Answer to Question #209955 in Organic Chemistry for mlindi

Question

Which of the following reactions is INCORRECT as indicated by the mechanism of the reaction and the major product formed in the reaction? (1) Via the SN1 reaction mechanism:  (2) Via the SN2 reaction mechanism:  (3) Via the SN2 reaction mechanism: CH3CH2CH2CH2CH2OH  +  HCl → CH3CH2CH2CH2CH2Cl +  H2O  (4) Via the SN2 reaction mechanism: CH3CH2OH+HBrCH3CH2Br+H2O 

Answer 1

(1) Via the SN1 reaction mechanism

Tertiary alcohol do not participate in SN2 reactions because of steric hindrance. Tertiary structures can form highly stable cations by simple loss of the leaving group therefore secondary and tertiary alcohols undergo SN1 reactions, while primary alcohol undergo SN2 reaction. Primary alcohols cannot undergo SN1 reactions because primary carbocations are too unstable to be formed. Therefore, when a primary alcohol reacts with a hydrogen halide, it must do so in an SN2 reaction.

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