Organic Chemistry 3rd.ed. Klein Evaluation/desk Copy
Organic Chemistry 3rd.ed. Klein Evaluation/desk Copy
3rd Edition
ISBN: 9781119320524
Author: Klein
Publisher: WILEY
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Chapter 22, Problem 45PP

(a)

Interpretation Introduction

Interpretation: Using a different type of reactions, 1-hexanol is to be prepared from hexyl amine, heptyl amine and pentyl amine

Concept Introduction: A number of transformations are used to prepare 1-hexanol.  Some of them are listed as follows:

  1. a) Alcohol on treatment with phosphorous tribromide gives alkyl bromide
  2. b) Alkyl bromide in azide synthesis produces primary amine
  3. c) Alkyl halide on treatment with sodium cyanide gives alkyl cyanide
  4. d) Cyanide on reduction gives alkyl amine with an increment of one carbon atom skeleton
  5. e) Alkene on ozonolysis produces carbonyl compounds
  6. f) Alkyl halides with strong base gives alkene
  7. g) Sodium cyanoborohydride is a strong reducing agent than sodium borohydride.  It reduces the carbonyl group into amine group in a rapid way.  So, it is called as reductive amination reactions.  Aldehyde or ketone group is reacted with ammonia in the presence of sodium cyanoborohydride as a reducing agent and a proton source in the reaction medium to produce primary amines.

Organic Chemistry 3rd.ed. Klein Evaluation/desk Copy, Chapter 22, Problem 45PP , additional homework tip  1

Using these concepts, we can transfer 1-hexanol into the given compounds.

(b)

Interpretation Introduction

Interpretation: Using a different type of reactions, 1-hexanol is to be prepared from hexyl amine, heptyl amine and pentyl amine

Concept Introduction: A number of transformations are used to prepare 1-hexanol.  Some of them are listed as follows:

  1. a) Alcohol on treatment with phosphorous tribromide gives alkyl bromide
  2. b) Alkyl bromide in azide synthesis produces primary amine
  3. c) Alkyl halide on treatment with sodium cyanide gives alkyl cyanide
  4. d) Cyanide on reduction gives alkyl amine with an increment of one carbon atom skeleton
  5. e) Alkene on ozonolysis produces carbonyl compounds
  6. f) Alkyl halides with strong base gives alkene
  7. g) Sodium cyanoborohydride is a strong reducing agent than sodium borohydride.  It reduces the carbonyl group into amine group in a rapid way.  So, it is called as reductive amination reactions.  Aldehyde or ketone group is reacted with ammonia in the presence of sodium cyanoborohydride as a reducing agent and a proton source in the reaction medium to produce primary amines.

Organic Chemistry 3rd.ed. Klein Evaluation/desk Copy, Chapter 22, Problem 45PP , additional homework tip  2

Using these concepts, we can transfer 1-hexanol into the given compounds.

(c)

Interpretation Introduction

Interpretation: Using a different type of reactions, 1-hexanol is to be prepared from hexyl amine, heptyl amine and pentyl amine

Concept Introduction: A number of transformations are used to prepare 1-hexanol.  Some of them are listed as follows:

  1. a) Alcohol on treatment with phosphorous tribromide gives alkyl bromide
  2. b) Alkyl bromide in azide synthesis produces primary amine
  3. c) Alkyl halide on treatment with sodium cyanide gives alkyl cyanide
  4. d) Cyanide on reduction gives alkyl amine with an increment of one carbon atom skeleton
  5. e) Alkene on ozonolysis produces carbonyl compounds
  6. f) Alkyl halides with strong base gives alkene
  7. g) Sodium cyanoborohydride is a strong reducing agent than sodium borohydride.  It reduces the carbonyl group into amine group in a rapid way.  So, it is called as reductive amination reactions.  Aldehyde or ketone group is reacted with ammonia in the presence of sodium cyanoborohydride as a reducing agent and a proton source in the reaction medium to produce primary amines.

Organic Chemistry 3rd.ed. Klein Evaluation/desk Copy, Chapter 22, Problem 45PP , additional homework tip  3

Using these concepts, we can transfer 1-hexanol into the given compounds.

