You visited us 9 times! Enjoying our articles? Unlock Full Access!

Byju's Answer

Standard XII

Chemistry

Methods for Ester Synthesis

Diethyl malon...

Question

Diethyl malonate on treatment with one mole of $C_{2} H_{5} O N a$ followed by reaction with one mole of 5-bromoethyl pentanoate produces $A (C_{14} H_{24} O_{6})$ . A on heating with dilute $H_{2} S O_{4}$ yields $B (C_{7} H_{12} O_{4})$ . B on treatment with excess of $C_{2} H_{5} O H$ in presence of catalytic amount of $H_{2} S O_{4}$ yields $C (C_{11} H_{20} O_{4})$ . C on treatment with one mole of $E t O N a$ followed by workup with dilute HCl yields $D (C_{9} H_{14} O_{3})$ . D on further treatment with one mole $E t O N a$ followed by reaction with $C H_{3} I$ yields $E (C_{10} H_{16} O_{3})$ . E on heating with HCl yields 2-methylcyclohexanone. Deduce structures of A to E.

Open in App

Solution

Conc. $H_{2} S O_{4}$ wll break the ester bond
Further heat will remove one $C O O H$ group from compound A that will result in B

Suggest Corrections

Similar questions

Q. A hydrocarbon

A (C_{4} H_{8})

on reaction with

H C l

gives a compound

B (C_{4} H_{9} C l)

which on reaction with

1

mole of

N H_{3}

gives a compound

C (C_{4} H_{11} N)

. On reacting with

N a N O_{2}

and

H C l

(low temperature) followed by treatment with water, compound

C

yields optically active alcohol(s). Ozonolysis of

A (1 mole)

gives

2

moles of acetaldehyde.
The compound C is:

Q. 1,4 Pentadiene reacts with excess of

H C l

in the presence of benzoyl peroxide to give compound

X

, which upon reaction with excess of

M g

in dry ether forms

Y

. Compound

Y

on treatment with ethyl acelate followed by treatment with dilute acid yields

Z

. Identify the structure of compounds

X, Y

and

Z

Cyclohexene on ozonolysis followed by reaction with zinc dust and water gives compound E. Compound E on further treatment with aqueous KOH yields compound F. Compound F is

Q. An organic lactum A on acid hydrolysis produces B, an amino acid,.B on treatment with nitrous acid gives C. C on heating with concentrated

H_{2} S O_{4}

produces a lactone D. A can be synthesized by the reaction of cyclopentanone with hydroxylamine followed by treatment of product with concentrated

H_{2} S O_{4}

. Deduce structures of A to D.

Cyclohexene on reductive ozonalysis gives compound B. Compound ‘B’ on further treatment with aqueous NaOH followed by heating yields compound ‘C’. The compound ‘C’ is;

Join BYJU'S Learning Program

Conc. H2SO4 wll break the ester bond Further heat will remove one COOH group from compound A that will result in B

Conc. $H_{2} S O_{4}$ wll break the ester bond
Further heat will remove one $C O O H$ group from compound A that will result in B