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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

Question: Predict the products of the following reactions:

(a)

(b)

(c)

Question:The trimethylsilyl (TMS) protecting group is one of several silicon protecting groups for alcohols. For each reaction, draw the mechanism for the protection of (R)-3-bromo-1-butanol with the following silyl chlorides, using triethylamine as the base:

(a) tert-butyldimethylsilyl chloride (TBS-Cl)

(b) triisopropylsilyl chloride (TIPS-Cl)

(c) triethylsilyl chloride (TES-Cl)

The trimethylsilyl (TMS) protecting group is one of several silicon protecting groups for alcohols. For each reaction, draw the mechanism for the protection of (R)-3-bromo-1-butanol with the following silyl chlorides, using triethylamine as the base:

(a) tert-butyldimethylsilyl chloride (TBS-Cl)

(b) triisopropylsilyl chloride (TIPS-Cl)

(c) triethylsilyl chloride (TES-Cl)

Question:Acid-catalyzed dehydration of 2,2-dimethylcyclohexanol yields a mixture of 1,2-methylcyclohexane and isopropylidenecyclopentane. Propose a mechanism to account for the formation of both products.

What alcohols would give the following products on oxidation?

(a)

(b)

(c)
See all solutions

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