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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(1λ5-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(1λ5-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 p-toluidine can be converted to the following compounds, using any necessary reagents.

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

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

a) Guanidine (shown) is about as strong base as hydroxide ion. Explain why guanidine is a much stronger base than most other amines.

(b) Show why p-nitroaniline is a much weaker base (3 pKb units weaker) than aniline.

(c) Explain why N,N-2,6-tetramethylaniline (shown) is a much stronger base than N,N-dimethylaniline.

Show how to synthesize the following amines from the indicated starting materials by acylation–reduction.

(a) N-butylpiperidine from piperidine

(b) N-benzylaniline from anilinea
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