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 22, Problem 63PP

(a)

Interpretation Introduction

Interpretation:

To draw the enolate formed when a set of given compounds is treated with LDA.

Concept introduction:

When an base deprotonates a carbonyl compound in its α position and enolate is formed.  If LDA is used as base for deprotonation the hydrogen is completely removed as it is a strong base.

Please bear in mind that LDA is a strong, sterically hindered base, so it deprotonates the less substituted α carbon.

Organic Chemistry, Binder Ready Version, Chapter 22, Problem 63PP , additional homework tip  1

To draw : To draw the enolate of the given compound when treated with LDA

(b)

Interpretation Introduction

Interpretation:

To draw the enolate formed when a set of given compounds is treated with LDA.

Concept introduction:

When an base deprotonates a carbonyl compound in its α position and enolate is formed.  If LDA is used as base for deprotonation the hydrogen is completely removed as it is a strong base.

Please bear in mind that LDA is a strong, sterically hindered base, so it deprotonates the less substituted α carbon.

Organic Chemistry, Binder Ready Version, Chapter 22, Problem 63PP , additional homework tip  2

To draw : To draw the enolate of the given compound when treated with LDA

(c)

Interpretation Introduction

Interpretation:

To draw the enolate formed when a set of given compounds is treated with LDA.

Concept introduction:

When an base deprotonates a carbonyl compound in its α position and enolate is formed.  If LDA is used as base for deprotonation the hydrogen is completely removed as it is a strong base.

Please bear in mind that LDA is a strong, sterically hindered base, so it deprotonates the less substituted α carbon.

Organic Chemistry, Binder Ready Version, Chapter 22, Problem 63PP , additional homework tip  3

To draw : To draw the enolate of the given compound when treated with LDA

(d)

Interpretation Introduction

Interpretation:

To draw the enolate formed when a set of given compounds is treated with LDA.

Concept introduction:

When an base deprotonates a carbonyl compound in its α position and enolate is formed.  If LDA is used as base for deprotonation the hydrogen is completely removed as it is a strong base.

Please bear in mind that LDA is a strong, sterically hindered base, so it deprotonates the less substituted α carbon.

Organic Chemistry, Binder Ready Version, Chapter 22, Problem 63PP , additional homework tip  4

To draw : To draw the enolate of the given compound when treated with LDA

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Part V. Label ad match the carbons in compounds Jane and Diane w/ the corresponding peak no. in the Spectra (Note: use the given peak no. To label the carbons, other peak no are intentionally omitted) 7 4 2 -0.13 -0.12 -0.11 -0.10 -0.08 8 CI Jane 1 -0.09 5 210 200 190 180 170 160 150 140 130 120 110 100 -8 90 f1 (ppm) 11 8 172.4 172.0 f1 (ppr HO CI NH Diane 7 3 11 80 80 -80 -R 70 60 60 2 5 -8 50 40 8. 170 160 150 140 130 120 110 100 90 -0 80 70 20 f1 (ppm) 15 30 -20 20 -60 60 -0.07 -0.06 -0.05 -0.04 -0.03 -0.02 -0.01 -0.00 -0.01 10 -0.17 16 15 56 16 -0.16 -0.15 -0.14 -0.13 -0.12 -0.11 -0.10 -0.09 -0.08 -0.07 -0.06 -0.05 -0.04 17.8 17.6 17.4 17.2 17.0 f1 (ppm) -0.03 -0.02 550 106 40 30 20 20 -0.01 -0.00 F-0.01 10 0

Chapter 22 Solutions

Organic Chemistry, Binder Ready Version

Ch. 22.2 - Prob. 10CCCh. 22.2 - Prob. 11CCCh. 22.2 - Prob. 12CCCh. 22.2 - Prob. 13CCCh. 22.2 - Prob. 14CCCh. 22.3 - Prob. 2LTSCh. 22.3 - Prob. 15PTSCh. 22.3 - Prob. 16PTSCh. 22.3 - Prob. 17ATSCh. 22.3 - Prob. 18ATSCh. 22.3 - Prob. 19ATSCh. 22.3 - Prob. 3LTSCh. 22.3 - Prob. 20PTSCh. 22.3 - Prob. 21ATSCh. 22.3 - Prob. 22ATSCh. 22.3 - Prob. 4LTSCh. 22.3 - Prob. 23PTSCh. 22.3 - Prob. 24ATSCh. 22.3 - Prob. 25CCCh. 22.3 - Prob. 26CCCh. 22.3 - Prob. 27CCCh. 22.4 - Prob. 28CCCh. 22.4 - Prob. 29CCCh. 22.4 - Prob. 30CCCh. 22.4 - Prob. 31CCCh. 22.4 - Prob. 32CCCh. 22.5 - Prob. 33CCCh. 22.5 - Prob. 34CCCh. 22.5 - Prob. 5LTSCh. 22.5 - Prob. 35PTSCh. 22.5 - Prob. 36ATSCh. 22.5 - Prob. 37ATSCh. 22.5 - Prob. 38ATSCh. 22.5 - Prob. 6LTSCh. 22.5 - Prob. 39PTSCh. 22.5 - Prob. 40ATSCh. 22.5 - Prob. 41ATSCh. 22.5 - Prob. 42ATSCh. 22.5 - Prob. 43ATSCh. 22.6 - Prob. 44CCCh. 22.6 - Prob. 45CCCh. 22.6 - Prob. 46CCCh. 22.6 - Prob. 7LTSCh. 22.6 - Prob. 47PTSCh. 22.6 - Prob. 48ATSCh. 22.6 - Prob. 49CCCh. 22.6 - Prob. 50CCCh. 22.7 - Prob. 8LTSCh. 22.7 - Prob. 51PTSCh. 22.7 - Prob. 52PTSCh. 22.7 - Prob. 53ATSCh. 22.7 - Prob. 9LTSCh. 22.7 - Prob. 54PTSCh. 22.7 - Prob. 55ATSCh. 22.7 - Prob. 56ATSCh. 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. 73PPCh. 22 - Prob. 74PPCh. 22 - Prob. 75PPCh. 22 - Prob. 76PPCh. 22 - Prob. 77PPCh. 22 - Prob. 78PPCh. 22 - Prob. 79PPCh. 22 - Prob. 80PPCh. 22 - Prob. 81PPCh. 22 - Prob. 82PPCh. 22 - Prob. 83PPCh. 22 - Prob. 84PPCh. 22 - Prob. 85PPCh. 22 - Prob. 86PPCh. 22 - Prob. 87PPCh. 22 - Prob. 88PPCh. 22 - Prob. 89PPCh. 22 - Prob. 90PPCh. 22 - Prob. 91PPCh. 22 - Prob. 92PPCh. 22 - Prob. 93PPCh. 22 - Prob. 94PPCh. 22 - Prob. 95PPCh. 22 - Prob. 96PPCh. 22 - Prob. 97PPCh. 22 - Prob. 98PPCh. 22 - Prob. 99PPCh. 22 - Prob. 100IPCh. 22 - Prob. 101IPCh. 22 - Prob. 102IPCh. 22 - Prob. 103IPCh. 22 - Prob. 104IPCh. 22 - Prob. 105IPCh. 22 - Prob. 106IPCh. 22 - Prob. 107IPCh. 22 - Prob. 108IPCh. 22 - Prob. 109IPCh. 22 - Prob. 110IPCh. 22 - Prob. 111IPCh. 22 - Prob. 112IP
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