Starting from 1-hexene, what is the product of the following reactions?1. Br2, CCl4 2. xs NaNH2, then H2O 3. NaH 4. BrCH2CH2CH3Select answer from the options below2-heptyne3-nonyne2-bromo-2-hexane4-nonyne1-hexyne
Question
Starting from 1-hexene, what is the product of the following reactions?1. Br2, CCl4 2. xs NaNH2, then H2O 3. NaH 4. BrCH2CH2CH3Select answer from the options below2-heptyne3-nonyne2-bromo-2-hexane4-nonyne1-hexyne
Solution
The product of the following reactions starting from 1-hexene would be 3-nonyne. Here's the step-by-step process:
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The reaction of 1-hexene with Br2 in CCl4 will result in an anti-addition of Br atoms due to the formation of a bromonium ion intermediate. This will give you 1,2-dibromohexane.
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Excess NaNH2 will remove both bromine atoms in two separate E2 elimination reactions, resulting in a triple bond formation. This will give you 1-hexyne.
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NaH is a strong base and will deprotonate the terminal alkyne, forming a nucleophilic acetylide ion.
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The acetylide ion will then perform an SN2 reaction on BrCH2CH2CH3, adding a three-carbon chain to the molecule. This will give you 3-nonyne.
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