ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 13, Problem 13.25P
Interpretation Introduction

(a)

Interpretation: The expected molecular ion for the given compound is to be determined.

Concept introduction: Molecular mass is the sum of the atomic weights of each constituent element multiplied by the number of atoms of that element. The molecular weight of compound is equal to the mass of the molecular ion.

Expert Solution
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Answer to Problem 13.25P

The structure of the given compound is,

ORGANIC CHEMISTRY, Chapter 13, Problem 13.25P , additional homework tip  1

The expected molecular ion peak of C6H6 is observed at m/z=78.

Explanation of Solution

The molecular formula of given compound is C6H6.

The m/z value of C6H6 is calculated as,

Mass of C6H6=(6×Mass of C atom+6×Mass of H atom)=(6×12+6×1)=(72 + 6)= 78 g/mol

The molecular weight of the compound is equal to the mass of the molecular ion.

Hence, the expected molecular ion peak of C6H6 is observed at m/z=78.

Conclusion

The expected molecular ion peak of C6H6 is observed at m/z=78.

Interpretation Introduction

(b)

Interpretation: The expected molecular ion for the given compound is to be determined.

Concept introduction: Molecular mass is the sum of the atomic weights of each constituent element multiplied by the number of atoms of that element. The molecular weight of compound is equal to the mass of the molecular ion.

Expert Solution
Check Mark

Answer to Problem 13.25P

The structure of the given compound is,

ORGANIC CHEMISTRY, Chapter 13, Problem 13.25P , additional homework tip  2

The expected molecular ion peak of C10H16 compound is observed at m/z=136

Explanation of Solution

The molecular formula of given compound is C10H16.

The m/z value of C10H16 is calculated as,

Mass of C10H16=(10×Mass of C atom+16×Mass of H atom)=(10×12+16×1)=(120+16)= 136 g/mol

The molecular weight of the compound is equal to the mass of the molecular ion.

Hence, the expected molecular ion peak of C10H16 compound is observed at m/z=136.

Conclusion

The expected molecular ion peak of C10H16 is observed at m/z=136.

Interpretation Introduction

(c)

Interpretation: The expected molecular ion for the given compound is to be determined.

Concept introduction: Molecular mass is the sum of the atomic weights of each constituent element multiplied by the number of atoms of that element. The molecular weight of compound is equal to the mass of the molecular ion.

Expert Solution
Check Mark

Answer to Problem 13.25P

The structure of the given compound is,

ORGANIC CHEMISTRY, Chapter 13, Problem 13.25P , additional homework tip  3

The expected molecular ion peak of C5H10O is observed at m/z=86.

Explanation of Solution

The molecular formula of given compound is C5H10O

The m/z value of C5H10O is calculated as,

Mass of C5H10O=(5×Mass of C atom+10×Mass of H atom +Mass of O atom)=(5×12+10×1+16)=(60+10+16)= 86 g/mol

The molecular weight of the compound is equal to the mass of the molecular ion.

The expected molecular ion peak of C5H10O is observed at m/z=86.

Conclusion

The expected molecular ion peak of C5H10O is observed at m/z=86.

Interpretation Introduction

(d)

Interpretation: The expected molecular ion for the given compound is to be determined.

Concept introduction: Molecular mass is the sum of the atomic weights of each constituent element multiplied by the number of atoms of that element. The molecular weight of compound is equal to the mass of the molecular ion.

Expert Solution
Check Mark

Answer to Problem 13.25P

The structure of the given compound is,

ORGANIC CHEMISTRY, Chapter 13, Problem 13.25P , additional homework tip  4

The larger molecular ion M peak is observed at m/z=106 (C5H1135Cl) and small M+2 peak is observed at m/z=108 (C5H1137Cl).

Explanation of Solution

The molecular formula of given compound is C5H11Cl. Chlorine has two isotopes 35Cl and 37Cl.

The m/z value of C5H1135Cl is calculated as follows.

Mass of C5H1135Cl=(5×Mass of C atom+11×Mass of H atom + Mass of 35Cl atom)=(5×12+11×1+ 35 )=(60+11+35)= 106 g/mol

The m/z value of C5H1137Cl is calculated as follows.

Mass of C5H1137Cl=(5×Mass of C atom+11×Mass of H atom + Mass of 37Cl atom)=(5×12+11×1+ 37 )=(60+11+37)= 108 g/mol

The molecular weight of the compound is equal to the mass of the molecular ion.

Hence, the larger molecular ion M peak is observed at m/z=106 (C5H1135Cl) and small M+2 peak is observed at m/z=108 (C5H1137Cl).

Conclusion

The larger molecular ion M is observed peak at m/z=106 (C5H1135Cl) and M+2 is observed small peak at m/z=108 (C5H1137Cl).

Interpretation Introduction

(e)

Interpretation: The expected molecular ion for the given compound is to be determined.

