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Chapter 19: Q17P (page 1001)

Give the products expected from the following reactions:

(a) acetyl chloride + ethylamine

(b) benzoyl chloride +dimethylamine

(c) hexanoyl chloride + piperidine

Short Answer

Expert verified

(a)

(b)

(c)

Step by step solution

01

A concept:

Acetyl chloride + ethylamine : Combine to give N-ethylacetamide and hydrochloric acid.

Benzoyl chloride + dimethylamine: Combine to give N,N- dimethylbenzamide

Hexanoyl chloride + piperidine: Combine to give 1-(1-piperidyl)hexan-1-one

02

The products expected:

(a) acetyl chloride + ethylamine : Combine to give N-ethylacetamide and hydrochloric acid.


(b) benzoyl chloride + dimethylamine: Combine to give N,N- dimethylbenzamide.

(c) hexanoyl chloride + piperidine: Combine to give 1-(1-piperidyl)hexan-1-one.

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Most popular questions from this chapter

Show how p-toluidine can be converted to the following compounds, using any necessary reagents.

We have considered nucleophilic aromatic substitution of pyridine at the 2-position and 3-position but not the at the 4-position. Complete the three possible cases by showing the mechanism for the reaction of methoxide ion with 4-chloropyridine. Show how the intermediate is stabilized by delocalization of the charge onto the nitrogen atom.

Show how you would accomplish the following synthetic conversions.

(a) benzyl bromide to benzylamine

(b) 1-bromo-2-phenylethane to 3-phenylpropan-1-amine

(c) pentanoic acid to pentan-1-amine

(d) pentanoic acid to hexan-1-amine

(e) (R)-2-bromobutane to (S)-butan-2-amine

(f) (R)-2-bromobutane to (S)-2-methylbutan-1-amine

(g) hexan-2-one to 1-amino-2-methylhexan-2-ol

Within each structure, rank the indicated nitrogens by increasing basicity.

In Section 19-10B, we saw that pyridine undergoes electrophilic aromatic substitution reluctantly, requiring strong conditions and giving disappointing yields. In contrast, pyridine N-oxide undergoes EAS under moderate conditions, giving good yields of substitution on C2 and C4. Explain this surprising difference.
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