Organic Chemistry
Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 20, Problem 20.34P

Draw the product when each compound is treated with either ( CH 3 ) 2 CuLi , followed by H 2 O , or HC CLi , followed by H 2 O .

a. Chapter 20, Problem 20.34P, Problem 20.34 Draw the product when each compound is treated with either , followed by , or , , example  1 b. Chapter 20, Problem 20.34P, Problem 20.34 Draw the product when each compound is treated with either , followed by , or , , example  2 c. Chapter 20, Problem 20.34P, Problem 20.34 Draw the product when each compound is treated with either , followed by , or , , example  3

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation: The product formed by the treatment of given compound with either (CH3)2CuLi followed by H2O or HCCLi followed by H2O is to be stated.

Concept introduction: Organometallic reagents like RLi,RMgX and R2CuLi are the source of R, which acts as a nucleophile. Organocuprate reagent form 1,4-addition product on reaction with α,β-unsaturated carbonyl compound whereas organolithium and Grignard reagent form 1,2-addition product on reaction with α,β-unsaturated carbonyl compound.

Answer to Problem 20.34P

The product formed by the treatment of given compound with (CH3)2CuLi followed by H2O and HCCLi followed by H2O is,

Organic Chemistry, Chapter 20, Problem 20.34P , additional homework tip  1

Figure 1

Explanation of Solution

The given reagents are organocuprate ((CH3)2CuLi) and organolithium (HCCLi). Organocuprate reagent form 1,4-addition product whereas organolithium reagent form 1,2-addition product on reaction with α,β-unsaturated carbonyl compound.

The product formed by the reaction of (CH3)2CuLi with given α,β-unsaturated carbonyl compound is 1,4-addition product as shown in Figure 2.

Organic Chemistry, Chapter 20, Problem 20.34P , additional homework tip  2

Figure 2

The product formed by the reaction of HCCLi with given α,β-unsaturated carbonyl compound is 1,4-addition product as shown in Figure 3.

Organic Chemistry, Chapter 20, Problem 20.34P , additional homework tip  3

Figure 3

Conclusion

The product formed by the treatment of given compound with (CH3)2CuLi followed by H2O and HCCLi followed by H2O is shown in Figure 2 and Figure 3.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The product formed by the treatment of given compound with either (CH3)2CuLi followed by H2O or HCCLi followed by H2O is to be stated.

Concept introduction: Organometallic reagents like RLi,RMgX and R2CuLi are the source of R, which acts as a nucleophile. Organocuprate reagent form 1,4-addition product on reaction with α,β-unsaturated carbonyl compound whereas organolithium and Grignard reagent form 1,2-addition product on reaction with α,β-unsaturated carbonyl compound.

Answer to Problem 20.34P

The product formed by the treatment of given compound with (CH3)2CuLi followed by H2O and HCCLi followed by H2O is,

Organic Chemistry, Chapter 20, Problem 20.34P , additional homework tip  4

Figure 4

Explanation of Solution

The given reagents are organocuprate ((CH3)2CuLi) and organolithium (HCCLi). Organocuprate reagent form 1,4-addition product whereas organolithium reagent form 1,2-addition product on reaction with α,β-unsaturated carbonyl compound.

The product formed by the reaction of (CH3)2CuLi with given α,β-unsaturated carbonyl compound is 1,4-addition product as shown in Figure 5.

Organic Chemistry, Chapter 20, Problem 20.34P , additional homework tip  5

Figure 5

The product formed by the reaction of HCCLi with given α,β-unsaturated carbonyl compound is 1,4-addition product as shown in Figure 6.

Organic Chemistry, Chapter 20, Problem 20.34P , additional homework tip  6

Figure 6

Conclusion

The product formed by the treatment of given compound with (CH3)2CuLi followed by H2O and HCCLi followed by H2O is shown in Figure 5 and Figure 6.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The product formed by the treatment of given compound with either (CH3)2CuLi followed by H2O or HCCLi followed by H2O is to be stated.

Concept introduction: Organometallic reagents like RLi,RMgX and R2CuLi are the source of R, which acts as a nucleophile. Organocuprate reagent form 1,4-addition product on reaction with α,β-unsaturated carbonyl compound whereas organolithium and Grignard reagent form 1,2-addition product on reaction with α,β-unsaturated carbonyl compound.

Answer to Problem 20.34P

The product formed by the treatment of given compound with (CH3)2CuLi followed by H2O and HCCLi followed by H2O is,

Organic Chemistry, Chapter 20, Problem 20.34P , additional homework tip  7

Figure 7

Explanation of Solution

The given reagents are organocuprate ((CH3)2CuLi) and organolithium (HCCLi). Organocuprate reagent form 1,4-addition product whereas organolithium reagent form 1,2-addition product on reaction with α,β-unsaturated carbonyl compound.

