPT -90: Spectrum has signals led to confirmation of CH group in the structure.

DEPT -135 (gives signals of CH₂, C, CH₃ groups):

ii) The two positive signals indicate the presence of three methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The three negative signals indicate the presence of five methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -CH₂

From the fragments (CH₃)₃ + (CH₂)₅ + CH + C = 20 protons) twenty protons are obtained whereas the total number of protons from the molecular formula is also twenty.

Conclusion

The structure of a given molecular formula C₁₀H₂₀ is predicted using ¹³CNMR spectra.

Interpretation Introduction

d)

To identify:

The structure of given molecular formula C₆H₁₀.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 10

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 11

The HDI calculation led to confirm about the presence of a double bond or a ring. (two unsaturated degree).

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows six signals whereas the given molecular formula also has six carbon atoms. Thus all the six carbons have chemically different electronic environments showing signals.

i) The two signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene groups.

DEPT -90: Spectrum has signals led to confirmation of CH group in the structure.

DEPT -135 (gives signals of CH₂, C, CH₃ groups):

ii) The four positive signals indicate the presence of two methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The negative signals indicate the presence of methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -CH₂

From the fragments (CH₃)₂ + CH₂ + (CH)₂ + C = 10 protons) ten protons are obtained whereas the total number of protons from the molecular formula is also ten.

Conclusion

The structure of a given molecular formula C₆H₁₀ is predicted using ¹³CNMR spectra.

Interpretation Introduction

e)

To identify:

The structure of given molecular formula C₈H₁₆.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 12

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 13

The HDI calculation led to confirm about the presence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows four signals whereas the given molecular formula also has eight carbon atoms. Thus all the eight carbons have chemically different electronic environments showing signals.

i) The four signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene or Methine groups.

DEPT -90: Spectrum has no signals led to confirmation of CH group in the structure.

DEPT -135 (gives signals of CH₂, CH₃ and CH groups):

ii) The two positive signals indicate the presence of two methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The two negative signals indicate the presence of four methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -CH-, four -CH₂

From the fragments (CH₃ + CH₃ + (CH₂)₄ + (CH)₂ = 16 protons) sixteen protons are obtained whereas the total number of protons from the molecular formula is also sixteen.

Conclusion

The structure of a given molecular formula C₈H₁₆ is predicted using ¹³CNMR spectra.

Interpretation Introduction

f)

To identify:

The structure of given molecular formula C₆H₁₀O.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 14

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 15

The HDI calculation led to confirm about the presence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows four signals whereas the given molecular formula also has six carbon atoms. Thus all the six carbons have chemically different electronic environments showing signals.

i) The four signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene or Methine groups.

DEPT -135 (gives signals of CH₂, C groups):

ii) The two negative signals indicate the presence of four methylene groups; only methylene groups appear negative in the spectrum.

iii) So far the group of fragments obtained is

C=O, -C-, four -ch₂

From the fragments (CH₂)₅ + C = 10 protons) ten protons are obtained whereas the total number of protons from the molecular formula is also ten.

Conclusion

The structure of a given molecular formula C₆H₁₀O is predicted using ¹³CNMR spectra.

Answer 6

Chapter 13.SE, Problem 48AP

Interpretation Introduction

a)

Interpretation:

The structure of an given molecular formula C₈H₁₆ to be predicted using ¹³CNMR spectra.

Concept introduction:

The ¹³CNMR spectrum gives information on the different electronic environments of carbon. As like ¹HNMR, the number of signals generated in ¹³CNMR are predicted by performing symmetry operations (rotation or reflection symmetry). Only chemical shift values are reported in the spectrum but not the multiplicity and integration values because the coupling between two neighboring ¹³C - ¹³C nuclei are weakly involved due to the low abundance of ¹³C isotopes of carbon atom.

Broadband-decoupled ¹³CNMR spectrum: The spectra provide information regarding the total number of carbon environments.

