Question Details

For the reaction sequence given below, the correct statement(s) is(are)


Options

A

P is optically active.

B

S gives Bayer’s test.

C

Q gives effervescence with aq. NaHCO3.

D

R is an alkyne.

Show Answer

Correct Answer :

Option C

Q gives effervescence with aq. NaHCO3.

Option B

S gives Bayer’s test.

Solution :

The correct statements for the given reaction sequence are:
Q gives effervescence with aq. NaHCO3.
S gives Bayer’s test.

Let us analyze the reaction sequence step-by-step:

1. Structure of the Starting Material:
The starting material shown in the image is a 6-membered lactone (cyclic ester) with a benzyl group (-CH2Ph) at the 4-position: 4-benzyltetrahydro-2H-pyran-2-one.

2. Conversion of the Lactone to P:
Treating the lactone with a strong reducing agent like lithium aluminium hydride (LiAlH4) reduces the cyclic ester group, opening the ring to yield a 1,5-diol:
LactoneLiAlH4P
The structure of P is:
HO-CH2-CH2-CH(CH2Ph)-CH2-CH2-OH
This is 3-benzylpentane-1,5-diol. Because the central carbon atom is bonded to two identical 2-hydroxyethyl groups (-CH2CH2OH), it is symmetric and lacks chiral centers. Thus, P is optically inactive.

3. Conversion of P to Q:
Jones reagent (CrO3-H2SO4) oxidizes both primary alcohol groups of P to carboxylic acids:
PCrO3-H2SO4Q
The structure of Q is a dicarboxylic acid:
HOOC-CH2-CH(CH2Ph)-CH2-COOH
Since Q is a carboxylic acid, it reacts with aqueous sodium bicarbonate (NaHCO3) to liberate carbon dioxide gas, producing effervescence:
R-COOH+NaHCO3R-COONa+H2O+CO2
Hence, the statement "Q gives effervescence with aq. NaHCO3" is correct.

4. Conversion of Q to R:
Heating Q with soda-lime (NaOH and CaO, Δ) results in decarboxylation (removal of both carboxyl groups as carbon dioxide):
QNaOH, CaO, ΔR
The structure of R is:
CH3-CH(CH2Ph)-CH3
which is isopropylbenzene (cumene). Since cumene is an alkylbenzene (aromatic hydrocarbon) and not an alkyne, the statement "R is an alkyne" is incorrect.

5. Conversion of P to S:
Heating the diol P with concentrated sulfuric acid (H2SO4) at 443 K causes acid-catalyzed dehydration. The two primary alcohol groups undergo elimination to form carbon-carbon double bonds:
PH2SO4, 443 KS
The structure of S is:
CH2=CH-CH(CH2Ph)-CH=CH2
Because S is an alkene (diene), it contains carbon-carbon double bonds and therefore reacts positively to Bayer’s test (decolorization of cold, dilute, alkaline potassium permanganate solution). Hence, the statement "S gives Bayer’s test" is correct.

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