ORGANIC CHEMISTRY 1 TERM ACCESS
ORGANIC CHEMISTRY 1 TERM ACCESS
3rd Edition
ISBN: 9781119661511
Author: Klein
Publisher: WILEY
Question
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Chapter 21.7, Problem 45PTS

(a)

Interpretation Introduction

Interpretation:

To identify the major product in the given set of reactions when treated with Et2CuLi followed by mild acid.

Concept introduction:

The reaction between lithium dialkyl cuprate (Michael donor) which acts as a nucleophile for 1,4-conjugate addition to α, β- unsaturated compound (Michael acceptor) is known as Michael reaction.  Michael reaction is thermodynamically controlled.  A general scheme is shown below,

ORGANIC CHEMISTRY 1 TERM ACCESS, Chapter 21.7, Problem 45PTS , additional homework tip  1

The formed enolate when treated with alkyl halide installs the alkyl group in the α- position.

(b)

Interpretation Introduction

Interpretation:

To identify the major product in the given set of reactions when treated with Et2CuLi followed by mild acid.

Concept introduction:

The reaction between lithium dialkyl cuprate (Michael donor) which acts as a nucleophile for 1,4-conjugate addition to α, β- unsaturated compound (Michael acceptor) is known as Michael reaction.  Michael reaction is thermodynamically controlled.  A general scheme is shown below,

ORGANIC CHEMISTRY 1 TERM ACCESS, Chapter 21.7, Problem 45PTS , additional homework tip  2

The formed enolate when treated with alkyl halide installs the alkyl group in the α position.

Reduction of aldehyde to primary alcohol is done using LAH followed by acid work-up.

(c)

Interpretation Introduction

Interpretation:

To identify the major product in the given set of reactions when treated with Et2CuLi followed by mild acid.

Concept introduction:

The reaction between lithium dialkyl cuprate (Michael donor) which acts as a nucleophile for 1,4-conjugate addition to α, β- unsaturated compound (Michael acceptor) is known as Michael reaction.  Michael reaction is thermodynamically controlled.  A general scheme is shown below,

ORGANIC CHEMISTRY 1 TERM ACCESS, Chapter 21.7, Problem 45PTS , additional homework tip  3

The formed enolate when treated with alkyl halide installs the alkyl group in the α position.

Oxidation of the aldehyde with chromic acid gives the respective carboxylic acid which when treated with thionyl chloride gives the corresponding acid chloride.

(d)

Interpretation Introduction

Interpretation:

To identify the major product in the given set of reactions when treated with Et2CuLi followed by mild acid.

Concept introduction:

Hydrolysis of acetal with aqueous acid leads to ketone.

The reaction between lithium dialkyl cuprate (Michael donor) which acts as a nucleophile for 1,4-conjugate addition to α, β- unsaturated compound (Michael acceptor) is known as Michael reaction.  Michael reaction is thermodynamically controlled.  A general scheme is shown below,

ORGANIC CHEMISTRY 1 TERM ACCESS, Chapter 21.7, Problem 45PTS , additional homework tip  4

The formed enolate when treated with alkyl halide installs the alkyl group in the α position.

When ketone is treated with ethylene glycol, the keto group is converted into an acetal.

(e)

Interpretation Introduction

Interpretation:

To identify the major product in the given set of reactions when treated with Et2CuLi followed by mild acid.

Concept introduction:

Alcohol when treated with PCC undergoes oxidation to give aldehyde as the product.

The reaction between lithium dialkyl cuprate (Michael donor) which acts as a nucleophile for 1,4-conjugate addition to α, β- unsaturated compound (Michael acceptor) is known as Michael reaction.  Michael reaction is thermodynamically controlled.  A general scheme is shown below,

ORGANIC CHEMISTRY 1 TERM ACCESS, Chapter 21.7, Problem 45PTS , additional homework tip  5

The formed enolate when treated with alkyl halide installs the alkyl group in the α position.

Imine is formed when aldehyde is treated with a primary amine in acidic condition.

(f)

Interpretation Introduction

Interpretation:

To identify the major product in the given set of reactions when treated with Et2CuLi followed by mild acid.

Concept introduction:

Alcohol when treated with PCC undergoes oxidation to give aldehyde as the product.

The reaction between lithium dialkyl cuprate (Michael donor) which acts as a nucleophile for 1,4-conjugate addition to α, β- unsaturated compound (Michael acceptor) is known as Michael reaction.  Michael reaction is thermodynamically controlled.  A general scheme is shown below,

ORGANIC CHEMISTRY 1 TERM ACCESS, Chapter 21.7, Problem 45PTS , additional homework tip  6

The formed enolate when treated with alkyl halide installs the alkyl group in the α position.

