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Chapter 22: 6P (page 868)

Why can鈥檛 1-methylcyclohexanol be prepared from a carbonyl compound by reduction?

Short Answer

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Answer

In 1-methyl cyclohexanol, tertiary alcohol is present, hence it can鈥檛 be reduced from any carbonyl compound.

Step by step solution

01

Step-by-Step Solution Step 1: Function of metal hydrides

Metal hydrides such as sodium borohydride and lithium aluminium hydride are strong reducing agents that can reduce an aldehyde into primary alcohol and a ketone into secondary alcohol.

These are as shown below:

02

Structure of 1-methylcyclohexanol

The structure of 1-methylcyclohexanol has a tertiary alcoholic group, which is shown below:

03

Observation of the structure

The structure contains a tertiary alcohol group where no 伪-hydrogen is present. Hence, it cannot be reduced by any carbonyl group, as the valency of the carbonyl group exceeds its valency of 4.

Based on the explanations, in the case of 1-methyl cyclohexanol, tertiary alcohol is present. Hence, it can鈥檛 be reduced from any carbonyl compound.

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Most popular questions from this chapter

Question: Explain why imidazolides are much more reactive than other amides in nucleophilic acyl substitution.

Question:Outline two different ways that butan-2-one can be prepared from a nitrile and a Grignard reagent.

What Grignard reagent and aldehyde (or ketone) are needed to prepare each alcohol? Show all possible routes

(a)

(b)

(c)

Question: Explain why CH3CONH2 is a stronger acid and a weaker base than CH3CH2NH2 .

Question: Give the structure corresponding to each name.

  1. cyclohexyl propanoate
  2. cyclohexanecarboxamide
  3. 4-methylheptanenitrile
  4. vinyl acetate
  5. benzoic propanoic anhydride
  6. 3-methylhexanoyl chloride
  7. octyl butanoate
  8. N,N-dibenzylformamide
See all solutions

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