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Chapter 17: Q50P (page 567)

What products would you expect to obtain from reaction of 1-methylcyclohexanol with the following reagents?

(a) HBr (b) NaH (c) H2SO4 (d) Na2Cr2O7

Short Answer

Expert verified

The treatment of an alcohol with HBr leads to the formation of alkyl bromide. The reaction of alcohols with NaH yields alkoxide. The reaction of alcohols with sulphuric acid leads to the formation of alkenes. Tertiary alcohols do not undergo any reaction when reacted with Na2Cr2O7.

Step by step solution

01

Reaction of alcohols with several reagents

The treatment of an alcohol with HBr leads to the formation of alkyl bromide. The reaction of alcohols with NaH yields alkoxide. The reaction of alcohols with sulphuric acid leads to the formation of alkenes. Tertiary alcohols do not undergo any reaction when reacted with Na2Cr2O7.

02

Reaction of 1-methylcyclohexanol with several reagents

(a) 1-methylcyclohexanol reacts with HBr to produce 1-bromo-1-methylcyclopentane. The reaction can be given as:

(b) 1-methylcyclohexanol reacts with NaH to form sodium-1-methylcyclopentanolate. The reaction can be given as:

(c) 1-methylcyclohexanol reacts with to form 1-methylcylochex-1-ene. The reaction can be given as:

(d) 1-methylcyclohexanol does not react with Na2Cr2O7 as tertiary alcohols are not oxidized by Na2Cr2O7.

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Most popular questions from this chapter

What carbonyl compounds might you start with to prepare the following compounds by Grignard reaction? List all possibilities.

(a) 2-Methyl-2-propanol

(b) 1-Ethylcyclohexanol

(c) 3-Phenyl-3-pentanol

(d) 2-Phenyl-2-pentanol

(e)

(f)

Treatment of the following epoxide with aqueous acid produces a carbocation intermediate that reacts with water to give a diol product. Show the structure of the carbocation, and propose a mechanism for the second step.

Use the reaction of a Grignard reagent with a carbonyl compound to synthesize the following compound:

Benzyl chloride can be converted intobenzaldehyde by treatment with nitromethane and base. The reactioninvolves the initial conversion of nitromethane in to its anion, followed by SN2 reaction of the anion with benzyl chloride and subsequent E2 reaction. Write the mechanism in detail, using curved arrows to indicate the electron flow in each step.

Benzyl chloride Nitromethane anion Benzaldehyde

How would you synthesize the following alcohols, starting with benzene and other alcohols of six or fewer carbons as your only organic reagents?

(a)

(b)

(c)

(d)
See all solutions

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