Need Your Help for H NMR

[cutetina]

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Hi guys, I have joined this Forum recently because I am in a need of solution of this NMR Problem:
Compound A formula C10 H11Br - not react with bromine in dichloromethane but react with alcoholic potassium hydroxide to form compound B - Formula C10H10.
treatment of compound B with Potassium permanganate in sulfuric acid for a short period give the compound C - Formula C9H8O

The H-NMR of compound C shows this info:
3.0- 3.6 ppm (approx) - singlet - 4H
7.0- 7.4 ppm (approx) - singlet- 4H
treating compound B for a prolonged period with potassium permanganate in sulfuric acid gave compund D. formula- C8H6O4
the spectrum of the compound D suggest -OH group and -COO group.

Treatment of ferric bromide gave two compound E and F formula- C10H10Br2

 

[twester]

Hi guys, I have joined this Forum recently because I am in a need of solution of this NMR Problem:
Compound A formula C10 H11Br - not react with bromine in dichloromethane but react with alcoholic potassium hydroxide to form compound B - Formula C10H10.
treatment of compound B with Potassium permanganate in sulfuric acid for a short period give the compound C - Formula C9H8O

The H-NMR of compound C shows this info:
3.0- 3.6 ppm (approx) - singlet - 4H
7.0- 7.4 ppm (approx) - singlet- 4H
treating compound B for a prolonged period with potassium permanganate in sulfuric acid gave compund D. formula- C8H6O4
the spectrum of the compound D suggest -OH group and -COO group.

Treatment of ferric bromide gave two compound E and F formula- C10H10Br2

So what do you have so far?

 

[cutetina]

I got for compound A -> ph-CH2CH2BR and on para position cH=cH

Compound B-> ph-cH=CH2 and on para CH=CH2

For compound C ->

OR
3-Phenyl-2-propenal (cinnamaldehyde)
for compound D -> 1,3 Benz-dioic acid [ Ph-COOH and COOH on para]

FOR E and F ..I attached Br- group..but I m not sure about my answers..and I m confused about compound C If I see A and B..

I need the urgent help from u guys..pls help me out..!

Thanks In Advance

 

[YO YO YO]

Compound A formula C10 H11Br - not react with bromine in dichloromethane but react with alcoholic potassium hydroxide to form compound B - Formula C10H10.

when you say not react with Br2/Ch2Cl2, do you mean it stays purple? Because if it stays purple, then you can't possibly have an alkene in A.

From the way it sounds though, I am thinking that you mean that the compound A when treated with Br2/Ch2Cl2 turns clear.
Please clarify that

Also, is the sulfuric acid concentrated or dilute, and is it heated?

 

[Mongoos150]

Very confusing!