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Chemistry Level 4

An alcohol

  • has 4 carbon and 1 oxygen atoms
  • gives white/colourless in Victor Mayer test.

Here are the sequential reactions carried out on it.

Reactions:

  • Add Cu to it and heat it to 350°C.
  • Then add B X 2 H X 6 / H X 2 O X 2 / O H \ce{B2H6} / \ce{H2O2} / OH^- .
  • Add PCC to it.
  • Then add isopropyl Magnesium Chloride to it followed by H + H^+
  • Add P 4 + B r 2 {P}_{4} + {Br}_{2} to it.
  • Now add B r X 2 ( 1 e q u i v a l e n t ) , h ν \ce{Br2} ( 1 equivalent ) , h\nu
  • Now add N a N H X 2 ( 1 e q u i v a l e n t ) \ce{NaNH2} (1 equivalent) . Consider the stable (major ) product.
  • Add Hypobromous acid to it.
  • Now add aq. KOH (excess ) to it.
  • Now add Methyl Magnesium Iodide to it in the presence of H + H^+ .
  • At last add H + H^+ to it.

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

Hints and Details

  • Every step of reaction will happen.
  • Consider the major products,
  • End product has a ketonic group.

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The answer is 128.

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2 solutions

Aniket Sanghi
Jun 10, 2016

A is the end product for this question .

Did exactly same:)

Samarth Agarwal - 5 years ago

Ch3mgx would not react as you did due to steric hindrance

Ravindra Singh Choudhary - 4 years, 11 months ago

And also when excess of aqueous of KOH is added, how could the Br be replaced by OH? OH- attacks from backside, which is nearly non-feasible due to already of a presence of OH which causes repulsion. Elimination will be more favorable when excess NaOH is added.

Ayushmaan Seth - 4 years, 8 months ago
Piyush Sethia
Jun 20, 2016

why the product after step 8 this

We take more stable product , and C+ is stable at tertiary Carbon! So OH will tend to attack at tertiary carbon

Although there is no formation of C+ but when bromine separates from the other C in mech ,there tend to develop a positive charge !!

Aniket Sanghi - 4 years, 12 months ago

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