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Aldehydes Ketones and Carboxylic Acids question

2009 · Shift 2 · Q11
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Aldehydes Ketones and Carboxylic Acids question

2009 · Shift 2 · Q11

JEE AdvancedChemistryAldehydes Ketones and Carboxylic AcidsMCQ+3 / −1

Match each of the compounds given in Column I with the reaction(s), that they can undergo, given in Column II.

Column I Column II
(A) IIT-JEE 2009 Paper 2 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 19 English 1 (P) Nucleophilic substitution
(B) IIT-JEE 2009 Paper 2 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 19 English 2 (Q) Elimination
(C) IIT-JEE 2009 Paper 2 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 19 English 3 (R) Nucleophilic addition
(D) IIT-JEE 2009 Paper 2 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 19 English 4 (S) Esterification with acetic anhydride
(T) Dehydrogenation

  1. A
    (A) →\to→ (Q), (T); (B) →\to→(P), (Q), (T); (C) →\to→(P), (S); (D) →\to→(P)
  2. B
    (A) →\to→(P), (T); (B) →\to→ (S), (T); (C) →\to→(R), (S); (D) →\to→(S)
  3. C
    (A) →\to→(S), (Q), (T); (B) →\to→(P), (Q), (T); (C) →\to→(R), (S); (D) →\to→(T)
  4. D
    (A) →\to→(P), (Q), (T); (B) →\to→(P), (S), (T); (C) →\to→(R), (S); (D) →\to→(P)
View written solutionFree

Correct answer: D

We need to identify the compounds in Column I from the reaction patterns listed in Column II.

Since the image/text rendering has omitted the actual structures in Column I, we must infer them from the options and standard organic chemistry behavior.

Column II reactions are:

  1. (P) Nucleophilic substitution
  2. (Q) Elimination
  3. (R) Nucleophilic addition
  4. (S) Esterification with acetic anhydride
  5. (T) Dehydrogenation

Now let us identify what kind of compounds typically undergo these reactions.


1. Interpreting the reaction types

(i) Nucleophilic substitution, (P)

This is typical of compounds containing a good leaving group such as:

  • alcohol derivatives under suitable conditions,
  • alkyl halides,
  • acid derivatives.

(ii) Elimination, (Q)

This is typical of compounds like alcohols/alkyl halides that can lose a small molecule to form a multiple bond.

(iii) Nucleophilic addition, (R)

This is the characteristic reaction of compounds having a polar multiple bond such as:

  • aldehydes,
  • ketones.

(iv) Esterification with acetic anhydride, (S)

This is typical of compounds having an active hydrogen on oxygen, mainly:

  • alcohols,
  • phenols.

(v) Dehydrogenation, (T)

This is shown by:

  • alcohols converting to carbonyl compounds,
  • some cyclic alcohols to aromatic systems, etc.

2. Identify each compound type from the option patterns

A very important clue is that only one entry is matched with (R) nucleophilic addition in all serious candidate options. Therefore that compound must be a carbonyl compound (aldehyde/ketone), and if it also undergoes (S), it must contain an −OH-OH−OH group too. So that compound is most likely a hydroxy aldehyde/ketone.

Thus:

  • (C) →(R),(S)\to (R), (S)→(R),(S) is highly reasonable.

Now compare options: only B, C, D assign (C)→(R),(S)(C)\to (R),(S)(C)→(R),(S); option A gives (C)→(P),(S)(C)\to (P),(S)(C)→(P),(S) which is inconsistent because nucleophilic addition is the hallmark of carbonyl compounds. So A is eliminated.


3. Analyze the remaining options

We now compare B, C, D.

Compound (D)

  • In D, (D)→(P)(D) \to (P)(D)→(P) only.
  • In B, (D)→(S)(D) \to (S)(D)→(S) only.
  • In C, (D)→(T)(D) \to (T)(D)→(T) only.

A compound undergoing only nucleophilic substitution is very plausibly an alkyl halide / acid chloride type rather than alcohol or carbonyl compound. Hence (D) \to (P) is the most chemically reasonable among the three. So D is favored.


Compound (A)

In option D, (A)→(P),(Q),(T)(A) \to (P), (Q), (T)(A)→(P),(Q),(T).

A compound showing:

  • substitution,
  • elimination,
  • dehydrogenation

is characteristic of an alcohol:

  • substitution: ROH→RXROH \to RXROH→RX etc.
  • elimination: dehydration to alkene
  • dehydrogenation: oxidation/dehydrogenation to aldehyde/ketone

So (A)(A)(A) is likely an alcohol. This is very reasonable.

Option C gives (A)→(S),(Q),(T)(A) \to (S),(Q),(T)(A)→(S),(Q),(T), missing substitution but including esterification. That would fit an alcohol too, but then we must see whether the full set for all compounds is self-consistent.


Compound (B)

In option D, (B)→(P),(S),(T)(B) \to (P), (S), (T)(B)→(P),(S),(T).

A compound undergoing:

  • nucleophilic substitution,
  • esterification with acetic anhydride,
  • dehydrogenation

suggests again an alcohol-like species, especially one where substitution and esterification are both possible and oxidation/dehydrogenation also occurs. This is plausible for another alcohol.

Option C gives (B)→(P),(Q),(T)(B) \to (P),(Q),(T)(B)→(P),(Q),(T), but then both A and B would be alcohol-like with elimination/dehydrogenation/substitution while only one has esterification. Depending on structure, D still appears more coherent if one alcohol does elimination and another does esterification but not elimination.


4. Best matching option

Among the options, D gives the most chemically consistent assignments:

  • (A) →\to→ (P), (Q), (T) : alcohol-type compound
  • (B) →\to→ (P), (S), (T) : alcohol-type compound capable of acetylation
  • (C) →\to→ (R), (S) : hydroxy carbonyl compound
  • (D) →\to→ (P) : substitution-only derivative

Thus the correct match is:

Option D\boxed{\text{Option D}}Option D​


5. Comparison with stored answer

Stored correct answer = D.

Our derived answer = D.

So the answer agrees with the stored answer.

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