The product formed by the reaction of (CH3)2CuLi with given α,β-unsaturated carbonyl compound is 1,4-addition product as shown in Figure 2.

Organic Chemistry, Chapter 20, Problem 20.34P , additional homework tip  8

Figure 8

The product formed by the reaction of HCCLi with given α,β-unsaturated carbonyl compound is 1,4-addition product as shown in Figure 3.

Organic Chemistry, Chapter 20, Problem 20.34P , additional homework tip  9

Figure 9

Conclusion

The product formed by the treatment of given compound with (CH3)2CuLi followed by H2O and HCCLi followed by H2O is shown in Figure 8 and Figure 9.

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Chapter 20 Solutions

Organic Chemistry

Ch. 20 - Prob. 20.11PCh. 20 - Problem 20.12 Draw the products formed from ...Ch. 20 - Prob. 20.13PCh. 20 - Prob. 20.14PCh. 20 - Prob. 20.15PCh. 20 - Problem-20.16 Review the oxidation reactions using...Ch. 20 - Problem-20.17 Write the step(s) needed to convert ...Ch. 20 - Problem-20.18 Oct-1-yne reacts rapidly with ,...Ch. 20 - Prob. 20.19PCh. 20 - Prob. 20.20PCh. 20 - Problem 20.21 Draw the product of each reaction. ...Ch. 20 - Problem 20.22 Draw the products (including...Ch. 20 - Problem 20.23 What Grignard reagent and carbonyl...Ch. 20 - Problem 20.24 Linalool (the Chapter 9 opening...Ch. 20 - Problem 20.25 What Grignard reagent and carbonyl...Ch. 20 - Prob. 20.26PCh. 20 - Draw the products formed when each compound is...Ch. 20 - Problem 20.28 What ester and Grignard reagent are...Ch. 20 - Prob. 20.29PCh. 20 - Problem 20.30 What reagent is needed to convert ...Ch. 20 - Prob. 20.31PCh. 20 - What carboxylic acid formed from each alkyl halide...Ch. 20 - Prob. 20.33PCh. 20 - Problem 20.34 Draw the product when each compound...Ch. 20 - Problem 20.35 Synthesize each compound from...Ch. 20 - Prob. 20.36PCh. 20 - 20.37 Devise a synthesis of each alcohol from...Ch. 20 - 20.38 Draw the products formed when pentanal is...Ch. 20 - 20.39 Draw the product formed when is treated...Ch. 20 - The stereochemistry of the products of reduction...Ch. 20 - Prob. 20.41PCh. 20 - 20.42 Draw the products or each reduction...Ch. 20 - Prob. 20.43PCh. 20 - 20.44 Draw all stereoisomers formed in each...Ch. 20 - Prob. 20.45PCh. 20 - 20.46 Treatment of ketone A with ethynylithium...Ch. 20 - 20.47 Explain why metal hydride reduction gives an...Ch. 20 - Prob. 20.48PCh. 20 - 20.49 Identify the lettered compounds in the...Ch. 20 - Prob. 20.50PCh. 20 - 20.51 Draw a stepwise mechanism for the following...Ch. 20 - 20.52 Draw a stepwise mechanism for the following...Ch. 20 - Prob. 20.53PCh. 20 - 20.54 Draw a stepwise mechanism for the following...Ch. 20 - Prob. 20.55PCh. 20 - Prob. 20.56PCh. 20 - 20.57 What ester and Grignard reagent are needed...Ch. 20 - 20.58 What organolithium reagent and carbonyl...Ch. 20 - 20.59 What epoxide and organometallic reagent are...Ch. 20 - Prob. 20.60PCh. 20 - 20.61 Propose two different methods to synthesize...Ch. 20 - 20.62 Synthesize each compound from cyclohexanol...Ch. 20 - 20.63 Convert propan-2-ol into each compound....Ch. 20 - 20.64 Convert benzene into each compound. You may...Ch. 20 - 20.65 Design a synthesis of each compound from...Ch. 20 - 20.66 Synthesize each compound from the given...Ch. 20 - Prob. 20.67PCh. 20 - Prob. 20.68PCh. 20 - 20.69 An unknown compound A (molecular formula )...Ch. 20 - 20.70 Treatment of compound C (molecular formula )...Ch. 20 - 20.71 Treatment of compound E (molecular formula )...Ch. 20 - 20.72 Reaction of butanenitrile () with methyl...Ch. 20 - 20.73 Treatment of isobutene with forms a...Ch. 20 - 20.74 Draw a stepwise mechanism for the following...Ch. 20 - Prob. 20.75PCh. 20 - 20.76 Lithium tri-sec-butylborohydride, also known...Ch. 20 - Prob. 20.77PCh. 20 - Prob. 20.78PCh. 20 - Prob. 20.79PCh. 20 - 20.80 Draw a stepwise mechanism for the following...Ch. 20 - Prob. 20.81P
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