Practice MCQs for JEE Chemistry Hydrocarbons
Access targeted multiple-choice questions for Hydrocarbons designed to align with the latest JEE academic syllabus for JEE Chemistry. These objective practice sets help students evaluate their conceptual understanding and improve exam readiness.
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Multiple Choice Questions
(a) halogenation
(b) nitration
(c) sulphonation
(d) oxidation
Show Answer & Explanation
Answer: (d) oxidation
Explanation:
1. Benzene is aromatic and resists oxidation; the ring is not oxidised by common oxidants such as KMnO4.
2. It readily undergoes electrophilic substitutions such as halogenation, nitration and sulphonation, which keep the aromatic sextet.
Teacher's Note:
1. Aromatic stability makes the ring resist addition and oxidation.
(a) CH3CH=CH2 + HBr in the presence of R2O2 giving CH3CH2CH2Br
(b) CH2=CH2 + HBr giving CH3CH2Br in the dark
(c) CH3CH=CH2 + HCl giving CH3CHClCH3
(d) CH3CH=CH2 + HOBr giving CH3CH(OH)CH2Br
Show Answer & Explanation
Answer: (a) CH3CH=CH2 + HBr in the presence of R2O2 giving CH3CH2CH2Br
Explanation:
1. Peroxides produce Br· from HBr, so the addition is a radical chain (the peroxide effect) and gives the anti-Markovnikov product.
2. The other additions are polar electrophilic additions.
Teacher's Note:
1. Peroxide plus HBr: radical addition.
2. HCl and HI do not show the peroxide effect.
(a) a meso dibromide
(b) an optically active single enantiomer
(c) a mixture of diastereomeric dibromides
(d) a racemic dibromide
Show Answer & Explanation
Answer: (d) a racemic dibromide
Explanation:
1. Br2 adds anti through a bromonium ion. Anti addition to a cis alkene gives the (3R,4R) and (3S,4S) 3,4-dibromohexanes in equal amounts.
2. Equal amounts of enantiomers make a racemic mixture (the trans alkene would give the meso compound).
Teacher's Note:
1. cis + anti addition: racemic.
2. trans + anti addition: meso.
(a) 2-chlorobutane
(b) 1-chlorobutane
(c) 1,2-dichlorobutane
(d) 2,2-dichlorobutane
Show Answer & Explanation
Answer: (a) 2-chlorobutane
Explanation:
1. Chlorine is only mildly selective: the secondary C-H is about 3.8 times as reactive as the primary C-H, and there are 4 secondary and 6 primary hydrogens.
2. Relative yield: secondary 4 x 3.8 = 15.2, primary 6 x 1 = 6, so about 72 percent 2-chlorobutane.
Teacher's Note:
1. Rate = number of hydrogens x reactivity per hydrogen.
(a) a free radical mechanism
(b) an ionic mechanism
(c) heterolytic fission of the double bond
(d) a carbocation mechanism
Show Answer & Explanation
Answer: (a) a free radical mechanism
Explanation:
1. Peroxides decompose into radicals, which generate Br· from HBr.
2. A chain of radical steps follows: Br· adds to the alkene and the resulting radical abstracts H from HBr.
Teacher's Note:
1. Peroxide means radicals.
(a) 16/31
(b) 6/31
(c) 3/31
(d) 9/31
Show Answer & Explanation
Answer: (b) 6/31
Explanation:
1. 3-Methylpentane has 1 tertiary H (reactivity 6), 4 secondary H (4 x 4 = 16), 6 primary H on the two ethyl CH3 groups (6 x 1 = 6) and 3 primary H on the methyl group (3 x 1 = 3).
