Organic Chemistry, Binder Ready Version
Organic Chemistry, Binder Ready Version
2nd Edition
ISBN: 9781118454312
Author: David R. Klein
Publisher: WILEY
Question
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Chapter 3, Problem 51PP

(a)

Interpretation Introduction

Interpretation:

Most acidic proton should be identified in the given compounds.

Concept introduction:

Acidic strength of the molecule depends on the stability of the Conjugate ion.

  • Conjugate ion is the ion, which is produced by de protonating the most acidic proton from the molecule.

This conjugate ion stability effected by four factors called ARIO (Atom Resonance Inductive effect Orbital) concept. If the conjugate anion is more stabilized, the acid considered as strong acid and the anion is weak base.

  • If negative charge located atom is larger enough to hold the negative charge, the anion attains stability.
  • If the anion is resonance stabilized, the corresponding acid is more acidic.
  • If withdrawing inductive effect is present near to the negative charge located position, acidity increases.

Organic Chemistry, Binder Ready Version, Chapter 3, Problem 51PP , additional homework tip  1 Hybridized orbital stabilizes the negative charge better than other hybridizations.

To identify: the most acidic proton in the given molecule.

(b)

Interpretation Introduction

Interpretation:

Most acidic proton should be identified in the given compounds.

Concept introduction:

Acidic strength of the molecule depends on the stability of the Conjugate ion.

  • Conjugate ion is the ion, which is produced by de protonating the most acidic proton from the molecule.

This conjugate ion stability effected by four factors called ARIO (Atom Resonance Inductive effect Orbital) concept. If the conjugate anion is more stabilized, the acid considered as strong acid and the anion is weak base.

  • If negative charge located atom is larger enough to hold the negative charge, the anion attains stability.
  • If the anion is resonance stabilized, the corresponding acid is more acidic.
  • If withdrawing inductive effect is present near to the negative charge located position, acidity increases.

Organic Chemistry, Binder Ready Version, Chapter 3, Problem 51PP , additional homework tip  2 Hybridized orbital stabilizes the negative charge better than other hybridizations.

To identify: the most acidic proton in the given molecule.

(c)

Interpretation Introduction

Interpretation:

Most acidic proton should be identified in the given compounds.

Concept introduction:

Acidic strength of the molecule depends on the stability of the Conjugate ion.

  • Conjugate ion is the ion, which is produced by de protonating the most acidic proton from the molecule.

This conjugate ion stability effected by four factors called ARIO (Atom Resonance Inductive effect Orbital) concept. If the conjugate anion is more stabilized, the acid considered as strong acid and the anion is weak base.

  • If negative charge located atom is larger enough to hold the negative charge, the anion attains stability.
  • If the anion is resonance stabilized, the corresponding acid is more acidic.
  • If withdrawing inductive effect is present near to the negative charge located position, acidity increases.

Organic Chemistry, Binder Ready Version, Chapter 3, Problem 51PP , additional homework tip  3 Hybridized orbital stabilizes the negative charge better than other hybridizations.

To identify: the most acidic proton in the given molecule.

(d)

Interpretation Introduction

Interpretation:

Most acidic proton should be identified in the given compounds.

Concept introduction:

Acidic strength of the molecule depends on the stability of the Conjugate ion.

  • Conjugate ion is the ion, which is produced by de protonating the most acidic proton from the molecule.

This conjugate ion stability effected by four factors called ARIO (Atom Resonance Inductive effect Orbital) concept. If the conjugate anion is more stabilized, the acid considered as strong acid and the anion is weak base.

  • If negative charge located atom is larger enough to hold the negative charge, the anion attains stability.
  • If the anion is resonance stabilized, the corresponding acid is more acidic.
  • If withdrawing inductive effect is present near to the negative charge located position, acidity increases.

Organic Chemistry, Binder Ready Version, Chapter 3, Problem 51PP , additional homework tip  4 Hybridized orbital stabilizes the negative charge better than other hybridizations.

To identify: the most acidic proton in the given molecule.

(e)

Interpretation Introduction

Interpretation:

Most acidic proton should be identified in the given compounds.

Concept introduction:

Acidic strength of the molecule depends on the stability of the Conjugate ion.

  • Conjugate ion is the ion, which is produced by de protonating the most acidic proton from the molecule.

This conjugate ion stability effected by four factors called ARIO (Atom Resonance Inductive effect Orbital) concept. If the conjugate anion is more stabilized, the acid considered as strong acid and the anion is weak base.

  • If negative charge located atom is larger enough to hold the negative charge, the anion attains stability.
  • If the anion is resonance stabilized, the corresponding acid is more acidic.
  • If withdrawing inductive effect is present near to the negative charge located position, acidity increases.

Organic Chemistry, Binder Ready Version, Chapter 3, Problem 51PP , additional homework tip  5 Hybridized orbital stabilizes the negative charge better than other hybridizations.

