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When pinacol is treated with dilute H(2)...

When pinacol is treated with dilute `H_(2)SO_(4)`, a re-arangement reaction takes place which leads to the formation of a ketone.
`CH_(3)-underset(CH_(3))underset(|)overset(OH)overset(|)C-underset(CH_(3))underset(|)overset(OH)C-CH_(3)overset(H_(2)SO_(4))rarrCH_(3)-underset(CH_(3))underset(|)overset(O)overset(||)C-overset(CH_(3))overset(|)C-CH_(5)`
This reaction involves re-arrangement of carbocation
Step 1:

`CH_(3)-underset(CH_(3))underset(|)overset(OH)overset(|)C-underset(CH_(3))overset(+)overset(OH_(2))overset(|)C-CH_(2)rarrCH_(3)-underset(CH_(3))underset(|)overset(OH)overset(|)C-underset(CH_(3))underset(|)overset(OH)overset(|)C-underset(CH_(3))underset(|)overset(+)C-CH_(3)`
Step 2:
Carbocation rearrange by hydride, alkyl shift to get as stable as they can. Stability is the driving force for re-arrangement migration of bond may also oC Cur. Where by ring expansion and ring contraction takes place. The relief of strain can provide a powerful driving force for re-arrangement.


What will be the product of following reaction
`CH_(3)-underset(H)underset(|)overset(OH)overset(|)C-underset(H)underset(|)overset(OH)overset(|)CH_(3)overset(H_(2)SO_(4))rarrQ`
Q is:

A

`CH_(3)-underset(O)underset(||)C-CH_(2)-CH_(3)`

B

`CH_(3)-underset(OH)underset(|)C=CH-CH_(3)`

C

Both

D

None

Text Solution

Verified by Experts

The correct Answer is:
A
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When pinacol is treated with dilute H_(2)SO_(4) , a re-arangement reaction takes place which leads to the formation of a ketone. CH_(3)-underset(CH_(3))underset(|)overset(OH)overset(|)C-underset(CH_(3))underset(|)overset(OH)C-CH_(3)overset(H_(2)SO_(4))rarrCH_(3)-underset(CH_(3))underset(|)overset(O)overset(||)C-overset(CH_(3))overset(|)C-CH_(5) This reaction involves re-arrangement of carbocation Step 1: CH_(3)-underset(CH_(3))underset(|)overset(OH)overset(|)C-underset(CH_(3))overset(+)overset(OH_(2))overset(|)C-CH_(2)rarrCH_(3)-underset(CH_(3))underset(|)overset(OH)overset(|)C-underset(CH_(3))underset(|)overset(OH)overset(|)C-underset(CH_(3))underset(|)overset(+)C-CH_(3) Step 2: Carbocation rearrange by hydride, alkyl shift to get as stable as they can. Stability is the driving force for re-arrangement migration of bond may also oC Cur. Where by ring expansion and ring contraction takes place. The relief of strain can provide a powerful driving force for re-arrangement. What will be the product of folowing reaction CH_(3)-underset(CH_(3))underset(|)overset(CH_(3))overset(|)C-CH_(2)-Broverset(NaOH)rarrP,P is:

Major product of the given reaction is CH_(3)-underset(CH_(3))underset(|)overset(CH_(3))overset(|)C-underset(CI)underset(|)(CH)-CH_(3)overset(C_(2)H_(5)O^-)rarr

CH_(3)-underset(CH_(3))underset(|)overset(CH_(3))overset(|)C-CH=CH-CH_(3)overset(H-Cl)(to) ?

The conversation : CH_(3)-underset(OH)underset(|)overset(CH_(3))overset(|)(C)-underset(OH)underset(|)overset(CH_(3))overset(|)(C)-CH_(3)underset(H_(2)SO_(4))overset("dil")rarrCH_(3)-underset(CH_(3))underset(|)overset(CH_(3))overset(|)(C)-underset(O)underset(||)(C)-CH_(3) is called :

The major product of the following reaction is: CH_(3)-underset(H)underset(|)overset(CH_(3))overset(|)C-underset(Br)underset(|)(CHCH_(3)) overset(CH_(3)OH) to

The following carbocation rearranges to CH_(2)=underset(CH_(3))underset(|)C-overset(CH_(3))overset(|)C-overset(o+)CH-overset(CH_(3))overset(|)(CH)-CH_(3)

The major product formed in the following reation is CH_(3)-underset(H)underset(|)overset(CH_(3))overset(|)C-CH_(2)-Br underset(CH_(3)OH)overset(CH_(3)ONa)rarr .

Give the IUPAC name of the compound CH_3-underset(CH_3)underset(|)CH-underset(OH)underset(|)CH-underset(CH_3)underset(|)overset(CH_3)overset(|)C-CH_3

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