Question

2.Which of the alcohols listed below would you expect to react most rapidly with PBr3?A)CH3CH2CH2CH2CH2CH2OHB)(CH3CH2)2CH(OH)CH2CH3C)(CH3CH2)2CHOHCH3D)(CH3CH2)3COHE)(CH3CH2)2C(CH3)OH

Answer 1

Answer:

A) CH3CH2CH2CH2CH2CH2OH

Explanation:

For this question, we have the following answer options:

A) CH3CH2CH2CH2CH2CH2OH

B) (CH3CH2)2CH(OH)CH2CH3

C) (CH3CH2)2CHOHCH3

D) (CH3CH2)3COH

E) (CH3CH2)2C(CH3)OH

We have to remember the reaction mechanism of the substitution reaction with $PBr_3$. The idea is to generate a better leaving group in order to add a "Br" atom.

The $PBr_3$ attacks the "OH" generation new a bond to P (O-P bonds are very strong), due to this new bond we will have a better leaving group that can remove the oxygen an allow the attack of the Br atom to generating a new C-Br bond. This is made by an Sn2 reaction. Therefore we will have a faster reaction with primary substrates. In this case, the only primary substrate is molecule A. So, "CH3CH2CH2CH2CH2CH2OH" will react faster.

See figure 1

I hope it helps!