Organic is Fun!

Chemistry Level 3

Take the famous compound Benzene

Then carry out the following reactions sequentially.

Reactions

  • Add propyl chloride to it in presence of A l C l X 3 \ce{AlCl3} .
  • Heat it to 130°C in presence of O 2 {O}_{2} followed by H + H^+ .
  • Now, add C H X 3 C O C l \ce{ CH3COCl} , in it in the presence of base.

Enter your answer as the Molecular weight of the end product.

Hints and Details

  • Every step of reaction will happen.
  • Consider only the major products.

Started with a simple one ! :)

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The answer is 136.

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1 solution

Aniket Sanghi
Jun 10, 2016

In the 1st step cumene will form , in the next step phenol will form and in the last step CH3-COO-ph

Mention H X 3 O X + \ce{H3O^+} in second step otherwise in second step product will not be phenol , it will be cumene hydroperoxide

Harsh Gupta - 5 years ago

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No H+ it is free radical reaction

Aniket Sanghi - 5 years ago

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Cumene (isopropylbenzene) is oxidised in the presence of air to cumenehydroperoxide (This is free radical reaction ). Then it is converted to phenol and acetone by treating it with dilute acid (rearrangement reaction)

For Mechanism

Harsh Gupta - 5 years ago

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@Harsh Gupta Yup you are right :)

Aniket Sanghi - 5 years ago

sir, cumene will not be formed if you took n-propyl but only if you took 2-propyl chloride :) pl, mention it.

hiroto kun - 4 years, 4 months ago

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Cumene do form as there a carbocation intermediate is formed which do rearranges .

Aniket Sanghi - 4 years, 4 months ago

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oh , thank you sir :)

hiroto kun - 4 years, 4 months ago

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@Hiroto Kun Hey why calling me sir ? I am the same age as you!

Aniket Sanghi - 4 years, 4 months ago

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