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Organic Chemistry
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Q.1
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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Q.2
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.3
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.4
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.5
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.6
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.7
WBCS Prelims 2001
Phosgene is a common name of
A. phosphorus trichloride
B. phosphorus oxychloride
C. phosphine
D. Carbonyl dichloride
Explanation
Why Correct: Phosgene is the common name for carbonyl dichloride (COCl2), a highly toxic gas used historically as a chemical weapon and industrially in polymer production.
Distractor Analysis: Phosphorus trichloride (PCl3) is a colorless liquid used as a chlorinating agent. Phosphorus oxychloride (POCl3) is a colorless liquid used as a chlorinating agent and in semiconductor manufacturing. Phosphine (PH3) is a toxic, flammable gas used as a fumigant and in semiconductor doping.
Takeaway: Phosgene's chemical formula COCl2 reveals it contains carbon, oxygen, and chlorine, distinguishing it from phosphorus compounds.
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Q.8
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.9
WBPSC Miscellaneous Prelims 2012
Saturated hydrocarbons are termed paraffins because
A. they are much less reactive
B. they are highly reactive
C. they are insoluble in water
D. they are noncombustible
Explanation
Why Correct: The word ‘paraffin’ comes from Latin ‘parum affinis’ meaning ‘little affinity’, referring to the low chemical reactivity of alkanes. Saturated hydrocarbons have only single bonds, making them much less reactive than unsaturated hydrocarbons.
Distractor Analysis: Highly reactive describes alkenes/alkynes, not alkanes. Insolubility in water is a property of many hydrocarbons but not the reason for the name. Noncombustible is false – saturated hydrocarbons burn readily in oxygen.
Takeaway: Alkanes are also called paraffins; alkenes are olefins. The term directly relates to reactivity, not solubility or combustibility.
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Q.10
WBPSC Miscellaneous Prelims 2011
Rectifying Spirit is a
A. Mixture of 95% ethanol + 5% methanol
B. Mixture of 95% ethanol + 5% water
C. Mixture of 95% ethanol + 5% pyridine
D. 100% ethanol
Explanation
Why Correct: Rectified spirit is defined as a mixture of 95% ethanol and 5% water by volume, achieved by fractional distillation.
Distractor Analysis: 95% ethanol + 5% methanol describes methylated spirit, which is toxic due to methanol. 95% ethanol + 5% pyridine is used as denatured spirit, not rectified spirit. 100% ethanol is absolute alcohol, obtained by further dehydration using azeotropic distillation.
Takeaway: Rectified spirit contains 95% ethanol and 5% water; common confusion with absolute alcohol (99.9% ethanol) and denatured spirit (ethanol with additives like methanol or pyridine).
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Q.11
WBPSC Miscellaneous Prelims 2009
Urea was the first Organic compound synthesized in laboratory by
A. Lavoisier
B. Wohler
C. Berzelius
D. Pasteur
Explanation
Why Correct: Friedrich Wohler synthesized urea from ammonium cyanate in 1828, refuting vitalism and demonstrating organic compounds can be made from inorganic precursors.
Distractor Analysis: Lavoisier is father of modern chemistry but not urea synthesis. Berzelius was Wohler's mentor and proposed vitalism. Pasteur worked on fermentation and pasteurization.
Takeaway: Wohler synthesis (1828) is a landmark event in organic chemistry. Vitalism vs mechanism.
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Q.12
WBPSC Miscellaneous Prelims 2009
Which acid of the following is the strongest?
A. HCOOH
B. ClCH2COOH
C. FCH2CH2COOH
D. CH3COOH
Explanation
Why Correct: ClCH2COOH is the strongest due to the powerful electron-withdrawing inductive effect of the chlorine atom on the alpha carbon, which stabilizes the conjugate base. The effect decreases with distance, so FCH2CH2COOH has a weaker effect despite fluorine's higher electronegativity.
Distractor Analysis: HCOOH (formic acid) is a weak organic acid, stronger than acetic acid but weaker than chloroacetic. FCH2CH2COOH has fluorine on the beta carbon, so the inductive effect is significantly attenuated compared to the alpha position. CH3COOH (acetic acid) is the weakest due to the electron-donating methyl group.
Takeaway: The closer the electron-withdrawing group to the carboxyl group, the stronger the acid. Alpha-halo acids are stronger than beta-halo acids. Chloroacetic acid (pKa ~2.9) is stronger than formic acid (pKa ~3.8) and acetic acid (pKa ~4.8).
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Q.13
WBPSC Miscellaneous Prelims 2008
In the alkane series methane is followed by:
A. Propane
B. Butane
C. Benzene
D. Ethane
Explanation
Why Correct: Alkanes are saturated hydrocarbons with general formula CnH2n+2. Methane (CH4) is the first member, ethane (C2H6) is the second member, so methane is immediately followed by ethane.
Distractor Analysis: Propane (C3H8) is the third alkane after ethane. Butane (C4H10) is the fourth. Benzene (C6H6) is an aromatic hydrocarbon, not an alkane.
Takeaway: Memorize the first five alkanes: methane (C1), ethane (C2), propane (C3), butane (C4), pentane (C5). A common exam follow-up is asking the formula or successor.