Clemmenson reduction of aldehyde gives alkane as the final product

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Chapter 21 Solutions

ORGANIC CHEMISTRY 1 TERM ACCESS

Ch. 21.2 - Prob. 10CCCh. 21.2 - Prob. 11CCCh. 21.2 - Prob. 12CCCh. 21.2 - Prob. 13CCCh. 21.3 - Prob. 2LTSCh. 21.3 - Prob. 14PTSCh. 21.3 - Prob. 15PTSCh. 21.3 - Prob. 16ATSCh. 21.3 - Prob. 3LTSCh. 21.3 - Prob. 17PTSCh. 21.3 - Prob. 18ATSCh. 21.3 - Prob. 4LTSCh. 21.3 - Prob. 19PTSCh. 21.3 - Prob. 20ATSCh. 21.3 - Prob. 21CCCh. 21.3 - Prob. 22CCCh. 21.3 - Prob. 23CCCh. 21.4 - Prob. 24CCCh. 21.4 - Prob. 25CCCh. 21.4 - Prob. 26CCCh. 21.4 - Prob. 27CCCh. 21.4 - Prob. 28CCCh. 21.5 - Prob. 29CCCh. 21.5 - Prob. 30CCCh. 21.5 - Prob. 5LTSCh. 21.5 - Prob. 31PTSCh. 21.5 - Prob. 32ATSCh. 21.5 - Prob. 6LTSCh. 21.5 - Prob. 33PTSCh. 21.5 - Prob. 34ATSCh. 21.6 - Prob. 35CCCh. 21.6 - Prob. 36CCCh. 21.6 - Prob. 37CCCh. 21.6 - Prob. 7LTSCh. 21.6 - Prob. 38PTSCh. 21.6 - Prob. 39ATSCh. 21.6 - Prob. 40CCCh. 21.6 - Prob. 41CCCh. 21.7 - Prob. 8LTSCh. 21.7 - Prob. 42PTSCh. 21.7 - Prob. 43PTSCh. 21.7 - Prob. 9LTSCh. 21.7 - Prob. 45PTSCh. 21.7 - Prob. 46ATSCh. 21 - Prob. 47PPCh. 21 - Prob. 48PPCh. 21 - Prob. 49PPCh. 21 - Prob. 50PPCh. 21 - Prob. 51PPCh. 21 - Prob. 52PPCh. 21 - Prob. 53PPCh. 21 - Prob. 54PPCh. 21 - Prob. 55PPCh. 21 - Prob. 56PPCh. 21 - Prob. 57PPCh. 21 - Prob. 58PPCh. 21 - Prob. 59PPCh. 21 - Prob. 60PPCh. 21 - Prob. 61PPCh. 21 - Prob. 62PPCh. 21 - Prob. 63PPCh. 21 - Prob. 64PPCh. 21 - Prob. 65PPCh. 21 - Prob. 66PPCh. 21 - Prob. 67PPCh. 21 - Prob. 68PPCh. 21 - Prob. 69PPCh. 21 - Prob. 70PPCh. 21 - Prob. 71PPCh. 21 - Prob. 72PPCh. 21 - Prob. 73PPCh. 21 - Prob. 74PPCh. 21 - Prob. 75PPCh. 21 - Prob. 76PPCh. 21 - Prob. 77PPCh. 21 - Prob. 78PPCh. 21 - Prob. 79PPCh. 21 - Prob. 80PPCh. 21 - Prob. 81PPCh. 21 - Prob. 82PPCh. 21 - Prob. 83PPCh. 21 - Prob. 84PPCh. 21 - Prob. 85PPCh. 21 - Prob. 86PPCh. 21 - Prob. 87PPCh. 21 - Prob. 88PPCh. 21 - Prob. 89IPCh. 21 - Prob. 90IPCh. 21 - Prob. 91IPCh. 21 - Prob. 92IPCh. 21 - Prob. 93IPCh. 21 - Prob. 94IPCh. 21 - Prob. 95IPCh. 21 - Prob. 96IPCh. 21 - Prob. 97IPCh. 21 - Prob. 98IPCh. 21 - Prob. 99IPCh. 21 - Prob. 100IPCh. 21 - Prob. 101IPCh. 21 - Prob. 102IPCh. 21 - Prob. 103IPCh. 21 - Prob. 104IPCh. 21 - Prob. 105IPCh. 21 - Prob. 106IPCh. 21 - Prob. 107IPCh. 21 - Prob. 108IPCh. 21 - Prob. 109IPCh. 21 - Prob. 110IPCh. 21 - Prob. 111IPCh. 21 - Prob. 112IPCh. 21 - Prob. 113IPCh. 21 - Prob. 114IPCh. 21 - Prob. 115IPCh. 21 - Prob. 116CPCh. 21 - Prob. 117CPCh. 21 - Prob. 118CP
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