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JEE Chemistry
Organic Chemistry

Chemistry questions for JEE Main — Physical, Organic, Inorganic Chemistry.

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Topics in JEE Chemistry
Which intermediate is formed when acetyl chloride reacts with benzene in the presence of AlCl₃?
A Acetyl cation (CH₃CO⁺)
B Phenyl carbocation
C Chlorobenzene adduct
D Aluminum-chlorine complex
Correct Answer:  A. Acetyl cation (CH₃CO⁺)
EXPLANATION

In Friedel-Crafts acylation, AlCl₃ facilitates the formation of the acetyl cation (CH₃CO⁺) from acetyl chloride. This electrophilic acylium ion then attacks the benzene ring.

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Q.2 Medium Organic Chemistry
In the nitration of benzene with HNO₃/H₂SO₄, the rate-determining step involves attack by:
A NO₂⁺ (nitronium ion)
B NO₂• (nitrogen dioxide radical)
C HNO₃ (nitric acid molecule)
D NO₃⁻ (nitrate ion)
Correct Answer:  A. NO₂⁺ (nitronium ion)
EXPLANATION

The HNO₃/H₂SO₄ mixture generates NO₂⁺ (nitronium ion), which is the electrophile attacking the benzene ring in the rate-determining step. This is a classic electrophilic aromatic substitution.

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Which of the following is the correct IUPAC name for the compound CH₃-CHBr-CH₂-CH₃?
A 2-bromobutane
B 1-bromobutane
C 3-bromobutane
D sec-butyl bromide
Correct Answer:  A. 2-bromobutane
EXPLANATION

The parent chain is butane (4 carbons). Numbering from the end nearest to substituent gives Br at position 2. IUPAC name is 2-bromobutane. Option D is a common name.

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Q.4 Medium Organic Chemistry
The addition of HBr to propene in the presence of peroxides follows:
A Markovnikov's rule to give 2-bromopropane
B Anti-Markovnikov's rule to give 1-bromopropane
C Free radical mechanism to give equal amounts of both isomers
D Ionic mechanism to give 2-bromopropane
Correct Answer:  B. Anti-Markovnikov's rule to give 1-bromopropane
EXPLANATION

Peroxides initiate free radical mechanism (Kharasch effect). In free radical addition, HBr adds anti-Markovnikov to propene, giving 1-bromopropane as the major product. The Br radical adds first to the terminal carbon.

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Q.5 Medium Organic Chemistry
In the dehydration of 2-methylbutan-2-ol, the major product is:
A 2-methylbut-1-ene
B 2-methylbut-2-ene
C But-1-ene
D Pent-2-ene
Correct Answer:  B. 2-methylbut-2-ene
EXPLANATION

Dehydration of 2-methylbutan-2-ol follows Zaitsev's rule, producing the most stable (most substituted) alkene. 2-methylbut-2-ene is a trisubstituted alkene and is the major product.

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Which of the following compounds will give a positive Tollens test?
A Acetone
B Propanal
C Diethyl ether
D tert-butanol
Correct Answer:  B. Propanal
EXPLANATION

Tollens test is positive for aldehydes. Propanal (CH₃CH₂CHO) is an aldehyde and gets oxidized to carboxylic acid, reducing Ag⁺ to Ag (silver mirror). Acetone is a ketone, ether and alcohol do not give positive test.

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Q.7 Medium Organic Chemistry
The reaction of phenol with excess bromine in water produces:
A 2,4,6-tribromophenol
B 4-bromophenol
C 2,4-dibromophenol
D 2,6-dibromophenol
Correct Answer:  A. 2,4,6-tribromophenol
EXPLANATION

Phenol is highly activated towards electrophilic aromatic substitution due to the electron-donating -OH group. Bromine can add at all three ortho and para positions with excess bromine, giving 2,4,6-tribromophenol.

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Which mechanism is involved in the reaction of tert-butyl bromide with aqueous NaOH?
A SN1
B SN2
C E1
D E2
Correct Answer:  A. SN1
EXPLANATION

tert-Butyl bromide is a tertiary alkyl halide. Tertiary substrates preferentially undergo SN1 mechanism due to stable tertiary carbocation formation. SN2 is hindered by steric effects.

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In the ozonolysis of but-2-ene, the products formed are:
A 2 moles of acetaldehyde
B 1 mole of formaldehyde and 1 mole of acetaldehyde
C 2 moles of formaldehyde
D propanal and methanol
Correct Answer:  A. 2 moles of acetaldehyde
EXPLANATION

But-2-ene (CH₃-CH=CH-CH₃) on ozonolysis gives two identical fragments, each being acetaldehyde (CH₃CHO). The double bond cleaves symmetrically.

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Q.10 Medium Organic Chemistry
Which of the following alkenes will undergo hydroboration-oxidation to give a secondary alcohol as the major product?
A 1-methylcyclohexene
B 2-methylbut-2-ene
C pent-1-ene
D 2,3-dimethylbut-2-ene
Correct Answer:  A. 1-methylcyclohexene
EXPLANATION

Hydroboration-oxidation follows anti-Markovnikov's rule and gives Markovnikov's hydration product after oxidation. 1-methylcyclohexene gives secondary alcohol, while pent-1-ene gives primary and 2-methylbut-2-ene gives tertiary alcohol.

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