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Aldehydes, Ketones and Carboxylic Acids · Question 11

JEE Advanced 2024 Paper 1NumericalMedium📈 Topic in 17% papers+4
1

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 .

Answer

18

Solution

Three crossed aldol additions (HCHO has no α-H, acetaldehyde gives all three α-H):

[figure] 3HCHO, OH- [figure]

Crossed Cannizzaro with HCHO (HCHO is oxidised, the other aldehyde reduced):

[figure] HCHO, conc. NaOH, [figure] (P) + HCOONa (Q)

P has no CHO – no Tollens’ test; Q on acidification gives HCOOH, which gives Tollens’ test.

Each 1,3-diol pair of P forms a 1,3-dioxane ketal with one cyclohexanone:

[figure] [PTSA, -2H2O]excess cyclohexanone [figure] (R)

-CH2- groups: 4 (from P) + 2 × 5 (two cyclohexane rings) = 14; O atoms = 4.

Sum = 14 + 4 = 18

Answer: 18

JEE Advanced 2024 Paper 1

Keep practising — Aldehydes, Ketones and Carboxylic Acids

2

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
JEE Advanced 2024 Paper 1
3

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]

JEE Advanced 2024 Paper 1
4

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+
JEE Advanced 2024 Paper 2
5

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

JEE Advanced 2024 Paper 2

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