2. Total = 6 + 16 + 6 + 3 = 31. 3-Chloro-3-methylpentane comes from the tertiary H: 6/31.
Teacher's Note:
1. Rate share = (number of H x reactivity) / total.
(a) CH3 > OH > NO2 > Cl
(b) OH > CH3 > Cl > NO2
(c) OH > Cl > CH3 > NO2
(d) OH > CH3 > NO2 > Cl
Show Answer & Explanation
Answer: (b) OH > CH3 > Cl > NO2
Explanation:
1. -OH is a strong activator (+M), CH3 a weak activator (+I and hyperconjugation).
2. Chlorine deactivates mildly (-I > +M), and NO2 deactivates strongly (-I and -M), so nitrobenzene reacts slowest.
Teacher's Note:
1. Strong activator > weak activator > halogen > strong deactivator.
(a) nucleophilic substitution
(b) electrophilic substitution
(c) electrophilic addition
(d) free radical substitution
Show Answer & Explanation
Answer: (d) free radical substitution
Explanation:
1. NBS provides a very low concentration of Br2; light or peroxide gives Br·, which abstracts an allylic hydrogen to form a resonance-stabilised allyl radical.
2. The allyl radical takes Br from Br2; one H is replaced by Br in a radical chain: free radical substitution.
Teacher's Note:
1. Low Br2 concentration prevents addition to the double bond.
(a) base
(b) acid
(c) reducing agent
(d) catalyst
Show Answer & Explanation
Answer: (a) base
Explanation:
1. The stronger acid H2SO4 protonates HNO3 to H2NO3+, which loses water to give the nitronium ion NO2+.
2. In this step HNO3 accepts a proton, so it behaves as a base, and H2SO4 is the acid.
Teacher's Note:
1. Who gives the proton and who takes it?
2. H2SO4 is the stronger acid.
(a) CH2=CH2
(b) CH3CH=CH2
(c) (CH3)2C=CH-CH3
(d) CH3CH=CHCH3
Show Answer & Explanation
Answer: (c) (CH3)2C=CH-CH3
Explanation:
1. Electrophilic addition is faster when the double bond carries more electron-releasing alkyl groups, which stabilise the bromonium ion or carbocation.
2. 2-Methylbut-2-ene is trisubstituted, so it is the most reactive.
Teacher's Note:
1. More substituted C=C means more reactive towards electrophiles.
(a) nitrobenzene
(b) phenol
(c) quinol (hydroquinone)
(d) m-dinitrobenzene
Show Answer & Explanation
Answer: (d) m-dinitrobenzene
Explanation:
1. Two nitro groups strongly deactivate the ring (-I, -M), more than one.
2. Phenol and quinol have activating OH groups, and nitrobenzene has only one deactivating group.
Teacher's Note:
1. Count the deactivating groups.
(a) benzyl chloride
(b) m-chlorotoluene
(c) o- and p-chlorotoluene
(d) benzal chloride
Show Answer & Explanation
Answer: (c) o- and p-chlorotoluene
Explanation:
1. FeCl3 is a Lewis acid that generates the electrophile Cl+, so the ring is substituted (electrophilic substitution).
2. The methyl group activates and directs to the ortho and para positions. Side-chain chlorination (benzyl chloride, benzal chloride) needs light or heat.
Teacher's Note:
1. Lewis acid: ring substitution.
2. Light: side-chain substitution.
(a) 1-bromo-2-methylcyclohexane
(b) 1-bromo-1-methylcyclohexane
(c) 3-bromo-1-methylcyclohexene
(d) 6-bromo-1-methylcyclohexene
Show Answer & Explanation
Answer: (b) 1-bromo-1-methylcyclohexane
Explanation:
1. H+ adds to C-2 so that the tertiary carbocation forms at C-1.
2. Bromide adds to C-1: Markovnikov product, 1-bromo-1-methylcyclohexane.
Teacher's Note:
1. Tertiary carbocation is the most stable.
(a) benzene but not nitrobenzene
(b) both benzene and nitrobenzene
(c) neither of them
(d) nitrobenzene but not benzene
Show Answer & Explanation
Answer: (d) nitrobenzene but not benzene
Explanation:
