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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.

Question. Which of the amines listed next is resolved into enantiomers? In each case, explain why interconversion of the enantiomers does or does not take place.

  1. Cis-2-methylcyclohexanamine
  2. N-ethyl-N-methylcyclohexanamine
  3. N-methylaziridine
  4. Ethylmethylanilinium iodide
  5. Methylethylpropylisopropylammonium iodide

The proton and 13C NMR spectra of a compound of formula C4H11N are shown here. Determine the structure of this amine, and give peak assignments for all of the protons in the structure.

Predict the products of the following reactions:

(a) excessโ€‰โ€‰NH3โ€‰โ€‰+โ€‰โ€‰Phโˆ’CH2CH2CH2Brโ†’

(b)1โˆ’bromopentaneโ†’(2)LiAlH4(3)H3O+(1)NaN3

(c)

(d) productโ€‰โ€‰fromโ€‰โ€‰partโ€‰โ€‰cโ†’heat

(e)

(f) productโ€‰โ€‰fromโ€‰โ€‰partโ€‰โ€‰eโ†’(3)heat(1)excessCH3I(2)Ag2O

(g)

(h)

(i)

(j) productโ€‰โ€‰fromโ€‰โ€‰partโ€‰โ€‰iโ†’(2)H3O+(1)LiAlH4

(k)

(l)

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

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