Q50P - Organic Chemistry (Mcmurry)

Question

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

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

Step-by-Step Solution

Answer

Step 1: 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.

Step 2: 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.