Aldehydes, Ketones and Carboxylic Acids · Question 8

Monocyclic compounds P, Q, R and S are the major products formed in the reaction sequences given below. [figure] The product having the highest number of unsaturated carbon atom(s) is

1. P
2. Q
3. R
4. S

Reaction of iso-propylbenzene with O2 followed by the treatment with H3O+ forms phenol and a by-product P. Reaction of P with 3 equivalents of Cl2 gives compound Q. Treatment of Q with Ca(OH)2 produces compound R and calcium salt S. The correct statement(s) regarding P, Q, R and S is(are)

1. Reaction of P with R in the presence of KOH followed by acidification gives [figure]
2. Reaction of R with O2 in the presence of light gives phosgene gas
3. Q reacts with aqueous NaOH to produce Cl3CCH2OH and Cl3CCOONa
4. S on heating gives P

Complete reaction of acetaldehyde with excess formaldehyde, upon heating with conc. NaOH solution, gives P and Q. Compound P does not give Tollens’ test, whereas Q on acidification gives positive Tollens’ test. Treatment of P with excess cyclohexanone in the presence of catalytic amount of p-toluenesulfonic acid (PTSA) gives product R. Sum of the number of methylene groups (-CH2-) and oxygen atoms in R is .

List-I contains various reaction sequences and List-II contains the possible products. Match each entry in List-I with the appropriate entry in List-II and choose the correct option.

1. P-3, Q-5, R-4, S-1
2. P-3, Q-2, R-4, S-1
3. P-3, Q-5, R-1, S-4
4. P-5, Q-2, R-4, S-1

In the following reaction sequence, the major product P is formed. [figure] Glycerol reacts completely with excess P in the presence of an acid catalyst to form Q. Reaction of Q with excess NaOH followed by the treatment with CaCl2 yields Ca-soap R, quantitatively. Starting with one mole of Q, the amount of R produced in gram is . [Given, atomic weight: H = 1, C = 12, N = 14, O = 16, Na = 23, Cl = 35, Ca = 40]

The option(s) with correct sequence of reagents for the conversion of P to Q is(are) [figure]

1. i) Lindlar’s catalyst, H2; ii) SnCl2/HCl; iii) NaBH4; iv) H3O+
2. i) Lindlar’s catalyst, H2; ii) H3O+; iii) SnCl2/HCl; iv) NaBH4
3. i) NaBH4; ii) SnCl2/HCl; iii) H3O+; iv) Lindlar’s catalyst, H2
4. i) Lindlar’s catalyst, H2; ii) NaBH4; iii) SnCl2/HCl; iv) H3O+

Sum of number of oxygen atoms in S and T is .