Thank you for registering.

One of our academic counsellors will contact you within 1 working day.

Please check your email for login details.
MY CART (5)

Use Coupon: CART20 and get 20% off on all online Study Material

ITEM
DETAILS
MRP
DISCOUNT
FINAL PRICE
Total Price: Rs.

There are no items in this cart.
Continue Shopping

Give the migratory order for pinacol pinacolone reactions?

Give the migratory order for pinacol pinacolone reactions?

Grade:Select Grade

1 Answers

Bhavya
askIITians Faculty 1281 Points
5 years ago

In the pinacol rearrangement, a 1,2-diol is treated with acid and rearranges to a carbonyl compound in the following manner :

505-2301_pinacol rearrangement.PNG

migratory aptitude of groups in pinacol-pinacolone rearrangement is:

H>Ph>Me3C>MeCH2>Me

The reason this kind of migration occurs are:-
1) help stabilize the developing carbocation center
2) once fully migrated, produces a resonance stabilized hydroxyl-carbocation.

Generally, both hydroxyls will protonate and lead to separate products. In terms of which group will migrate, the only thing agreed upon is that a tertiary carbon will migrate in preference to a secondary carbon which will migrate in preference to a primary carbon.Clearly, the ability of the migrating group to stabilize positive charge plays a role.

Think You Can Provide A Better Answer ?

Provide a better Answer & Earn Cool Goodies See our forum point policy

ASK QUESTION

Get your questions answered by the expert for free