Organic chemistry 18!

Chemistry Level 4

You Have Nitrobenzene (A).

When A Is treated with Tin in HCl it yields a compound B.

B Is Treated with Acetyl Chloride to give C. \

C is treated with Concentrated Sulphuric Acid to give D.

D Is treated with Nitric Acid to give E.

E Is treated with Dilute Sulphuric Acid And Heated to give F.

Finally F Is treated Aqueous KOH To give G.

Enter Molecular Mass of the compound G to the nearest integer

The answer is 138.

2 solutions

Neelesh Vij
May 3, 2016

B is aniline

C is $\ce{C_6H_5NH(CO)CH_3}$

D is C compound with $\ce{-SO_3H}$ at para position

E is C compound with $\ce{-NO_2}$ at ortho position wrt $\ce{NH(CO)CH_3}$

F will be benzene with $\ce{-NH_2}$ and $\ce{-NO_2}$ with positions ortho to each other which has molecular mass of $\boxed{138}$

Bro actually your solution is a bit wrong .

D when treated with nitric acid will NO2 At meta position wrt SO3H Group ie ortho to NHCOCH3

Prakhar Bindal - 5 years, 1 month ago

Are you sure of that?

I think its a case of ipso substitution where $\ce{-SO_3}$ gas escapes and then attacking group attacks at an available position.Please correct if i am going wrong

neelesh vij - 5 years, 1 month ago

Bro SO3H is a good leaving group i know but it escapes in the presence of dilute acid or base only

Prakhar Bindal - 5 years, 1 month ago

@Prakhar Bindal – So please post your solution i am deleting mine!

neelesh vij - 5 years, 1 month ago

@Neelesh Vij – Bro check this out from 14:30

https://www.youtube.com/watch?v=qeVsa91afig&index=7&list=PLtfEipLJrhIE91Y0O1J5f5oArKypj2zG1

Prakhar Bindal - 5 years, 1 month ago

@Prakhar Bindal – Hmm.. mine was a close one.. Luckily molecular mass remained same :P

neelesh vij - 5 years, 1 month ago

won't conc. h2so4 cause dehydration ? in C ?

hiroto kun - 4 years, 2 months ago

DAI LOUDE Aqueous KOH yenga Da add panne?

Sidharth Shambu - 3 years, 4 months ago

Siddharth Shourya
May 30, 2016

First of all nitrobenzene will get reduce to aniline after that on reacting with acetyl chloride formation of acetanilide(CH3CONHC6H5)+ HCl will be formed on further reacting with conc.sulphuric acid + nitric acid acetanilide forms actually 3 compounds that are: 1::- 4 nitro acetanilide (major), 2 nitroacetanilide (minor), small amounts of 2,4 di nitroacetanilide. On further reaction with dilute sulphuric acid hydrolysis takes place which result in formation of nitroaniline(para.ortho ) thus of the formula C6H6N2O2 having moleculer mass 138

Organic chemistry 18!

The answer is 138.

2 solutions

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