TBR SN2, SN1, E2 stuff

[LoLCareerGoals]

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What difficulty arises if Reaction:

Nuc + CH3-X -> Nuc-CH3 + X

is carried out using a sec-propyl el-phil instead of the methyl el-phil?

A. The el-phil exhibits more steric hindrance.
B. The el-phil exhibits less steric hindrance.
C . There is the chance of an elimination side reaction.
D . The chance for an elimination side reaction is reduced.

Both A&C look fine to me. Book says C because A "is not a difficulty". Like hell it isn't what about SN1 competition kicking as a result of extra hindrance?
The whole reason leaving groups leaving "by themselves" in SN1 is because hindered el-phil pushes them off (according to the same book).
What am I missing?

 

[Captain Sisko]

What difficulty arises if Reaction:

Nuc + CH3-X -> Nuc-CH3 + X

is carried out using a sec-propyl el-phil instead of the methyl el-phil?

A. The el-phil exhibits more steric hindrance.
B. The el-phil exhibits less steric hindrance.
C . There is the chance of an elimination side reaction.
D . The chance for an elimination side reaction is reduced.

Both A&C look fine to me. Book says C because A "is not a difficulty". Like hell it isn't what about SN1 competition kicking as a result of extra hindrance?
The whole reason leaving groups leaving "by themselves" in SN1 is because hindered el-phil pushes them off (according to the same book).
What am I missing?

lol technically the difficulty is that you're using the wrong ephile to get that product. no way you're going to get MeNu if you use isopropyl! but if it's talking about the type of reaction I can see what they mean. 2ndary alkyl halide is going to have some elimination side reaction. as far as sn1 goes you could have some of that but the fact that you've a racemic mixture for product is irrelevant because it's not at a chiral carbon. am i making sense?

 

[LoLCareerGoals]

The passage describes an experiment that tries to figure out how good 4 different nucphils are and how good 4 different leaving groups are.
Pretty sure having some sn1 (where "some" cannot be quantified and thus "subtracted away") is going to f up your reaction rate measurements which is what's used to determine the goodness of these nucs/leaving groups. If it sucks up some of the nuc from the desired sn2, isn't that what is scientifically defined as "difficulty"?