DEPT (Distortionless enhancement by polarization transfer):

i) DEPT -90: The spectrum exhibits signal only from CH group and no signals from CH₃, CH₂, CH and quaternary carbon (carbon with no protons).

ii) DEPT -135: The spectrum exhibits CH₃ groups and CH groups as positive signals (pointing up); CH₂ groups appear as negative signals (pointing down) and quaternary carbon does not appear.

The signals appear in each type of spectrum:

To identify:

The structure of given molecular formula C₈H₁₆.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 2

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 3

The HDI calculation led to confirm about the presence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows five signals whereas the given molecular formula also has eight carbon atoms. Thus all the eight carbons have chemically different electronic environments showing signals.

i) The five signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene or Methine groups.

DEPT -90: Spectrum has no signals led to confirmation of no CH group in the structure.

DEPT -135 (gives signals of CH₂, CH₃ and C groups):

ii) The two positive signals indicate the presence of two methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The three negative signals indicate the presence of four methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -C-, four -CH₂

From the fragments (CH₃ + CH₃ + (CH₂)₅ + C = 16 protons) sixteen protons are obtained whereas the total number of protons from the molecular formula is also sixteen.

The possible structures are:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 4

The first structure possesses rotational symmetry and exhibits fewer signals in the spectrum and gets cancelled out.

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 5

Conclusion

The structure of a given molecular formula C₈H₁₆ is predicted using ¹³CNMR spectra.

Answer 7

Chapter 13.SE, Problem 48AP

Interpretation Introduction

a)

Interpretation:

The structure of an given molecular formula C₈H₁₆ to be predicted using ¹³CNMR spectra.

Concept introduction:

The ¹³CNMR spectrum gives information on the different electronic environments of carbon. As like ¹HNMR, the number of signals generated in ¹³CNMR are predicted by performing symmetry operations (rotation or reflection symmetry). Only chemical shift values are reported in the spectrum but not the multiplicity and integration values because the coupling between two neighboring ¹³C - ¹³C nuclei are weakly involved due to the low abundance of ¹³C isotopes of carbon atom.

Broadband-decoupled ¹³CNMR spectrum: The spectra provide information regarding the total number of carbon environments.

DEPT (Distortionless enhancement by polarization transfer):

i) DEPT -90: The spectrum exhibits signal only from CH group and no signals from CH₃, CH₂, CH and quaternary carbon (carbon with no protons).

ii) DEPT -135: The spectrum exhibits CH₃ groups and CH groups as positive signals (pointing up); CH₂ groups appear as negative signals (pointing down) and quaternary carbon does not appear.

The signals appear in each type of spectrum:

To identify:

The structure of given molecular formula C₈H₁₆.

Answer 8

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 2

Answer 9

Expert Solution

Answer 10

Expert Solution

Answer 11

Expert Solution

Answer 12

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 3

The HDI calculation led to confirm about the presence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows five signals whereas the given molecular formula also has eight carbon atoms. Thus all the eight carbons have chemically different electronic environments showing signals.

i) The five signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene or Methine groups.

DEPT -90: Spectrum has no signals led to confirmation of no CH group in the structure.

DEPT -135 (gives signals of CH₂, CH₃ and C groups):

ii) The two positive signals indicate the presence of two methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The three negative signals indicate the presence of four methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -C-, four -CH₂

From the fragments (CH₃ + CH₃ + (CH₂)₅ + C = 16 protons) sixteen protons are obtained whereas the total number of protons from the molecular formula is also sixteen.

The possible structures are:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 4

The first structure possesses rotational symmetry and exhibits fewer signals in the spectrum and gets cancelled out.

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 5

Answer 13

Conclusion

The structure of a given molecular formula C₈H₁₆ is predicted using ¹³CNMR spectra.

Answer 14

Interpretation Introduction

b)

To identify:

The structure of given molecular formula C₃H₈O.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 6

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 7

The HDI calculation led to confirm about the absence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows three signals whereas the given molecular formula also has three carbon atoms. Thus all the three carbons have chemically different electronic environments showing signals.

i) The two signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene groups.

DEPT -90: Spectrum has no signals led to confirmation of no CH group in the structure.

