Which of the following is not a good method for the synthesis of 1-chlorohexane:

Question

Which of the following is not a good method for the synthesis of 1-chlorohexane:

A. 1-hexanol + HCl

B. 1-hexanol + TsCl and Et3N to make a 1-hexyl tosylate, followed by an SN2 reaction with NaCl

C. 1-hexanol + thionyl chloride

D. 1-hexanol + HCl with ZnCl2 as a catalyst

The Pinacol rearrangment involves the reaction of a/an _________ with H2SO4 to give a/an ________, and the reaction proceeds through a ____________ intermediate.

A. alkene; ketone; carbocation

B. vicinal diol; ketone; carbocation

C. vicinal diol; aldehyde; carbocation

D. vicinal diol; ketone; radical

E. vicinal diol; alkene; carbocation

A. alkene; ketone; carbocation

B. vicinal diol; ketone; carbocation

C. vicinal diol; aldehyde; carbocation

D. vicinal diol; ketone; radical

E. vicinal diol; alkene; carbocation

Explanation / Answer

Which of the following is not a good method for the synthesis of 1-chlorohexane:

B. 1-hexanol + TsCl and Et3N to make a 1-hexyl tosylate, followed by an SN2 reaction with NaCl

It can give 1-hexene as side product by 1,2 elimination of TfOH

The Pinacol rearrangment involves the reaction of a vicinal diol with H2SO4 to give ketone, and the reaction proceeds through a carbocation intermediate.

B. vicinal diol; ketone; carbocation

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