To identify: the most acidic proton in the given molecule.

(f)

Interpretation Introduction

Interpretation:

Most acidic proton should be identified in the given compounds.

Concept introduction:

Acidic strength of the molecule depends on the stability of the Conjugate ion.

  • Conjugate ion is the ion, which is produced by de protonating the most acidic proton from the molecule.

This conjugate ion stability effected by four factors called ARIO (Atom Resonance Inductive effect Orbital) concept. If the conjugate anion is more stabilized, the acid considered as strong acid and the anion is weak base.

  • If negative charge located atom is larger enough to hold the negative charge, the anion attains stability.
  • If the anion is resonance stabilized, the corresponding acid is more acidic.
  • If withdrawing inductive effect is present near to the negative charge located position, acidity increases.

Organic Chemistry, Binder Ready Version, Chapter 3, Problem 51PP , additional homework tip  6 Hybridized orbital stabilizes the negative charge better than other hybridizations.

To identify: the most acidic proton in the given molecule.

(g)

Interpretation Introduction

Interpretation:

Most acidic proton should be identified in the given compounds.

Concept introduction:

Acidic strength of the molecule depends on the stability of the Conjugate ion.

  • Conjugate ion is the ion, which is produced by de protonating the most acidic proton from the molecule.

This conjugate ion stability effected by four factors called ARIO (Atom Resonance Inductive effect Orbital) concept. If the conjugate anion is more stabilized, the acid considered as strong acid and the anion is weak base.

  • If negative charge located atom is larger enough to hold the negative charge, the anion attains stability.
  • If the anion is resonance stabilized, the corresponding acid is more acidic.
  • If withdrawing inductive effect is present near to the negative charge located position, acidity increases.

Organic Chemistry, Binder Ready Version, Chapter 3, Problem 51PP , additional homework tip  7 Hybridized orbital stabilizes the negative charge better than other hybridizations.

To identify: the most acidic proton in the given molecule.

(h)

Interpretation Introduction

Interpretation:

Most acidic proton should be identified in the given compounds.

Concept introduction:

Acidic strength of the molecule depends on the stability of the Conjugate ion.

  • Conjugate ion is the ion, which is produced by de protonating the most acidic proton from the molecule.

This conjugate ion stability effected by four factors called ARIO (Atom Resonance Inductive effect Orbital) concept. If the conjugate anion is more stabilized, the acid considered as strong acid and the anion is weak base.

  • If negative charge located atom is larger enough to hold the negative charge, the anion attains stability.
  • If the anion is resonance stabilized, the corresponding acid is more acidic.
  • If withdrawing inductive effect is present near to the negative charge located position, acidity increases.

Organic Chemistry, Binder Ready Version, Chapter 3, Problem 51PP , additional homework tip  8 Hybridized orbital stabilizes the negative charge better than other hybridizations.

To identify: the most acidic proton in the given molecule.

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redraw the flowchart with boxes and molecules written in them
Part I. a) Elucidate the structure of compound A using the following information. • mass spectrum: m+ = 102, m/2=57 312=29 • IR spectrum: 1002.5 % TRANSMITTANCE Ngg 50 40 30 20 90 80 70 60 MICRONS 5 8 9 10 12 13 14 15 16 19 1740 cm M 10 0 4000 3600 3200 2800 2400 2000 1800 1600 13 • CNMR 'H -NMR Peak 8 ppm (H) Integration multiplicity a 1.5 (3H) triplet b 1.3 1.5 (3H) triplet C 2.3 1 (2H) quartet d 4.1 1 (2H) quartet & ppm (c) 10 15 28 60 177 (C=0) b) Elucidate the structure of compound B using the following information 13C/DEPT NMR 150.9 MHz IIL 1400 WAVENUMBERS (CM-1) DEPT-90 DEPT-135 85 80 75 70 65 60 55 50 45 40 35 30 25 20 ppm 1200 1000 800 600 400
• Part II. a) Elucidate The structure of compound c w/ molecular formula C10 11202 and the following data below: • IR spectra % TRANSMITTANCE 1002.5 90 80 70 60 50 40 30 20 10 0 4000 3600 3200 2800 2400 2000 1800 1600 • Information from 'HAMR MICRONS 8 9 10 11 14 15 16 19 25 1400 WAVENUMBERS (CM-1) 1200 1000 800 600 400 peak 8 ppm Integration multiplicity a 2.1 1.5 (3H) Singlet b 3.6 1 (2H) singlet с 3.8 1.5 (3H) Singlet d 6.8 1(2H) doublet 7.1 1(2H) doublet Information from 13C-nmR Normal carbon 29ppm Dept 135 Dept -90 + NO peak NO peak 50 ppm 55 ppm + NO peak 114 ppm t 126 ppm No peak NO peak 130 ppm t + 159 ppm No peak NO peak 207 ppm по реак NO peak
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