DEPT -135 (gives signals of CH₂, CH₃ groups):

ii) The two positive signals indicate the presence of two methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The one negative signals indicate the presence of methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -CH₂

From the fragments (CH₃ + CH₃ + CH₂ = 8 protons) eight protons are obtained whereas the total number of protons from the molecular formula is also eight.

Conclusion

The structure of a given molecular formula C₃H₈O is predicted using ¹³CNMR spectra.

Answer 15

Interpretation Introduction

b)

To identify:

The structure of given molecular formula C₃H₈O.

Answer 16

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 6

Answer 17

Expert Solution

Answer 18

Expert Solution

Answer 19

Expert Solution

Answer 20

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 7

The HDI calculation led to confirm about the absence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows three signals whereas the given molecular formula also has three carbon atoms. Thus all the three carbons have chemically different electronic environments showing signals.

i) The two signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene groups.

DEPT -90: Spectrum has no signals led to confirmation of no CH group in the structure.

DEPT -135 (gives signals of CH₂, CH₃ groups):

ii) The two positive signals indicate the presence of two methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The one negative signals indicate the presence of methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -CH₂

From the fragments (CH₃ + CH₃ + CH₂ = 8 protons) eight protons are obtained whereas the total number of protons from the molecular formula is also eight.

Answer 21

Conclusion

The structure of a given molecular formula C₃H₈O is predicted using ¹³CNMR spectra.

Answer 22

Interpretation Introduction

c)

To identify:

The structure of given molecular formula C₁₀H₂₀.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 8

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 9

The HDI calculation led to confirm about the presence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows six signals whereas the given molecular formula also has ten carbon atoms. Thus all the ten carbons have chemically different electronic environments showing signals.

i) The two signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene groups.

DEPT -90: Spectrum has signals led to confirmation of CH group in the structure.

DEPT -135 (gives signals of CH₂, C, CH₃ groups):

ii) The two positive signals indicate the presence of three methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The three negative signals indicate the presence of five methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -CH₂

From the fragments (CH₃)₃ + (CH₂)₅ + CH + C = 20 protons) twenty protons are obtained whereas the total number of protons from the molecular formula is also twenty.

Conclusion

The structure of a given molecular formula C₁₀H₂₀ is predicted using ¹³CNMR spectra.

Answer 23

Interpretation Introduction

c)

To identify:

The structure of given molecular formula C₁₀H₂₀.

Answer 24

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 8

Answer 25

Expert Solution

Answer 26

Expert Solution

Answer 27

Expert Solution

Answer 28

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 9

The HDI calculation led to confirm about the presence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows six signals whereas the given molecular formula also has ten carbon atoms. Thus all the ten carbons have chemically different electronic environments showing signals.

i) The two signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene groups.

DEPT -90: Spectrum has signals led to confirmation of CH group in the structure.

DEPT -135 (gives signals of CH₂, C, CH₃ groups):

ii) The two positive signals indicate the presence of three methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The three negative signals indicate the presence of five methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -CH₂

From the fragments (CH₃)₃ + (CH₂)₅ + CH + C = 20 protons) twenty protons are obtained whereas the total number of protons from the molecular formula is also twenty.

Answer 29

Conclusion

The structure of a given molecular formula C₁₀H₂₀ is predicted using ¹³CNMR spectra.

Answer 30

Interpretation Introduction

d)

To identify:

The structure of given molecular formula C₆H₁₀.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 10

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 11

The HDI calculation led to confirm about the presence of a double bond or a ring. (two unsaturated degree).

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows six signals whereas the given molecular formula also has six carbon atoms. Thus all the six carbons have chemically different electronic environments showing signals.

i) The two signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene groups.

DEPT -90: Spectrum has signals led to confirmation of CH group in the structure.

DEPT -135 (gives signals of CH₂, C, CH₃ groups):

ii) The four positive signals indicate the presence of two methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The negative signals indicate the presence of methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -CH₂

From the fragments (CH₃)₂ + CH₂ + (CH)₂ + C = 10 protons) ten protons are obtained whereas the total number of protons from the molecular formula is also ten.

