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Organic Chemistry
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Q.1
WBCS Prelims 2017
Conversion of CH3C=CH to CH3CH=CH2
A. Lindlar catalyst
B. H2/Pd
C. NaBH4
D. LiAlH4
Explanation
Why Correct: Lindlar catalyst (Pd/CaCO3 with quinoline) hydrogenates alkynes specifically to cis-alkenes, preserving the double bond.
Distractor Analysis: H2/Pd (palladium on carbon) reduces alkynes completely to alkanes via intermediate alkenes. NaBH4 (sodium borohydride) reduces aldehydes, ketones, and acyl chlorides to alcohols but does not affect carbon-carbon triple bonds. LiAlH4 (lithium aluminum hydride) reduces carbonyl groups, carboxylic acids, and epoxides but not alkynes.
Takeaway: Sodium in liquid ammonia reduces alkynes to trans-alkenes via radical anion intermediates, contrasting with Lindlar's cis-addition.
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Q.2
WBCS Prelims 2017
Conversion of RBr to RMgBr requires
A. Mg /dry ether / N2 – atmosphere
B. Mg/ moist ether /N2 – atmosphere
C. Mg/ ethanol /N2 -atmosphere
D. Mg / dry ether /O2 – atmosphere.
Explanation
Why Correct: Grignard reagent synthesis demands magnesium metal in absolutely dry diethyl ether under inert nitrogen or argon atmosphere to preclude reaction with moisture or oxygen.
Distractor Analysis: Moist ether contains water that hydrolyzes Grignard reagents to alkanes. Ethanol has acidic protons that protonate Grignard reagents, yielding hydrocarbons. Oxygen atmosphere oxidizes Grignard reagents to alcohols, peroxides, or other oxygenated derivatives.
Takeaway: Grignard reagents act as potent nucleophiles that add to carbonyl compounds, forming alcohols after acidic aqueous workup.
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Q.3
WBCS Prelims 2017
The fastest SN1 reaction is of the followings:
(A) MeO — CH2 –Cl
(B) Me — CH2 -Cl
(C) Me –C –CH2 –Cl
(D) Ph — CH2 –CH2 – Cl
A. MeO — CH2 –Cl
B. Me — CH2 -Cl
C. Me –C –CH2 –Cl
D. Ph — CH2 –CH2 – Cl
Explanation
Why Correct: Methoxymethyl chloride (MeO-CH2-Cl) undergoes the fastest SN1 reaction because the methoxy group (-OCH3) strongly stabilizes the carbocation intermediate through resonance, making it more stable than carbocations from other options.
Distractor Analysis: Methyl chloride (Me-CH2-Cl) forms a primary carbocation, which is highly unstable. The structure Me-C-CH2-Cl appears incomplete but likely represents a tertiary carbocation, which is stable but less than resonance-stabilized ones. Phenethyl chloride (Ph-CH2-CH2-Cl) forms a benzylic carbocation, which is resonance-stabilized but less than the methoxymethyl carbocation.
Takeaway: In SN1 reactions, carbocation stability follows: resonance-stabilized (allylic/benzylic with electron-donating groups) > tertiary > secondary > primary > methyl, with -OCH3 providing exceptional stabilization.
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Q.4
WBCS Prelims 2015
Hybridization of C2 and C3 of propene (C1=C2-C3)
A. sp sp3
B. sp2 sp
C. sp2 sp2
D. sp sp
Explanation
Why Correct: C2 has three sigma bonds (one to C1, one to C3, one to H) and one pi bond to C1, requiring sp2 hybridization. C3 has four sigma bonds (one to C2, three to H), requiring sp3 hybridization.
Distractor Analysis: sp sp3 describes terminal alkyne carbons like in acetylene. sp2 sp describes a carbon with double bond adjacent to triple bond. sp sp describes two triple-bonded carbons like in acetylene.
Takeaway: In alkenes, the double-bonded carbon is always sp2 hybridized, while adjacent saturated carbons are sp3 hybridized.
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Q.5
WBCS Prelims 2013
Phenyl used in household work is a derivative of —
A. Methyl alcohol Chemistry
B. Tartaric acid
C. Benzene
D. Anthracene
Explanation
Why Correct: Phenyl (C6H5-) is the functional group derived from benzene by removing one hydrogen atom, and household phenyl disinfectants are typically phenol derivatives obtained from benzene.
Distractor Analysis: Methyl alcohol (methanol) is a simple alcohol used as solvent and fuel, not the source of phenyl groups. Tartaric acid is a dicarboxylic acid found in grapes, used in baking powder and winemaking. Anthracene is a polycyclic aromatic hydrocarbon with three fused benzene rings, used in dye production.
Takeaway: Phenol (C6H5OH) is the simplest aromatic alcohol and the parent compound of phenyl derivatives, with antiseptic properties that make it useful in disinfectants.
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Q.6
WBCS Prelims 2000
In the process of vulcanisation which two of the following are heated together?
A. Rubber and Sulphur
B. Latex and Sulphur
C. Rubber and Steel
D. Rubber and Lead
Explanation
Why Correct: Vulcanization heats natural rubber (polyisoprene) with elemental sulfur to create sulfur cross-links between polymer chains, enhancing elasticity and durability.
Distractor Analysis: Latex is the raw colloidal suspension from rubber trees, not the processed rubber used in vulcanization. Steel serves as reinforcement in tires but is not part of the vulcanization chemical process. Lead compounds were historically used as accelerators but are not the primary material heated with rubber.
Takeaway: Charles Goodyear discovered vulcanization in 1839, using 1-3% sulfur at 140-160°C for several hours to create disulfide bridges between polymer chains.
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Q.7
WBCS Prelims 2010
Which Carbohydrate is used commercially in the silvering of mirrors ?
A. Sucrose
B. Fructose
C. Cellulose
D. Glucose (C6H12O6)
Explanation
Why Correct: Sucrose hydrolyzes to glucose and fructose, with glucose reducing silver ions to metallic silver in the Tollens' reagent process, depositing a reflective silver layer on glass surfaces during mirror manufacturing.
Distractor Analysis: Fructose is fruit sugar with high sweetness but not the primary commercial source. Cellulose provides structural support in plant cell walls and is used in paper production. Glucose is the reducing sugar involved but is derived from sucrose hydrolysis in the commercial process.
Takeaway: The Tollens' test uses glucose to detect aldehydes, producing a silver mirror with ammoniacal silver nitrate solution, but commercial mirror production typically starts with sucrose.
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