A hydrocarbon (A) with molecular formula C5H10 on ozonolysis gives two products (B) and ( C). Both (B)………………….

Question 38:A hydrocarbon (A) with molecular formula C5H10 on ozonolysis gives two products (B) and ( C). Both (B) and (C) give a yellow precipitate when heated with iodine in presence of NaOH while only (B) give a silver mirror on reaction with Tollen’s
reagent.

a. Identify (A), (B) and (C).
b. Write the reaction of B with Tollen’s reagent
c. Write the equation for iodoform test for C
d. Write down the equation for aldol condensation reaction of B and C.

The correct answer is – A is an alkene
B is an aldehyde with –CH3 group
C is a methyl ketone
CH3CHO + [Ag(NH3)2]
++ OH-
CH3COO-
+ Ag + NH3 + H2O (1/2)
CH3COCH3 + NaOH + I2 CHI3 + CH3COONa (1/2)
A : CH(CH3)=C(CH3)2 B: CH3CHO C: O=C(CH3)2 (1.5 = 1/2 each)
CH3COCH3 + CH3CHO
Ba(OH)2
(CH3)2C(OH)CH2COCH3 + CH3CH(OH)CH2CHO + (CH3)2C(OH)CH2CHO
+ CH3CH(OH)CH2COCH3

heat
(CH3)2C=CHCOCH3 + CH3CH=CHCHO + (CH3)2C=CHCHO
+ CH3CH=CHCOCH3 ( 2.5 = 1/2 mark for each product, ½ for the reaction)