1. Benzene would itself be alkylated or acylated.
2. Nitrobenzene is strongly deactivated and does not undergo Friedel-Crafts reactions, so it is an inert solvent.
Teacher's Note:
1. A solvent must not react under the conditions.
(a) They are mostly deactivating groups
(b) They are mostly activating groups
(c) They are mostly neutral groups
(d) They are never activating
Show Answer & Explanation
Answer: (b) They are mostly activating groups
Explanation:
1. Groups with lone pairs or alkyl groups donate electrons and direct ortho-para while activating the ring.
2. The halogens are the main exception: deactivating but ortho-para directing.
Teacher's Note:
1. +M and +I groups activate.
(a) chlorobenzene
(b) phenol
(c) but-2-yne
(d) pent-1-ene
Show Answer & Explanation
Answer: (a) chlorobenzene
Explanation:
1. Alkenes and alkynes add Br2 readily, and phenol is brominated rapidly because OH activates the ring.
2. Chlorobenzene is deactivated and needs a Lewis acid catalyst.
Teacher's Note:
1. Benzene derivatives need FeBr3 unless strongly activated.
(a) 1-chloro-1-phenylpropane
(b) 3-chloro-1-phenylpropane
(c) 2-chloro-1-phenylpropane
(d) 4-chloropropylbenzene
Show Answer & Explanation
Answer: (a) 1-chloro-1-phenylpropane
Explanation:
1. Under light the reaction is a radical substitution on the side chain.
2. The benzylic hydrogen gives the benzylic radical, stabilised by resonance with the ring, so substitution occurs at the carbon next to the ring.
Teacher's Note:
1. Benzylic radical is the most stable.
(a) 2-bromobutane
(b) 1-bromobut-1-ene
(c) 1-bromobutane
(d) 2-bromobut-2-ene
Show Answer & Explanation
Answer: (c) 1-bromobutane
Explanation:
1. Peroxide gives Br· which adds to the terminal carbon to produce the more stable secondary radical.
2. The radical abstracts H from HBr: anti-Markovnikov product CH3CH2CH2CH2Br.
Teacher's Note:
1. Peroxide effect applies only to HBr.
(a) I > II > III
(b) III > I > II
(c) the rate is the same for all three
(d) II > I > III
Show Answer & Explanation
Answer: (c) the rate is the same for all three
Explanation:
1. In electrophilic substitution the rate-determining step is attack of the electrophile on the ring (formation of the sigma complex).
2. C-H or C-D bond breaking occurs in the fast second step, so there is no kinetic isotope effect.
Teacher's Note:
1. No isotope effect when the C-H cleavage is not rate determining.
(a) 2-bromopropan-1-ol
(b) 3-bromopropan-1-ol
(c) 2-bromopropan-2-ol
(d) 1-bromopropan-2-ol
Show Answer & Explanation
Answer: (d) 1-bromopropan-2-ol
Explanation:
1. Br+ adds to the terminal carbon, giving the bromonium ion or the secondary carbocation.
2. Water attacks the more substituted carbon, so OH ends on C-2: CH3CH(OH)CH2Br.
Teacher's Note:
1. Halohydrin formation: halogen on the less substituted carbon, OH on the more substituted carbon.
(a) a catalytic amount
(b) exactly 0.1 equivalent
(c) more than one equivalent
(d) any amount; it does not matter
Show Answer & Explanation
Answer: (c) more than one equivalent
Explanation:
1. The product ketone is a Lewis base and forms a stable complex with AlCl3, which therefore is not free to act as a catalyst.
2. So at least one equivalent (usually a slight excess) is needed.
Teacher's Note:
1. The ketone product complexes the Lewis acid.
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Multiple Choice Questions (MCQs) for JEE Chemistry Hydrocarbons
JEE Chemistry Hydrocarbons Objective Test Questions
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FAQs
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