Looking at this image, I can identify this as a Tamil-language chemistry question (likely from a Tamil Nadu board exam, 2023) asking which of the given compounds undergoes all three reactions (I, II, III):
- I. Reacts with PCl₅ to give a chloro compound
- II. Undergoes self-condensation in the presence of dilute NaOH
- III. Undergoes a reduction with LiAlH₄
Let me analyze each compound:
The Three Reactions:
Reaction I (PCl₅): PCl₅ reacts with -OH groups (alcohols, carboxylic acids) and -C=O groups (aldehydes, ketones, amides) - replacing O with Cl.
Reaction II (Dilute NaOH - Self Condensation): This is an Aldol condensation - requires an aldehyde or ketone with an α-hydrogen.
Reaction III (LiAlH₄ - Reduction): LiAlH₄ reduces aldehydes, ketones, carboxylic acids, esters, amides, and -CONH₂ groups.
Analyzing Each Compound:
Compound (1): CH₃-C(CH₃)(OH)-CH₂-CO-NH₂
- Has -OH → reacts with PCl₅ ✓
- Has -CONH₂ with α-H → can undergo aldol-type? No - amides don't do aldol condensation ✗
Compound (2): CH₃-CH(OH)-CH₂-CHO
- Has -OH → reacts with PCl₅ ✓
- Has -CHO with α-H → Aldol condensation ✓
- Has -CHO → LiAlH₄ reduces it ✓
- ALL THREE ✓
Compound (3): H-CO-C₆H₄-C(CH₃)₂-OH
- Has -OH → PCl₅ ✓
- Has -CHO (benzaldehyde type, no α-H due to aromatic ring) → No aldol ✗
Compound (4): CH₃-C(CH₃)(NH₂)-CH₂-CO-CH₃
- Has -NH₂, not -OH → PCl₅ reacts with -NH₂ but not the typical substitution
- Has ketone with α-H → Aldol ✓, LiAlH₄ ✓
- But the primary amine doesn't give the same PCl₅ reaction as -OH ✗
Compound (5): CH₃O-CO-C₆H₄-CH₂OH
- Has -CH₂OH → PCl₅ ✓
- Has ester group, no α-H aldehyde/ketone → No aldol condensation ✗
Answer: Compound (2) - CH₃-CH(OH)-CH₂-CHO
This compound (2-hydroxybutanal / 3-hydroxybutanal) satisfies all three conditions:
- The -OH group reacts with PCl₅ → chloro compound
- The -CHO with α-H undergoes aldol condensation with dilute NaOH
- The -CHO (and -OH) are reduced by LiAlH₄