ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 20, Problem 20.36P
Interpretation Introduction

(a)

Interpretation: The products formed by the treatment of NaBH4,CH3OH with compound A and B are to be drawn.

Concept introduction: Organometallic reagents like RLi,RMgX and R2CuLi are the source of R, which acts as a nucleophile. Ketones on reaction with Grignard reagent converts into tertiary alcohol whereas aldehydes give primary and secondary alcohol.

Expert Solution
Check Mark

Answer to Problem 20.36P

The products formed by the treatment of NaBH4,CH3OH with compound A is,

ORGANIC CHEMISTRY, Chapter 20, Problem 20.36P , additional homework tip  1

Figure 1

Compound B do not react with NaBH4,CH3OH.

Explanation of Solution

The ball and stick model of compound A and B shows that black balls represent carbon atom, white balls represent hydrogen atom and red balls represent oxygen atom. Therefore, the structure of A and B is,

ORGANIC CHEMISTRY, Chapter 20, Problem 20.36P , additional homework tip  2

Figure 2

Ketones on reaction with NaBH4 form secondary alcohol however, esters do not reaction with NaBH4. Therefore, the products formed by the treatment of NaBH4,CH3OH with compound A is,

ORGANIC CHEMISTRY, Chapter 20, Problem 20.36P , additional homework tip  3

Figure 3

Conclusion

The products formed by the treatment of NaBH4,CH3OH with compound A is shown in Figure 3. Compound B do not reaction with NaBH4,CH3OH.

Interpretation Introduction

(b)

Interpretation: The products formed by the treatment of LiAlH4,H2O with compound A and B are to be drawn.

Concept introduction: Organometallic reagents like RLi,RMgX and R2CuLi are the source of R, which acts as a nucleophile. Ketones on reaction with Grignard reagent converts into tertiary alcohol whereas aldehydes give primary and secondary alcohol.

Expert Solution
Check Mark

Answer to Problem 20.36P

The products formed by the treatment of LiAlH4,H2O with compound A and B are,

ORGANIC CHEMISTRY, Chapter 20, Problem 20.36P , additional homework tip  4

Figure 4

Explanation of Solution

The structure of A and B is shown in Figure 2.

Ketones on reaction with LiAlH4 form secondary alcohol and esters form primary alcohol. Therefore, the products formed by the treatment of LiAlH4,H2O with compound A and B are,

ORGANIC CHEMISTRY, Chapter 20, Problem 20.36P , additional homework tip  5

Figure 5

Conclusion

The products formed by the treatment of LiAlH4,H2O with compound A and B are shown in Figure 5.

Interpretation Introduction

(c)

Interpretation: The products formed by the treatment of CH3MgBr,H2O with compound A and B are to be drawn.

Concept introduction: Organometallic reagents like RLi,RMgX and R2CuLi are the source of R, which acts as a nucleophile. Ketones on reaction with Grignard reagent converts into tertiary alcohol whereas aldehydes give primary and secondary alcohol.

Expert Solution
Check Mark

Answer to Problem 20.36P

The products formed by the treatment of CH3MgBr,H2O with compound A and B are,

ORGANIC CHEMISTRY, Chapter 20, Problem 20.36P , additional homework tip  6

Figure 6

Explanation of Solution

The structure of A and B is shown in Figure 2.

Ketones and esters on reaction with Grignard reagent form tertiary alcohol. Therefore, the products formed by the treatment of CH3MgBr,H2O with compound A and B are,

ORGANIC CHEMISTRY, Chapter 20, Problem 20.36P , additional homework tip  7

Figure 7

Conclusion

The products formed by the treatment of CH3MgBr,H2O with compound A and B are shown in Figure 7.

Interpretation Introduction

(d)

Interpretation: The products formed by the treatment of C6H5Li,H2O with compound A and B are to be drawn.

Concept introduction: Organometallic reagents like RLi,RMgX and R2CuLi are the source of R, which acts as a nucleophile. Ketones on reaction with Grignard reagent converts into tertiary alcohol whereas aldehydes give primary and secondary alcohol.

Expert Solution
Check Mark

Answer to Problem 20.36P

The products formed by the treatment of C6H5Li,H2O with compound A and B are,

ORGANIC CHEMISTRY, Chapter 20, Problem 20.36P , additional homework tip  8

Figure 8

Explanation of Solution

The structure of A and B is shown in Figure 2.

Ketones and esters on reaction with organolithium reagent form tertiary alcohol. Therefore, the products formed by the treatment of C6H5Li,H2O with compound A and B are,

ORGANIC CHEMISTRY, Chapter 20, Problem 20.36P , additional homework tip  9

Figure 9

Conclusion

The products formed by the treatment of C6H5Li,H2O with compound A and B are shown in Figure 9.

Interpretation Introduction

(e)

Interpretation: The products formed by the treatment of Na2Cr2O7,H2SO4,H2O with compound A and B are to be drawn.

Concept introduction: Organometallic reagents like RLi,RMgX and R2CuLi are the source of R, which acts as a nucleophile. Ketones on reaction with Grignard reagent converts into tertiary alcohol whereas aldehydes give primary and secondary alcohol.

Expert Solution
Check Mark

Answer to Problem 20.36P

Compound A and B do not reaction with Na2Cr2O7,H2SO4,H2O. Hence, no product is formed.

Explanation of Solution

The structure of A and B is shown in Figure 2.

Ketones and esters do not undergo oxidation reaction with Na2Cr2O7,H2SO4,H2O. Therefore, no product is formed by the treatment of Na2Cr2O7,H2SO4,H2O with compound A and B.

Conclusion

Compound A and B do not reaction with Na2Cr2O7,H2SO4,H2O. Hence, no product is formed.

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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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