A student attempted the following reaction. What was the result and why? + ОН NaCI NaOH + Isolated an approximately 1:1 mixture of the original alcohol and the desired alkyl chloride, because chloride and hydroxide behave similarly as leaving groups. Isolated only the original alcohol, because hydroxide is a weaker base than chloride. Isolated the desired alkyl chloride, because hydroxide is a better leaving group than chloride. Isolated only the original alcohol, because hydroxide is a poorer leaving group than chloride. Isolated the desired alkyl chloride, because chloride is a better nucleophile than hydroxide.

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Chapter1: Chemical Foundations
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A student attempted the following reaction. What was the result and why?
+ NaCI
+ NaOH
HO
O Isolated an approximately 1:1 mixture of the original alcohol and the desired alkyl chloride, because chloride
and hydroxide behave similarly as leaving groups.
Isolated only the original alcohol, because hydroxide is a weaker base than chloride.
O Isolated the desired alkyl chloride, because hydroxide is a better leaving group than chloride.
O Isolated only the original alcohol, because hydroxide is a poorer leaving group than chloride.
Isolated the desired alkyl chloride, because chloride is a better nucleophile than hydroxide.
Transcribed Image Text:A student attempted the following reaction. What was the result and why? + NaCI + NaOH HO O Isolated an approximately 1:1 mixture of the original alcohol and the desired alkyl chloride, because chloride and hydroxide behave similarly as leaving groups. Isolated only the original alcohol, because hydroxide is a weaker base than chloride. O Isolated the desired alkyl chloride, because hydroxide is a better leaving group than chloride. O Isolated only the original alcohol, because hydroxide is a poorer leaving group than chloride. Isolated the desired alkyl chloride, because chloride is a better nucleophile than hydroxide.
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