JEE Chemistry — Organic Chemistry
Chemistry questions for JEE Main — Physical, Organic, Inorganic Chemistry.
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Showing 1–10 of 49 questions in Organic Chemistry
Q.1 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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Q.2 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.3 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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Q.4 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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Q.5 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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Q.6 Medium Organic Chemistry
The compound that will show maximum hydrogen bonding is:
A CH3-CH2-OH
B CH3-CO-NH2
C CH3-CH2-NH2
D CH3-CHO
Correct Answer:  B. CH3-CO-NH2
EXPLANATION

Amides have both N-H (hydrogen bond donor) and C=O (hydrogen bond acceptor), allowing formation of strong intermolecular hydrogen bonds.

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Q.7 Medium Organic Chemistry
The major product when 2-methylbut-3-en-1-ol undergoes PCC oxidation is:
A 2-methylbut-3-en-1-aldehyde
B 2-methylbut-3-enoic acid
C 2-methylbut-3-en-1-one
D 2-methylbutyric acid
Correct Answer:  A. 2-methylbut-3-en-1-aldehyde
EXPLANATION

PCC (Pyridinium chlorochromate) selectively oxidizes primary alcohols to aldehydes without further oxidation, and doesn't affect C=C.

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Q.8 Medium Organic Chemistry
In the Clemmensen reduction of a ketone, the reducing agent used is:
A Zn(Hg) and conc. HCl
B LiAlH4
C NaBH4
D H2 with Pd-C
Correct Answer:  A. Zn(Hg) and conc. HCl
EXPLANATION

Clemmensen reduction uses zinc amalgam with concentrated HCl to convert C=O to CH2, unlike Wolff-Kishner which uses hydrazine.

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Q.9 Medium Organic Chemistry
In the reaction of phenylmagnesium bromide (Grignard reagent) with CO2 followed by hydrolysis, the main product is:
A Benzene
B Benzoic acid
C Phenol
D Benzaldehyde
Correct Answer:  B. Benzoic acid
EXPLANATION

Grignard reagent attacks CO2 to form a salt, which upon hydrolysis gives benzoic acid.

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Q.10 Medium Organic Chemistry
The reaction of acetyl chloride with aniline preferentially gives N-acetylaniline rather than p-acetylaniline because:
A Nitrogen is more nucleophilic than benzene ring
B Acetyl chloride reacts with acyl group
C The product is kinetically favored
D Aniline acts as an electrophile
Correct Answer:  A. Nitrogen is more nucleophilic than benzene ring
EXPLANATION

The lone pair on nitrogen of aniline is more nucleophilic than the π electrons of benzene, making N-acylation the dominant pathway.

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