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JEE Chemistry
Organic Chemistry

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

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Difficulty: All Easy Medium Hard 21–30 of 100
Topics in JEE Chemistry
Q.21 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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Q.22 Medium Organic Chemistry
In the nitration of anisole (C6H5-O-CH3), the major product is:
A 2-nitroanisole
B 3-nitroanisole
C 4-nitroanisole
D 2,4-dinitroanisole
Correct Answer:  A. 2-nitroanisole
EXPLANATION

Methoxy group is ortho-para directing and activating. Due to steric hindrance at para position, 2-nitroanisole is the major product.

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Which mechanism best describes the addition of HBr to propene?
A SN1
B SN2
C Electrophilic addition
D Free radical addition
Correct Answer:  C. Electrophilic addition
EXPLANATION

Addition to alkenes follows electrophilic addition mechanism with carbocation formation, leading to Markovnikov's product.

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The oxidation of primary alcohols with chromic acid (H2CrO4) in acidic medium gives:
A Aldehydes
B Ketones
C Carboxylic acids
D Esters
Correct Answer:  C. Carboxylic acids
EXPLANATION

Chromic acid oxidizes primary alcohols to carboxylic acids. The aldehyde is an intermediate which is further oxidized.

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In the bromination of toluene, the ortho:para ratio is approximately 2:1 instead of 1:1 due to:
A Steric hindrance at ortho position
B Thermodynamic stability of para isomer
C Kinetic control with partial steric effects
D Electronic effects favoring para position
Correct Answer:  C. Kinetic control with partial steric effects
EXPLANATION

Although para is thermodynamically more stable, ortho is kinetically favored but sterically hindered. The 2:1 ratio reflects kinetic control with steric factors reducing ortho product.

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Q.26 Medium Organic Chemistry
Which of the following compounds will not give a positive Iodoform test?
A CH3-CH2-CH(OH)-CH3
B CH3-CO-CH3
C C6H5-CH2-CH(OH)-CH3
D CH3-CH2-OH
Correct Answer:  D. CH3-CH2-OH
EXPLANATION

Iodoform test requires either a methyl ketone (COCH3) or secondary alcohol with CH3 adjacent to CHOH. Ethanol has no such structure.

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Q.27 Medium Organic Chemistry
The pKa of phenol (C6H5OH) is approximately 10, while that of aliphatic alcohol is around 16. This difference is due to:
A Greater electronegativity of aromatic carbon
B Resonance stabilization of phenoxide ion through benzene ring
C Inductive effect of benzene ring
D Hydrogen bonding in phenol
Correct Answer:  B. Resonance stabilization of phenoxide ion through benzene ring
EXPLANATION

Phenoxide ion is stabilized by resonance with the benzene ring, making phenol more acidic than aliphatic alcohols.

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Which reagent is used to differentiate between aldehydes and ketones?
A Tollens reagent
B Fehling reagent
C Both A and B
D Bromine water
Correct Answer:  C. Both A and B
EXPLANATION

Both Tollens and Fehling reagents give positive test with aldehydes (silver mirror and red precipitate respectively) but not with ketones.

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Q.29 Medium Organic Chemistry
In the Friedel-Crafts alkylation of benzene with 1-chloropropane and AlCl3, the major product is isopropylbenzene due to:
A Formation of secondary carbocation which rearranges to tertiary
B Direct formation of tertiary carbocation
C SN2 mechanism preference
D Formation of primary carbocation
Correct Answer:  A. Formation of secondary carbocation which rearranges to tertiary
EXPLANATION

Primary carbocation rearranges via hydride shift to form more stable secondary carbocation, which then forms isopropylbenzene.

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Which of the following compounds undergoes SN1 reaction most readily?
A (CH3)3C-Br
B CH3-CH2-Br
C (CH3)2CH-Br
D CH3-Br
Correct Answer:  A. (CH3)3C-Br
EXPLANATION

Tertiary alkyl halides form stable tertiary carbocations, making SN1 mechanism favorable.

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