객관식
Which energy diagram best represents an reaction?
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7. Substitution Reactions
SN2 Reaction
객관식
Why is 2-bromo-2-methylpropane unable to undergo an reaction?
A
The molecule is too polar for an mechanism to occur.
B
The reaction requires a carbocation intermediate, which cannot form in this case.
C
The bromine atom is not a good leaving group in this molecule.
D
The central carbon is too sterically hindered for the nucleophile to attack in a backside manner.
검증된 단계별 안내1
Understand that an SN2 reaction involves a nucleophile attacking the electrophilic carbon from the backside, leading to a single-step displacement of the leaving group.
Identify the structure of 2-bromo-2-methylpropane: it is a tertiary alkyl halide where the central carbon is bonded to three methyl groups and one bromine atom.
Recognize that the bulky methyl groups around the central carbon create significant steric hindrance, which physically blocks the nucleophile from accessing the backside of the carbon atom.
Recall that steric hindrance is a key factor that slows down or prevents SN2 reactions because the nucleophile cannot effectively approach the electrophilic center to perform the backside attack.
Conclude that due to this steric hindrance, 2-bromo-2-methylpropane cannot undergo an SN2 mechanism, and instead, it typically reacts via an SN1 mechanism where the carbocation intermediate is formed.
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