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Question: Match the column- Column-I | Column-II ---|--- (A) Ph-CHO + $CH_2 \begin{matrix} \text{COOEt} \\ \t...

Match the column-

Column-IColumn-II
(A) Ph-CHO + CH2COOEtCOOEt→(1)EtONa(2)H3O⊕/ΔCH_2 \begin{matrix} \text{COOEt} \\ \text{COOEt} \end{matrix} \xrightarrow[]{\text{(1)EtONa} \\ \text{(2)H}_3\text{O}^\oplus \text{/}\Delta}(P) Perkin's reaction.
(B) Ph-CHO + CH2-COOCH3IBr→(1)Zn(2)H3O⊕/Δ\begin{matrix} \text{CH}_2\text{-COOCH}_3 \\ \text{I} \\ \text{Br} \end{matrix} \xrightarrow[]{\text{(1)Zn} \\ \text{(2)H}_3\text{O}^\oplus \text{/}\Delta}(Q) Reformatskii reaction.
(C) Ph-CHO + CH3_3COOCOCH3→(1)CH3COONa/Δ(2)H3O⊕/Δ_3 \xrightarrow[]{\text{(1)CH}_3\text{COONa/}\Delta \\ \text{(2)H}_3\text{O}^\oplus \text{/}\Delta}(R) Product is a carboxylic acid with aromatic ring within the same molecule.
(D) Ph-O∥C\begin{matrix} \text{O} \parallel \\ \text{C} \end{matrix}-O∥C\begin{matrix} \text{O} \parallel \\ \text{C} \end{matrix}-Ph + NaOH →(2)H⊕\xrightarrow[]{\text{(2)H}^\oplus}(S) Double bond equivalent of the product formed is less than or equal to 8.
(T) The major product cannot show optical isomerism
A

(A) - (R), (S), (T)

B

(B) - (Q), (R), (S), (T)

C

(C) - (P), (R), (S), (T)

D

(D) - (R), (T)

Answer

(A)-(R,S,T), (B)-(Q,R,S,T), (C)-(P,R,S,T), (D)-(R,T)

Explanation

Solution

Let's analyze each reaction in Column-I and match it with the descriptions in Column-II.

(A) Ph-CHO + CH2COOEtCOOEt→(1)EtONa(2)H3O⊕/ΔCH_2 \begin{matrix} \text{COOEt} \\ \text{COOEt} \end{matrix} \xrightarrow[]{\text{(1)EtONa} \\ \text{(2)H}_3\text{O}^\oplus \text{/}\Delta}

This is a Knoevenagel condensation between benzaldehyde and diethyl malonate. The product, after hydrolysis and decarboxylation, is Cinnamic acid (Ph-CH=CH-COOH).

  • (R) Product is a carboxylic acid with aromatic ring: Yes, Cinnamic acid.
  • (S) Double bond equivalent (DBE) of Cinnamic acid (C9H8O2): DBE = C + (N/2) - (H/2) + 1 = 9 + 0 - (8/2) + 1 = 9 - 4 + 1 = 6. 6 ≤\le 8. Yes.
  • (T) The major product cannot show optical isomerism: Cinnamic acid has no chiral center and is achiral. Yes.
  • (P) Perkin's reaction: No.
  • (Q) Reformatskii reaction: No.

Matches for (A): (R), (S), (T).

(B) Ph-CHO + CH2-COOCH3IBr→(1)Zn(2)H3O⊕/Δ\begin{matrix} \text{CH}_2\text{-COOCH}_3 \\ \text{I} \\ \text{Br} \end{matrix} \xrightarrow[]{\text{(1)Zn} \\ \text{(2)H}_3\text{O}^\oplus \text{/}\Delta}

This is a Reformatskii reaction between benzaldehyde and methyl α\alpha-bromoacetate. The intermediate β\beta-hydroxy ester undergoes hydrolysis and dehydration upon heating to form Cinnamic acid (Ph-CH=CH-COOH).

  • (Q) Reformatskii reaction: Yes.
  • (R) Product is a carboxylic acid with aromatic ring: Yes, Cinnamic acid.
  • (S) DBE of Cinnamic acid is 6. 6 ≤\le 8. Yes.
  • (T) The major product cannot show optical isomerism: Cinnamic acid is achiral. Yes.
  • (P) Perkin's reaction: No.

Matches for (B): (Q), (R), (S), (T).

(C) Ph-CHO + CH3_3COOCOCH3→(1)CH3COONa/Δ(2)H3O⊕/Δ_3 \xrightarrow[]{\text{(1)CH}_3\text{COONa/}\Delta \\ \text{(2)H}_3\text{O}^\oplus \text{/}\Delta}

This is a Perkin's reaction between benzaldehyde and acetic anhydride in the presence of sodium acetate. The product, after hydrolysis, is Cinnamic acid (Ph-CH=CH-COOH).

  • (P) Perkin's reaction: Yes.
  • (R) Product is a carboxylic acid with aromatic ring: Yes, Cinnamic acid.
  • (S) DBE of Cinnamic acid is 6. 6 ≤\le 8. Yes.
  • (T) The major product cannot show optical isomerism: Cinnamic acid is achiral. Yes.
  • (Q) Reformatskii reaction: No.

Matches for (C): (P), (R), (S), (T).

(D) Ph-O∥C\begin{matrix} \text{O} \parallel \\ \text{C} \end{matrix}-O∥C\begin{matrix} \text{O} \parallel \\ \text{C} \end{matrix}-Ph + NaOH →(2)H⊕\xrightarrow[]{\text{(2)H}^\oplus}

This is a Benzilic acid rearrangement of benzil (1,2-diketone) in the presence of a strong base. The product is Benzilic acid (Ph2C(OH)COOHPh_2C(OH)COOH).

  • (R) Product is a carboxylic acid with aromatic ring: Yes, Benzilic acid has two phenyl rings.
  • (T) The major product cannot show optical isomerism: Benzilic acid (Ph2C(OH)COOHPh_2C(OH)COOH) has a carbon bonded to two identical phenyl groups, a hydroxyl group, and a carboxyl group. It is achiral. Yes.
  • (S) DBE of Benzilic acid (C14H12O3): DBE = C + (N/2) - (H/2) + 1 = 14 + 0 - (12/2) + 1 = 14 - 6 + 1 = 9. 9 is not ≤\le 8. No.
  • (P) Perkin's reaction: No.
  • (Q) Reformatskii reaction: No.

Matches for (D): (R), (T).

Final Matching:

(A) - (R), (S), (T) (B) - (Q), (R), (S), (T) (C) - (P), (R), (S), (T) (D) - (R), (T)