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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

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 the substituents containing the azo group () can facilitate both electrophilic and nucleophilic aromatic substitution.

A.Hafner and S.Brase, Angewandte Chemie Int. Ed., M.Heinrich et al., Journal of Organic Chemistry, 2012, 77, 1520. 2012, 51, 3713

Question. (a) Propose a mechanism for the reaction of 2-bromopyridine with sodium amide to give 2-aminopyridine.

(b) When 3-bromopyridine is used in this reaction, stronger reaction conditions are required and a mixture of 3-aminopyridine and 4-aminopyridine results. Propose a mechanism to explain this curious result.

Question. The carbon NMR chemical shifts of diethylmethylamine, piperidine, propan-1-ol, and propanal follow. Determine which spectrum corresponds to each structure, and show which carbon atom(s) are responsible for each absorption.

(a) 25.9, 27.8, 47.9

(b) 12.4, 41.0, 51.1

(c) 7.9, 44.7, 201.9

(d) 10.0, 25.8, 63.6

Propose a mechanism for the synthesis of methyl orange.
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