Conclusion

The structure of a given molecular formula C₆H₁₀ is predicted using ¹³CNMR spectra.

Answer 31

Interpretation Introduction

d)

To identify:

The structure of given molecular formula C₆H₁₀.

Answer 32

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 10

Answer 33

Expert Solution

Answer 34

Expert Solution

Answer 35

Expert Solution

Answer 36

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 11

The HDI calculation led to confirm about the presence of a double bond or a ring. (two unsaturated degree).

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows six signals whereas the given molecular formula also has six carbon atoms. Thus all the six carbons have chemically different electronic environments showing signals.

i) The two signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene groups.

DEPT -90: Spectrum has signals led to confirmation of CH group in the structure.

DEPT -135 (gives signals of CH₂, C, CH₃ groups):

ii) The four positive signals indicate the presence of two methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The negative signals indicate the presence of methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -CH₂

From the fragments (CH₃)₂ + CH₂ + (CH)₂ + C = 10 protons) ten protons are obtained whereas the total number of protons from the molecular formula is also ten.

Answer 37

Conclusion

The structure of a given molecular formula C₆H₁₀ is predicted using ¹³CNMR spectra.

Answer 38

Interpretation Introduction

e)

To identify:

The structure of given molecular formula C₈H₁₆.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 12

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 13

The HDI calculation led to confirm about the presence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows four signals whereas the given molecular formula also has eight carbon atoms. Thus all the eight carbons have chemically different electronic environments showing signals.

i) The four signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene or Methine groups.

DEPT -90: Spectrum has no signals led to confirmation of CH group in the structure.

DEPT -135 (gives signals of CH₂, CH₃ and CH groups):

ii) The two positive signals indicate the presence of two methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The two negative signals indicate the presence of four methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -CH-, four -CH₂

From the fragments (CH₃ + CH₃ + (CH₂)₄ + (CH)₂ = 16 protons) sixteen protons are obtained whereas the total number of protons from the molecular formula is also sixteen.

Conclusion

The structure of a given molecular formula C₈H₁₆ is predicted using ¹³CNMR spectra.

Answer 39

Interpretation Introduction

e)

To identify:

The structure of given molecular formula C₈H₁₆.

Answer 40

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 12

Answer 41

Expert Solution

Answer 42

Expert Solution

Answer 43

Expert Solution

Answer 44

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 13

The HDI calculation led to confirm about the presence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows four signals whereas the given molecular formula also has eight carbon atoms. Thus all the eight carbons have chemically different electronic environments showing signals.

i) The four signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene or Methine groups.

DEPT -90: Spectrum has no signals led to confirmation of CH group in the structure.

DEPT -135 (gives signals of CH₂, CH₃ and CH groups):

ii) The two positive signals indicate the presence of two methyl groups as no signals appear in the DEPT -90 spectrum.

iii) The two negative signals indicate the presence of four methylene groups; only methylene groups appear negative in the spectrum.

iv) So far the group of fragments obtained is

Two -CH₃, -CH-, four -CH₂

From the fragments (CH₃ + CH₃ + (CH₂)₄ + (CH)₂ = 16 protons) sixteen protons are obtained whereas the total number of protons from the molecular formula is also sixteen.

Answer 45

Conclusion

The structure of a given molecular formula C₈H₁₆ is predicted using ¹³CNMR spectra.

Answer 46

Interpretation Introduction

f)

To identify:

The structure of given molecular formula C₆H₁₀O.

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 14

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 15

The HDI calculation led to confirm about the presence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows four signals whereas the given molecular formula also has six carbon atoms. Thus all the six carbons have chemically different electronic environments showing signals.

i) The four signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene or Methine groups.

DEPT -135 (gives signals of CH₂, C groups):

ii) The two negative signals indicate the presence of four methylene groups; only methylene groups appear negative in the spectrum.

iii) So far the group of fragments obtained is

C=O, -C-, four -ch₂

From the fragments (CH₂)₅ + C = 10 protons) ten protons are obtained whereas the total number of protons from the molecular formula is also ten.

