ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 20, Problem 20.30P

What reagent is needed to convert ( CH 3 ) 2 CHCH 2 COCl into each compound?

a. Chapter 20, Problem 20.30P, Problem 20.30 What reagent is needed to convert  into each compound?
a. 	b. 	c. 	d. 
 , example  1 b. Chapter 20, Problem 20.30P, Problem 20.30 What reagent is needed to convert  into each compound?
a. 	b. 	c. 	d. 
 , example  2 c. Chapter 20, Problem 20.30P, Problem 20.30 What reagent is needed to convert  into each compound?
a. 	b. 	c. 	d. 
 , example  3 d. Chapter 20, Problem 20.30P, Problem 20.30 What reagent is needed to convert  into each compound?
a. 	b. 	c. 	d. 
 , example  4

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation: The reagent needed to convert (CH3)2CHCH2COCl to given compound is to be predicted.

Concept introduction: Acid chlorides, which contains good leaving group Cl, on reaction with organocuprate give ketone as a product. Alkyl group from organocuprate occupies the position of leaving group Cl.

Answer to Problem 20.30P

The reagent needed to convert (CH3)2CHCH2COCl to given compound is LiAl(OBu)3H.

Explanation of Solution

The given compound is aldehyde. Acid chlorides on reaction with mild reducing agent like lithium tri-tert-butoxyaluminium hydride (LiAl(OBu)3H) converts into aldehyde as shown in Figure 1.

ORGANIC CHEMISTRY, Chapter 20, Problem 20.30P , additional homework tip  1

Figure 1

Therefore, LiAl(OBu)3H is needed to convert (CH3)2CHCH2COCl to given compound.

Conclusion

The reagent needed to convert (CH3)2CHCH2COCl to given compound is LiAl(OBu)3H.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The reagent needed to convert (CH3)2CHCH2COCl to given compound is to be predicted.

Concept introduction: Acid chlorides, which contains good leaving group Cl, on reaction with organocuprate give ketone as a product. Alkyl group from organocuprate occupies the position of leaving group Cl.

Answer to Problem 20.30P

The reagent needed to convert (CH3)2CHCH2COCl to given compound is CH3CH2MgBr.

Explanation of Solution

The structure of given ketone compound shows that the hydroxyl group is attached to tertiary carbon atom. Acid chlorides on reaction with two equivalents of Grignard reagent convert into tertiary alcohol. The first equivalent of Grignard reagent remove good leaving Cl group and second equivalent converts ketone to alcohol. The conversion of (CH3)2CHCH2COCl to given compound by the use of CH3CH2MgBr is shown in Figure 2.

ORGANIC CHEMISTRY, Chapter 20, Problem 20.30P , additional homework tip  2

Figure 2

Therefore, CH3CH2MgBr is needed to convert (CH3)2CHCH2COCl to given compound.

Conclusion

The reagent needed to convert (CH3)2CHCH2COCl to given compound is CH3CH2MgBr.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The reagent needed to convert (CH3)2CHCH2COCl to given compound is to be predicted.

Concept introduction: Acid chlorides, which contains good leaving group Cl, on reaction with organocuprate give ketone as a product. Alkyl group from organocuprate occupies the position of leaving group Cl.

Answer to Problem 20.30P

The reagent needed to convert (CH3)2CHCH2COCl to given compound is (CH3CH2)2CuLi.

Explanation of Solution

The structure of given compound shows that the carbonyl carbon is attached to ethyl group. Ethyl group can occupy the position of leaving group Cl when (CH3)2CHCH2COCl is treated with (CH3CH2)2CuLi as shown in Figure 3.

ORGANIC CHEMISTRY, Chapter 20, Problem 20.30P , additional homework tip  3

Figure 3

Therefore, (CH3CH2)2CuLi is needed to convert (CH3)2CHCH2COCl to given compound.

Conclusion

The reagent needed to convert (CH3)2CHCH2COCl to given compound is (CH3CH2)2CuLi.

Expert Solution
Check Mark
Interpretation Introduction

(d)

Interpretation: The reagent needed to convert (CH3)2CHCH2COCl to given compound is to be predicted.

Concept introduction: Acid chlorides, which contains good leaving group Cl, on reaction with organocuprate give ketone as a product. Alkyl group from organocuprate occupies the position of leaving group Cl.

Answer to Problem 20.30P

The reagent needed to convert (CH3)2CHCH2COCl to given compound is LiAlH4.

Explanation of Solution

Acid chlorides on reaction with strong reducing agent like lithium aluminium hydride (LiAlH4) converts into primary alcohol as shown in Figure 4.

ORGANIC CHEMISTRY, Chapter 20, Problem 20.30P , additional homework tip  4

Figure 4

Therefore, LiAlH4 is needed to convert (CH3)2CHCH2COCl to given compound.

Conclusion

The reagent needed to convert (CH3)2CHCH2COCl to given compound is LiAlH4.

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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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