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Chapter 19: Q46P (page 1031)

Propose mechanisms for the following reactions.

Short Answer

Expert verified

At first the cyclohexanone is converted tocyclohexylidene(1位5-ethyl)ammonium. Then thiscompound is reduced to the main desired product. Here the sodium triacetoxyborhydride is used as the reducing agent as sodium borohydrate.

Step by step solution

01

Reduction using Sodiumtriacetoxyborohydride

At first the cyclohexanone is converted tocyclohexylidene(1位5-ethyl)ammonium. Then thiscompound is reduced to the main desired product. Here the sodium triacetoxyborhydride is used as the reducing agent as sodium borohydrate.

02

:Elimination then reduction

The keto group is converted to hydroxyl group in presence of acid. Then elimination occurs and alkene is formed. This alkene is reduced in presence of H2/platinum in acidic medium.

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Most popular questions from this chapter

Show how you would convert aniline to the following compounds

(a)flurobenzene (b) chlorobenzene

(c) 1,3,5- trimethylbenzene(d) bromobenzene

(e) iodobenzene(f) benzonitrile

(g) phenol

(h)

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

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.

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

Show how you would use the same sulfonyl chloride as used in the sulfanilamide synthesis to make sulfathiazole and sulfapyridine.
See all solutions

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