Conclusion

The structure of a given molecular formula C₆H₁₀O is predicted using ¹³CNMR spectra.

Answer 47

Interpretation Introduction

f)

To identify:

The structure of given molecular formula C₆H₁₀O.

Answer 48

Expert Solution

Answer to Problem 48AP

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 14

Answer 49

Expert Solution

Answer 50

Expert Solution

Answer 51

Expert Solution

Answer 52

Explanation of Solution

Calculate HDI:

EP ORGANIC CHEMISTRY,24 MONTH-OWLV2, Chapter 13.SE, Problem 48AP , additional homework tip 15

The HDI calculation led to confirm about the presence of a double bond or a ring.

Interpret the given ¹³CNMR spectrum:

Broadband - decoupled spectrum:

The spectrum shows four signals whereas the given molecular formula also has six carbon atoms. Thus all the six carbons have chemically different electronic environments showing signals.

i) The four signals in the region of 0-50ppm indicate the sp³ hybridized carbon atoms which can be methyl / methylene or Methine groups.

DEPT -135 (gives signals of CH₂, C groups):

ii) The two negative signals indicate the presence of four methylene groups; only methylene groups appear negative in the spectrum.

iii) So far the group of fragments obtained is

C=O, -C-, four -ch₂

From the fragments (CH₂)₅ + C = 10 protons) ten protons are obtained whereas the total number of protons from the molecular formula is also ten.

Answer 53

Conclusion

The structure of a given molecular formula C₆H₁₀O is predicted using ¹³CNMR spectra.

Answer 54

Ch. 13.1 - Prob. 1P Ch. 13.1 - Prob. 2P Ch. 13.2 - Prob. 3P Ch. 13.3 - The following 1H NMR peaks were recorded on a...Ch. 13.3 - When the 1Î— NMR spectrum of acetone, CH3COCH3, is...Ch. 13.4 - Each of the following compounds has a single 1H...Ch. 13.4 - Identify the different types of protons in the...Ch. 13.5 - How many peaks would you expect in the 1H NMR...Ch. 13.6 - Predict the splitting patterns you would expect...Ch. 13.6 - Draw structures for compounds that meet the...

Concept explainers

Videos

Answer to Problem 48AP

Explanation of Solution

b)

To identify:

The structure of given molecular formula C₃H₈O.

Answer to Problem 48AP

Explanation of Solution

c)

To identify:

The structure of given molecular formula C₁₀H₂₀.

Answer to Problem 48AP

Explanation of Solution

d)

To identify:

The structure of given molecular formula C₆H₁₀.

Answer to Problem 48AP

Explanation of Solution

e)

To identify:

The structure of given molecular formula C₈H₁₆.

Answer to Problem 48AP

Explanation of Solution

f)

To identify:

The structure of given molecular formula C₆H₁₀O.

Answer to Problem 48AP

Explanation of Solution

Want to see more full solutions like this?

Chapter 13 Solutions

Concept explainers

Videos

Answer to Problem 48AP

Explanation of Solution

b) To identify: The structure of given molecular formula C3H8O.

Answer to Problem 48AP

Explanation of Solution

c) To identify: The structure of given molecular formula C10H20.

Answer to Problem 48AP

Explanation of Solution

d) To identify: The structure of given molecular formula C6H10.

Answer to Problem 48AP

Explanation of Solution

e) To identify: The structure of given molecular formula C8H16.

Answer to Problem 48AP

Explanation of Solution

f) To identify: The structure of given molecular formula C6H10O.

Answer to Problem 48AP

Explanation of Solution

Want to see more full solutions like this?

Chapter 13 Solutions

b)

To identify:

The structure of given molecular formula C₃H₈O.

c)

To identify:

The structure of given molecular formula C₁₀H₂₀.

d)

To identify:

The structure of given molecular formula C₆H₁₀.

e)

To identify:

The structure of given molecular formula C₈H₁₆.

f)

To identify:

The structure of given molecular formula C₆H₁₀O.