Benzene's Derivative

Chemistry Level 5

Consider the following compound:

It undergoes the following reactions with these reagents (in that order):

$t$ - $\ce{BuOK}$
$\ce{CHCl3}$ and $\ce{CH3ONa}$ , heat
$\ce{H3O+}$ and heat

If the final compound is $x$ -chloro $y, z$ dimethyl bromobenzene, what is the value of $x \times y \times z + 16?$

The answer is 40.

1 solution

Vitthal Yellambalse
Oct 20, 2016

The compound rearranges to:

The next set of reactions expand the pentane ring and remove $\ce{MeOH}$ , to give us:

This compound is 2-chloro 3,4-dimethyl bromobenzene.

Hence the answer is $\boxed{40}$

Please provide the mechanism of the 1st step.

Archit Agrawal - 4 years, 6 months ago

how did u do the first step please provide a mechanism

Zerocool 141 - 4 years, 6 months ago

Hey @Vitthal Yellambalse . , Can you please provide a mechanism , or roughly tell me the mechanism involved in the 1st step . I got it right but I guess I did 1st step wrong! Thanks :)

Aniket Sanghi - 4 years, 4 months ago

@Vitthal Yellambalse

Aniket Sanghi - 4 years, 1 month ago

@Aniswar S K @Spandan Senapati

Can you please give some hint?

Harsh Shrivastava - 4 years ago

i got 2,3 dimethyl 5 chloro bromo benzene

Aniswar S K - 3 years, 11 months ago

OK how did you proceed?

Harsh Shrivastava - 3 years, 11 months ago

@Harsh Shrivastava – First i did isomerization with the base.

Then the carbene added across the double bond.

Then the base takes up a proton, the double bond is formed, one of the bond of the cyclopropane ring is broken to form a double bond sending the chlorine out

then i did ring expansion, and protonated the och3, it leaves and an alkene is formed.

Aniswar S K - 3 years, 11 months ago

Benzene's Derivative

The answer is 40.

1 solution

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