wiz-icon
MyQuestionIcon
MyQuestionIcon
1
You visited us 1 times! Enjoying our articles? Unlock Full Access!
Byju's Answer
Standard XII
Chemistry
Fischer's Esterification Process
Solve this : ...
Question

Solve this :

13. An organic compound A C5H8O3 on heating with soda lime gives B which reacts with HCN to give C. The compound C reacts with thionyl chloride to produce D which on reaction with KCN gives a compound E. Alkaline hydrolysis of E gives a salt F which on heating with soda lime produces n-butane. Careful oxidation of A with dichromate gives acetic acid and malonic acid. Give the structures from A to F with proper reason .

Open in App
Solution

Dear Student,

The step by step reactions are as follows.

As given on oxidation of A with dichromate it gives acetic acid and malonic ester that gives the information of the presence of an acid and ether group in A and as molecular formula of A is C5H8O3.
The reaction is as follows :
CH3COCH2CH2COOH →K2Cr2O7CH3COOH + HOOCCH2COOH
(i) So, A will be CH3COCH2CH2COOH.

Now on heating A with sodalime it undergo decarboxylation to give B.
The reaction is as follows :
CH3COCH2CH2COOH →sodalime / decarboxylationCH3CH2COCH3 + CO2
(ii) So, B will be CH3CH2COCH3.

Now B reacts with HCN undergo nucleophilic addition reaction over aldehyde .
The reaction is as follows :
CH3CH2COCH3 →HCN CH3CH2C(CN)(OH)CH3
(iii) So, C will be ​​CH3CH2C(CN)(OH)CH3

Now, C reacts with Thionyl chloride to give D : Nucleophilic susbstitution :
The reaction is as follows:
CH3CH2C(CN)(OH)CH3→SOCl2CH3CH2C(CN)(Cl)CH3
(iv) So, D will be CH3CH2C(CN)(Cl)CH3

Now , D reacts with KCN to give E : Nucleophilic substitution :
The reaction is as follows:
CH3CH2C(CN)(Cl)CH3→KCNCH3CH2C(CN)(CN)CH3
(v) So, E will be CH3CH2C(CN)(CN)CH3

Now, E on alkaline hydrolysis gives F :
The reaction is as follows:
CH3CH2C(CN)(CN)CH3→H2O/NaOHCH3CH2C(CH3) (COONa)2
(vi) So, F will be ​CH3CH2C(CH3) (COONa)2

Regards

flag
Suggest Corrections
thumbs-up
0
similar_icon
Similar questions
Q. An organic compound A(C9H8O3) does not react with an aqueous solution of NaHCO3 and does not change the color of litmus paper. A on acid hydrolysis gives B(C9H8O4) whereas A on treatment with methanol in acid medium gives C(C10H14O4) as the major alcoholysis product. B on heating with excess of soda-lime produces toluene. Deduce structures of A to C.
Q. An organic compound (A) gives positive Liebermann reaction and on treatment with CHCl3/KOH followed by hydrolysis gives (B) and (C) ,. Compound (B) gives colour with Schiff's reagent but not (C), which is steam - volatile. (C) on treatment with LIAlH4 gives (D), C7H8O2 which on oxidation gives 9E), Compound (E) reacts with (CH3CO)2O/CH3COOH to give a pain - reliever (F), Give structure of (A) to (F) with proper reasoning.
Q. An organic compound (A) on heating produces two gases (B) and (C) and neutral oxide (D) which turns cobalt chloride paper pink. Gas (B) turns lime water milky and produces an acidic solution, with water. Gas (C) produces a poisonous gas (E) with chlorine gas, this gas with ammonia gives an organic compound (F) which on further reaction with (D) gives NH3 gas. Then, compounds (A) and (F) can be found as:
Q. Propyl lithium reacts with ethene to give a compound (A) which on reaction with methanal followed by acidic hydrolysis gives compound (B) is:
Q. p-Cresol reacts with chloroform in alkaline medium to give the compound A which adds hydrogen cyanide to form the compound B. The latter on acidic hydrolysis gives chiral carboxylic acid. The structure of the carboxylic acid is

View More
Join BYJU'S Learning Program
similar_icon
Related Videos
thumbnail
lock
Esters
CHEMISTRY
Watch in App
explore_more_icon
Explore more
Fischer's Esterification Process
Standard XII Chemistry
Join BYJU'S Learning Program
book_image
AI Tutor
book_image
Textbooks
book_image
Question Papers
book_image
Install app
CrossIcon