Orgo Reaction Question

[Rach7]

The reactions of CH3CHICH2CH3 with aqueous sodium hydroxide gives a mixture of products. This is because

A) The only reaction, SN2, produces a racemic mixture of alcohols.
B) SN1 and SN2 reactions produce a racemic mixture of alcohols, while 1-butene, the major component of the alkenes, is the result of an E2 reaction.
C) An E1 reaction produces a racemic mixture of alcohols, while an E2 reaction produces a mixture of alkenes.
D) The carbocation intermediate of SN1 and E1 reactions undergoes rearrangement, producing alkenes and a racemic mixture of alcohols.
E) The product mixture contains alcohols and alkenes, all the result of SN1, SN2, E1, and E2.

Kaplan says the answer is E. It goes on to say that since NaOH is a good nucleophile and a strong base, SN2 and E2 are favored. So why does the answer include E1 and SN1?

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[wantVCUdental]

The reactions of CH3CHICH2CH3 with aqueous sodium hydroxide gives a mixture of products. This is because

A) The only reaction, SN2, produces a racemic mixture of alcohols.
B) SN1 and SN2 reactions produce a racemic mixture of alcohols, while 1-butene, the major component of the alkenes, is the result of an E2 reaction.
C) An E1 reaction produces a racemic mixture of alcohols, while an E2 reaction produces a mixture of alkenes.
D) The carbocation intermediate of SN1 and E1 reactions undergoes rearrangement, producing alkenes and a racemic mixture of alcohols.
E) The product mixture contains alcohols and alkenes, all the result of SN1, SN2, E1, and E2.

Kaplan says the answer is E. It goes on to say that since NaOH is a good nucleophile and a strong base, SN2 and E2 are favored. So why does the answer include E1 and SN1?

Iodide is a huge halogen, because it has so many protons, it is able to stabilize a negative charge much better than say a Flouride. This property makes Iodide and extremely good leaving group, so this reaction proceeds in the order of Iodide leaving first to form a secondary carbocation (moderately stable). And then the OH- base can extract a hydrogen or just attack the not very hindered carbocation.

Since the leaving group goes first, this is an E1/Sn1 process 😛

 

[Rach7]

Thank you for your reply!