DAT Destroyer (2010) #52 Ochem question:

This forum made possible through the generous support of SDN members, donors, and sponsors. Thank you.

Kaka89

Full Member
10+ Year Member
Joined
Jun 23, 2009
Messages
14
Reaction score
0
I don't understand why the answer is "C". Isn't it true that an E2 reactions typically require primary or secondary alkyl halides, then why would the tertiary halide be the most reactive?!

please help! Thanks 🙂
 
Sn2 reactions favor primary and secondary. that being said the opposite is true for E2 rxns.

so if you have a tertiary alkyl halide it wouldn't react by means of Sn2 so it would then favor E2. thus making a tertiary more favorable.
 
I don't understand why the answer is "C". Isn't it true that an E2 reactions typically require primary or secondary alkyl halides, then why would the tertiary halide be the most reactive?!

please help! Thanks 🙂

Edit: Quick thing, E2 can react with tertiary, secondary, or primary alkyl halides, typically they react with tertiary > secondary though. Explanation below.

First off, we aren't going to worry about what might be reacting with our substrates, our reactivity will solely be based on the substrate and its leaving group in this problem (assume a strong base, since it is required).

Okay, our substrate or electrophile. What do we want with E2? We want to form the most substituted alkene possible (most stable). So looking at our choices, "A" clearly forms the most substituted alkene (more substituted alkyl halide, more substituted alkene usually). So we automatically know "A" is most reactive.

Remember we aren't worried about attacking like in Sn2, thus we aren't worried about steric hindrance. Next are our two secondary alkyl halides (B and C), which has the better leaving group? Iodine, so our order is now A>B>C. Same thing with choices D and E, Bromine is the better leaving halide than Chlorine, so our answer is "C".

Anyway, the key point to remember here is that with E2 you want the most substituted alkene product possible.

Cheers
 
Primary halides prefer to do Substitution reactions. More energy is needed for an elimination. E2 reactions go fastest with tertiary molecules. If the base is very strong, such as ethoxide....a secondary will react. A primary never gives E2 unless a big base such as t-butoxide is used.

good luck
 
Thanks guys - I thought (for some reason) the same conditions applied for Sn2 and E2 except that E2 needed a strong base, but it makes sense that you would want the most substituted product (an alkene) to be formed, so my thinking can't be true!!

Thanks again!
 
Top