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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

A compound of formula C11H16N2gives the IR, 1HNMR, and 13CNMR spectra shown. The proton NMR peak at未 2.0disappears on shaking with D2O. Propose a structure for this compound, and show how your structure accounts for the observed absorptions.

Rank the amines in each set in order of increasing basicity.

Predict the products from the reactions of the following amines with sodium nitrite in dilute.

  1. Cyclohexanamine
  2. N-ethylhexan-2-amine
  3. Piperidine
  4. Aniline

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.

When the (R,R) isomer of the amine shown is treated with an excess of methyl iodide, then silver oxide, then heated, the major product is the Hofman product.

  1. Draw the structure of the major (Hofman) product.
  2. Some Zaitsev product is also formed. It has the (E) configuration. When the same amine is treated with m-CPBA and heated, the Zaitsev product has the (Z) configuration. Use stereochemical drawings of the transition states to explain these observations.
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