[Morgrothiel]

I dunno if this is the right place to post this, but I think so

I have this task in my book, and I don't know how to solve it:

Which one of these bromides can be expected to give the largest amount of substitution products when reacting with NaOH

The bromides:


I could really need an explanation

Thank you for all your help

[english]

It definitely wouldn't be (c) because that is an aryl bromide (I'm assuming that is a bromide that is being cut off). 

Aryl halides have more electron density around the alpha carbon, that is, the electrophilic portion of the molecule to be substituted.


Is this an S_N1 or S_N2 reaction? 

You were given this information, right?

[Morgrothiel]

I didnt get more information than I gave you. And accordig to the answer sheet the answer is supposed to be d?

[english]

Well your base is strong, so that follows S_N2 conditions.

The nucleophile is strong enough to readily displace Br. 

Are you sure it says d)?


It looks more like a) to me. 

[Morgrothiel]

You are right, it is a, I looked at the wrong task

Thanks

[english]

You are right, it is a, I looked at the wrong task

Thanks

You understand why I chose a) right?

The alpha carbon in d) has more hindrance as ^-OH approaches.