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)