Ochem problem

[allstardentist]

The reaction of 2-chloro-2- methylhexane with sodium cyanide in ethanol results in

a. the retention of absolute config.
b. the formation of a racemic mixture
c. .....
d. ...
e. the formation of optically inactive products.

It seems like the reactant will go through SN1 reaction by the info. given. Doesn't that mean the answer will be either B or E? I put B and the solution is E. Can anyone explain? Thanks

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[allstardentist]

oh nm.. the reactant doesnt have any stereocenter.im stupid

 

[keibee82]

The reaction of 2-chloro-2- methylhexane with sodium cyanide in ethanol results in

a. the retention of absolute config.
b. the formation of a racemic mixture
c. .....
d. ...
e. the formation of optically inactive products.

It seems like the reactant will go through SN1 reaction by the info. given. Doesn't that mean the answer will be either B or E? I put B and the solution is E. Can anyone explain? Thanks

This will go E2 reaction. CN- is strong nucleophile(base) but substrate is tertiary Sn2 is not possible.
Therefore only choice is E2 and since the product of E2 will be alkene, its optically inactive.