Question: The two seemingly similar reactions shown below differ in their outcomes. The first proceeds in high yield. The yield of the product in the second,

The two seemingly similar reactions shown below differ in their outcomes.

The first proceeds in high yield. The yield of the product in the second, however, is diminished by the formation of (CH3CH2CH2CH2)2 S in substantial quantities. Discuss the formation of this by-product mechanistically, and explain why it occurs in the second case but not in the first.

CH,CH CHCH2Br NaOH, CH,CH OH, CH CH,CH,CH OH CH CH CH2CH2OH CH,CH,CH,CH,Br NaSH. CHCH,OH CH:CH2CH CH SH

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