Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 20, Problem 20.44P

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

a. ( CH 3 ) 2 CHCH 2 CH 2 CHO c. ( CH 3 ) 2 CHCH 2 CH 2 C ( OH ) ( C 6 H 5 ) 2

b. ( CH 3 ) 2 CHCH 2 CH 2 COCH = CH 2 d. ( CH 3 ) 2 CHCH 2 CH 2 CH 2 OH

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation:

The reagent needed to convert (CH3)2CHCH2CH2COCl to given compound is to be predicted.

Concept introduction:

Acid chlorides, which contains good leaving group Cl, on reaction with organometallic compounds give ketone or alcohol as a product. Alkyl group from organometallic compound occupies the position of leaving group Cl.

Answer to Problem 20.44P

The reagent needed to convert (CH3)2CHCH2CH2COCl 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 20.44P , additional homework tip  1

Figure 1

Therefore, LiAl(OBu)3H is needed to convert (CH3)2CHCH2CH2COCl to given compound.

Conclusion

The reagent needed to convert (CH3)2CHCH2CH2COCl to given compound is LiAl(OBu)3H.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation:

The reagent needed to convert (CH3)2CHCH2CH2COCl to given compound is to be predicted.

Concept introduction:

Acid chlorides, which contains good leaving group Cl, on reaction with organometallic compounds give ketone or alcohol as a product. Alkyl group from organometallic compound occupies the position of leaving group Cl.

Answer to Problem 20.44P

The reagent needed to convert (CH3)2CHCH2CH2COCl to given compound is (H2C=CH)2CuLi.

Explanation of Solution

The structure of given ketone compound shows that one ethene molecule is attached to carbonyl carbon. Acid chlorides on reaction with one equivalent of organocuprate reagent convert into ketone. The organocuprate reagent removes the good leaving Cl atom and leads to the formation of ketone. The conversion of (CH3)2CHCH2CH2COCl to given compound by the use of (H2C=CH)2CuLi is shown in Figure 2.

Organic Chemistry, Chapter 20, Problem 20.44P , additional homework tip  2

Figure 2

Therefore, (H2C=CH)2CuLi is needed to convert (CH3)2CHCH2CH2COCl to given compound.

Conclusion

The reagent needed to convert (CH3)2CHCH2CH2COCl to given compound is (H2C=CH)2CuLi.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation:

The reagent needed to convert (CH3)2CHCH2CH2COCl to given compound is to be predicted.

Concept introduction:

Acid chlorides, which contains good leaving group Cl, on reaction with organometallic compounds give ketone or alcohol as a product. Alkyl group from organometallic compound occupies the position of leaving group Cl.

Answer to Problem 20.44P

The reagent needed to convert (CH3)2CHCH2CH2COCl to given compound is C6H5MgBr.

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)2CHCH2CH2COCl to given compound by the use of two equivalents of C6H5MgBr is shown in Figure 3.

Organic Chemistry, Chapter 20, Problem 20.44P , additional homework tip  3

Figure 3

Therefore, C6H5MgBr is needed to convert (CH3)2CHCH2CH2COCl to given compound.

Conclusion

The reagent needed to convert (CH3)2CHCH2CH2COCl to given compound is C6H5MgBr.

Expert Solution
Check Mark
Interpretation Introduction

(d)

Interpretation:

The reagent needed to convert (CH3)2CHCH2CH2COCl to given compound is to be predicted.

Concept introduction:

Acid chlorides, which contains good leaving group Cl, on reaction with organometallic compounds give ketone or alcohol as a product. Alkyl group from organometallic compound occupies the position of leaving group Cl.

Answer to Problem 20.44P

The reagent needed to convert (CH3)2CHCH2CH2COCl 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 20.44P , additional homework tip  4

Figure 4

Therefore, LiAlH4 is needed to convert (CH3)2CHCH2CH2COCl to given compound.

Conclusion

The reagent needed to convert (CH3)2CHCH2CH2COCl to given compound is LiAlH4.

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Chapter 20 Solutions

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