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Chapter 25: PROBLEM 25.24 (page 1023)

Question: Draw the products formed when each carbonyl compound reacts with the following amines:

1. CH3CH2CH2NH2

2.(CH3CH2)2NH

a.

b.

c.

Short Answer

Expert verified

Answer

a.

b.

c.

Step by step solution

01

Reaction of carbonyl compounds and the amines

The carbonyl compounds act as an electrophile in the presence of a Lewis base. The amines are the Lewis base because they contain lone pairs of electrons.

An amine gives its electron to the carbonyl group and forms a bond on the place of either the leaving group or the carbonyl oxygen.

02

Explanation

a. The reactions of hexanone with the given amine compounds CH3CH2CH2NH2and (CH3CH2)2NH are shown as:

Reactions of hexanone with CH3CH2CH2NH2and (CH3CH2)2NH

b.The reactions of anhydride with the given amine compounds and are shown as:

Reactions of anhydride withCH3CH2CH2NH2and (CH3CH2)2NH

c. The reactions of acyl chloride with the given amine compounds and are shown as:

Reactions of acyl chloride withCH3CH2CH2NH2and (CH3CH2)2NH

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Most popular questions from this chapter

Question: Identify the intermediates (A鈥揅) in the following reaction sequence, which was used to prepare racemic ofloxacin. One enantiomer of the product, levofloxacin, is an antibiotic used to treat severe bacterial infections that have not responded to other drugs.

Rank the following compounds in order of increasing basicity and explain the order you choose.

Draw a stepwise mechanism for each reaction.

Question: Which amines cannot be prepared by a Gabriel synthesis? Explain your choices.

a.

b.

c.

d.

Treatment of compound D with LiAlH4 followed by H2O forms compound E. D shows a molecular ion in its mass spectrum at m/z= 71 and IR absorptions at 3600-3200cm-1 and . E shows a molecular ion in its mass spectrum at m/z= 75 and IR absorptions at 3636cm-1 and 3600-3200cm-1 . Propose structures for D and E from these data and the given 1H NMR spectra.
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