Concept introduction: Molecular mass is the sum of the atomic weights of each constituent element multiplied by the number of atoms of that element. The molecular weight of compound is equal to the mass of the molecular ion.

Expert Solution
Check Mark

Answer to Problem 13.25P

The structure of the given compound is,

ORGANIC CHEMISTRY, Chapter 13, Problem 13.25P , additional homework tip  5

The larger molecular ion M peak is observed at m/z=192 (C8H1779Br) and small M+2 peak is observed at m/z=194 (C8H1781Br).

Explanation of Solution

The molecular formula of given compound is C8H17Br. Bromine atom has two isotopes 79Br and 81Br.

The m/z value of C8H1779Br is calculated as follows.

Mass of C8H1779Br=(8×Mass of C atom+17×Mass of H atom + Mass of Br atom)=(8×12+17×1+ 79)=(96 + 17+79)= 192

The m/z value of C8H1781Br is calculated as follows.

Mass of C8H1781Br=(8×Mass of C atom+17×Mass of H atom + Mass of Br atom)=(8×12+17×1+ 81)=(96 + 17+81)= 194

The molecular weight of the compound is equal to the mass of the molecular ion.

Hence, the larger molecular ion M peak is observed at m/z=192 (C8H1779Br) and small M+2 peak is observed at m/z=194 (C8H1781Br).

Conclusion

The larger molecular ion M peak is observed at m/z=192 (C8H1779Br) and small M+2 peak is observed at m/z=194 (C8H1781Br).

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Chapter 13 Solutions

ORGANIC CHEMISTRY

Ch. 13 - Benzene, toluene, and p-xylene BTX are often added...Ch. 13 - Prob. 13.12PCh. 13 - Prob. 13.13PCh. 13 - Prob. 13.14PCh. 13 - Prob. 13.15PCh. 13 - How do the IR spectra of the isomers cyclopentane...Ch. 13 - Problem 13.17 How do the three isomers of...Ch. 13 - Problem 13.18 What functional groups are...Ch. 13 - Problem-13.19 What are the major IR absorptions in...Ch. 13 - Problem-13.20 What are the major IR absorptions in...Ch. 13 - Problem-13.21 Which of the following possible...Ch. 13 - Problem-13.22 Propose structures consistent with...Ch. 13 - 13.23 What major IR absorptions are present above ...Ch. 13 - Problem-13.24 The mass spectrum of the following...Ch. 13 - Prob. 13.25PCh. 13 - Which compound gives a molecular ion at m/z= 122,...Ch. 13 - Propose two molecular formulas for each molecular...Ch. 13 - Propose four possible structures for a hydrocarbon...Ch. 13 - Problem-13.29 What is the molecular formula for...Ch. 13 - Problem-13.30 Propose a molecular formula for rose...Ch. 13 - 13.31 Match each structure to its mass spectrum Ch. 13 - 13.32 Propose two possible structures for a...Ch. 13 - 13.33 What cations are formed in the mass...Ch. 13 - 13.34 and have the same molecular ion in the...Ch. 13 - 13.35 For each compound, assign likely...Ch. 13 - Prob. 13.36PCh. 13 - 13.37 Propose a structure consistent with each...Ch. 13 - 13.38 A low-resolution mass spectrum of the...Ch. 13 - 13.39 Primary alcohols often show a peak in their...Ch. 13 - 13.40 Like alcohols, ethers undergo α cleavage by...Ch. 13 - 13.41 Which of the highlighted bonds absorbs at...Ch. 13 - 13.42 What major IR absorptions are present above ...Ch. 13 - 13.43 How would each of the following pairs of...Ch. 13 - 13.44 Morphine, heroin, and oxycodone are three...Ch. 13 - 13.45 Reduction of cyclohex-2-enone can yield...Ch. 13 - Prob. 13.46PCh. 13 - 13.47 Match each compound to its IR spectrum Ch. 13 - 13.48 Propose possible structures consistent with...Ch. 13 - A chiral hydrocarbon X exhibits a molecular ion at...Ch. 13 - 13.50 A chiral compound has a strong absorption...Ch. 13 - 13.51 Treatment of benzoic acid with followed by...Ch. 13 - 13.52 Treatment of benzaldehyde with in aqueous ...Ch. 13 - Prob. 13.53PCh. 13 - 13.54 Reaction of 2-methylpropanoic acid with ...Ch. 13 - 13.55 Reaction of pentanoyl chloride with lithium...Ch. 13 - Prob. 13.56PCh. 13 - 13.57 Treatment of anisole with and forms P,...Ch. 13 - 13.58 Reaction of with forms compound ,...Ch. 13 - Problem-13.59 The carbonyl absorption of an amide...Ch. 13 - Prob. 13.60PCh. 13 - Problem-13.61 Explain why a ketone carbonyl...Ch. 13 - 13.62 Oxidation of citronellol, a constituent of...
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