QuestionStarting from 1-hexene, what is the product of the following reactions?
1. $\mathrm{Br}_{2}, \mathrm{CCl}_{4}$ 2.xs $\mathrm{NaNH}_{2}$ , then $\mathrm{H}_{2} \mathrm{O}$ 3. NaH 4 . $\mathrm{BrCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}$ 2-heptyne 1-hexyne 4-nonyne 3-nonyne 2-bromo-2-hexane

Studdy Solution

STEP 1

1. The starting compound is 1-hexene.
2. The reactions are performed sequentially as listed.
3. Each reaction proceeds to completion under typical conditions.

STEP 2

1. Perform the first reaction: Addition of bromine to 1-hexene.
2. Perform the second reaction: Double dehydrohalogenation with excess sodium amide and water.
3. Perform the third reaction: Deprotonation with sodium hydride.
4. Perform the fourth reaction: Alkylation with 1-bromopropane.

STEP 3

Perform the first reaction: Addition of bromine to 1-hexene.
- 1-hexene reacts with $\mathrm{Br}_{2}$ in $\mathrm{CCl}_{4}$ to form 1,2-dibromohexane.

STEP 4

Perform the second reaction: Double dehydrohalogenation with excess sodium amide and water.
- 1,2-dibromohexane reacts with excess $\mathrm{NaNH}_{2}$ , followed by $\mathrm{H}_{2}\mathrm{O}$ , to form 1-hexyne.

STEP 5

Perform the third reaction: Deprotonation with sodium

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