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I have a question about this problem involving mechanisms and drawing curved arrows for acids and bases. I know we need to identify the nucleophile and electrophile, but are there different types of reactions? For instance, what about Grignard reagents and other types that I might not be familiar with? Can you help me with this? I want to identify the names of the mechanisms for problems 1-14, such as Gilman reagents and others. Are they all the same? Also, could you rewrite it so I can better understand? The handwriting is pretty cluttered. Additionally, I need to label the nucleophile and electrophile, but my main concern is whether those reactions differ, like the "Brønsted-Lowry acid-base mechanism, Lewis acid-base mechanism, acid-catalyzed mechanisms, acid-catalyzed reactions, base-catalyzed reactions, nucleophilic substitution mechanisms (SN1 and SN2), elimination reactions (E1 and E2), organometallic mechanisms, and so forth."

Chapter 22 Solutions

Organic Chemistry 3rd.ed. Klein Evaluation/desk Copy

Ch. 22.4 - Prob. 10CCCh. 22.4 - Prob. 11CCCh. 22.5 - Prob. 2LTSCh. 22.5 - Prob. 12PTSCh. 22.5 - Prob. 13ATSCh. 22.6 - Prob. 3LTSCh. 22.6 - Prob. 14PTSCh. 22.6 - Prob. 15ATSCh. 22.7 - Prob. 4LTSCh. 22.7 - Prob. 16PTSCh. 22.7 - Prob. 17PTSCh. 22.7 - Prob. 18PTSCh. 22.7 - Prob. 19ATSCh. 22.8 - Prob. 20CCCh. 22.8 - Prob. 21CCCh. 22.8 - Prob. 22CCCh. 22.9 - Prob. 5LTSCh. 22.9 - Prob. 23PTSCh. 22.9 - Prob. 24ATSCh. 22.10 - Prob. 25CCCh. 22.11 - Prob. 26CCCh. 22.11 - Prob. 6LTSCh. 22.11 - Prob. 27PTSCh. 22.11 - Prob. 28ATSCh. 22.12 - Prob. 29CCCh. 22.12 - Prob. 30CCCh. 22.13 - Prob. 31CCCh. 22.13 - Prob. 32CCCh. 22 - Prob. 33PPCh. 22 - Prob. 34PPCh. 22 - Prob. 35PPCh. 22 - Prob. 36PPCh. 22 - Prob. 37PPCh. 22 - Prob. 38PPCh. 22 - Prob. 39PPCh. 22 - Prob. 40PPCh. 22 - Prob. 41PPCh. 22 - Prob. 42PPCh. 22 - Prob. 43PPCh. 22 - Prob. 44PPCh. 22 - Prob. 45PPCh. 22 - Prob. 46PPCh. 22 - Prob. 47PPCh. 22 - Prob. 48PPCh. 22 - Prob. 49PPCh. 22 - Prob. 50PPCh. 22 - Prob. 51PPCh. 22 - Prob. 52PPCh. 22 - Prob. 53PPCh. 22 - Prob. 54PPCh. 22 - Prob. 55PPCh. 22 - Prob. 56PPCh. 22 - Prob. 57PPCh. 22 - Prob. 58PPCh. 22 - Prob. 59PPCh. 22 - Prob. 60PPCh. 22 - Prob. 61PPCh. 22 - Prob. 62PPCh. 22 - Prob. 63PPCh. 22 - Prob. 64PPCh. 22 - Prob. 65PPCh. 22 - Prob. 66PPCh. 22 - Prob. 67PPCh. 22 - Prob. 68PPCh. 22 - Prob. 69PPCh. 22 - Prob. 70PPCh. 22 - Prob. 71PPCh. 22 - Prob. 72PPCh. 22 - Prob. 73IPCh. 22 - Prob. 74IPCh. 22 - Prob. 75IPCh. 22 - Prob. 76IPCh. 22 - Prob. 77IPCh. 22 - Prob. 78IPCh. 22 - Prob. 79IPCh. 22 - Prob. 80IPCh. 22 - Prob. 81IPCh. 22 - Prob. 82IPCh. 22 - Prob. 83IPCh. 22 - Prob. 84IPCh. 22 - Prob. 85IPCh. 22 - Prob. 86IPCh. 22 - Prob. 87IPCh. 22 - Prob. 88IPCh. 22 - Prob. 89IPCh. 22 - Prob. 90IPCh. 22 - Prob. 91IPCh. 22 - Prob. 92IPCh. 22 - Prob. 93IPCh. 22 - Prob. 94IPCh. 22 - Prob. 95IPCh. 22 - Prob. 96CPCh. 22 - Prob. 97CPCh. 22 - Prob. 98CPCh. 22 - Prob. 99CP
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