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Q.14
WBPSC Miscellaneous Prelims 2008
Organic compound used for welding and artificially ripening of fruits is:
A. CH4
B. C2H6
C. C2H2
D. C2H4
Explanation
Why Correct: Acetylene (C2H2) is used in oxyacetylene welding due to its high combustion temperature. It is also used for artificial ripening of fruits as a plant growth regulator that mimics ethylene, accelerating the ripening process.
Distractor Analysis: Methane (CH4) is a fuel gas but not used for welding or ripening. Ethane (C2H6) is a minor component of natural gas. Ethylene (C2H4) is the natural plant hormone for ripening but is not used for welding; acetylene is the compound commonly cited for both applications in exams.
Takeaway: Remember: Oxyacetylene flame for welding, calcium carbide (CaC2) reacts with water to give acetylene used for illegal fruit ripening.
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Q.15
WBPSC Miscellaneous Prelims 2007
Ortho and Para nitrophenols can be separated by
A. Crystallization
B. Steam distillation
C. Sublimation
D. Filtration
Explanation
Why Correct: Ortho-nitrophenol has intramolecular H-bonding and is steam volatile, while para-nitrophenol has intermolecular H-bonding and is not steam volatile; steam distillation separates them.
Distractor Analysis: Crystallization exploits solubility differences; sublimation requires direct solid-to-vapor transition; filtration separates solids from liquids — none apply to this mixture.
Takeaway: Intramolecular H-bonding reduces intermolecular forces, making the compound more volatile and separable by steam distillation.
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Q.16
WBPSC Miscellaneous Prelims 2007
When passed over copper at 300°C, ethyl alcohol vapour forms
A. C2H4
B. CH3CHO
C. CH3COCH3
D. C2H6
Explanation
Why Correct: Ethanol (C2H5OH) undergoes dehydrogenation over copper catalyst at 300°C to form acetaldehyde (CH3CHO) and hydrogen gas.
Distractor Analysis: C2H4 (ethene) is formed by dehydration of ethanol with concentrated H2SO4 at 170°C, not with copper. C2H6 (ethane) is formed by reduction or hydrogenation, not from ethanol vapor over copper. CH3COCH3 (acetone) is typically produced from isopropyl alcohol, not ethanol.
Takeaway: Copper at 300°C is a classic dehydrogenation catalyst; ethanol gives acetaldehyde, while propan-2-ol gives acetone under similar conditions.
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Q.17
WBPSC Miscellaneous Prelims 2007
The alkaloid found in Cinchona is
A. Reserpine
B. Nicotine
C. Morphine
D. Quinine
Explanation
Why Correct: Cinchona bark contains quinine, an alkaloid used historically as an antimalarial drug.
Distractor Analysis: Reserpine is an alkaloid from Rauwolfia serpentina used as an antihypertensive. Nicotine is an alkaloid from tobacco. Morphine is an alkaloid from opium poppy.
Takeaway: Alkaloids are nitrogenous organic compounds from plants with pharmacological effects. Quinine from Cinchona is a classic antimalarial.
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Q.18
WBPSC Miscellaneous Prelims 2007
Benzyl Chloride is hydrolysed by sodium hydroxide solution to form
A. Benzoic acid
B. Benzaldehyde
C. Benzyl alcohol
D. Benzoin
Explanation
Why Correct: Benzyl chloride (C6H5CH2Cl) undergoes nucleophilic substitution with aqueous NaOH. The chlorine is replaced by hydroxyl (-OH) group, yielding benzyl alcohol (C6H5CH2OH).
Distractor Analysis: Benzoic acid (C6H5COOH) requires oxidation of benzyl alcohol or alkyl benzene. Benzaldehyde (C6H5CHO) is an aldehyde, obtained by partial oxidation of benzyl alcohol. Benzoin (C6H5CH(OH)COC6H5) is a hydroxyketone formed from benzaldehyde via condensation; none of these are direct hydrolysis products of benzyl chloride.
Takeaway: Hydrolysis of alkyl halides with aqueous alkali gives alcohols. Benzyl chloride is a primary halide forming primary alcohol. Stronger oxidizing conditions convert benzyl alcohol to benzaldehyde then to benzoic acid.
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Q.19
WBPSC Miscellaneous Prelims 2007
The number of chiral carbons present in tartaric acid is
A. 2
B. 4
C. 3
D. 1
Explanation
Why Correct: Tartaric acid has two chiral carbons at positions 2 and 3, each bonded to four different groups. Although there are two chiral centers, the molecule is meso due to internal compensation, but the number of chiral carbons remains two.
Distractor Analysis: 4 corresponds to the total number of stereoisomers possible for a compound with two chiral centers under certain conditions, not the count of chiral carbons. 3 is not possible for a simple tartaric acid structure; it would require an odd number of chiral centers. 1 would imply only one asymmetric carbon, which would yield enantiomers, but tartaric acid has two.
Takeaway: Always count chiral carbons as those bonded to four different substituents; tartaric acid is a classic example of a meso compound with two chiral carbons yet optically inactive.
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Q.20
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
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 the other listed structures.
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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