All questions of Hydrocarbons for JEE Exam

Which of the following compounds does not dissolve in conc. H2SO4 even on warming? (1983 - 1 Mark)
  • a)
    ethylene
  • b)
    benzene
  • c)
    hexane
  • d)
    aniline
Correct answer is option 'C'. Can you explain this answer?

Advait Singh answered
CH2 = CH2 + H2SO4 → CH3CH2OSO3H
C6H6 + H2SO4 → C6H5SO3H + H2O
C6H14 + H2SO4 → No reaction
Only hexane does not dissolve in conc. H2SO4 even on warming.

Which compound would give 5 - keto - 2 - methylhexanal upon ozonolysis ?        [JEE M 2015]
  • a)
  • b)
  • c)
  • d)
Correct answer is option 'D'. Can you explain this answer?

Chirag Verma answered
When 1, 3-dimethylcyclopentene is heated with ozone and then with zinc and acetic acid, oxidative cleavage leads to keto - aldehyde.
5- keto – 2 – methylhexanal

Identify the product, P in the following reaction : CH3 - CH = CH2 + NOCl —→ P (2006 - 3M, –1)
  • a)
  • b)
  • c)
  • d)
Correct answer is option 'B'. Can you explain this answer?

Ananya Das answered
Nitrosyl chloride adds on olefins accor ding to Markovnikof’s rule, where NO+ constitutes the positive part of the addendum.

On monochlorination of 2-methylbutane, the total number of chiral compounds formed is (2004S)
  • a)
    2
  • b)
    4
  • c)
    6
  • d)
    8
Correct answer is option 'B'. Can you explain this answer?

Rohit Jain answered
                                                   
(i) Chlorination at C-2 and C-4 produces no chiral compounds
(ii) Chlorination at C-3 produces a chiral carbon marked with star (d and l form).
(iii) Chlorination at C-1 also produces a chiral carbon marked with star (d and l form).

N(isomeric products) ; C5H11Cl
(isomeric products) Identify N and M (2006 - 5M,)
Identify N and M (2006 - 5M, –1)
  • a)
    6, 4
  • b)
    6, 6
  • c)
    4, 4
  • d)
    3, 3
Correct answer is option 'A'. Can you explain this answer?

Geetika Shah answered
So, the value of N will be 1 + 2 + 2 + 1 = 6.
Since enantiomers have nearly same physical properties, II and III as well as IV and V can’t be separated, hence the number of isomers (M) will be 1 + 1 + 1 + 1 = 4.

2-Hexyne gives trans-2-Hexene on treatment with :
  • a)
    Pt/H2
  • b)
    Li / NH3 [2012]
  • c)
    Pd/BaSO4
  • d)
    Li AlH4
Correct answer is option 'B'. Can you explain this answer?

Yash Modi answered
It's B, which is the process of Birch Reduction where trans form of Alkene is formed. cis form is formed on reaction with H2+ Lindlar's catalyst.

The bond energy (in kcal mol–1) of a C–C single bond is approximately (2010)
  • a)
    1
  • b)
    10
  • c)
    100
  • d)
    1000
Correct answer is option 'C'. Can you explain this answer?

Neer Shreyansh answered
•The bond energy (in kcal/mol) of C-C single bond is approximately 100Kcal/mol.________________________________ •Explanation:___________________________ •Bond Energy is an important concept while dealing with the Chemical Compound.__________________________ •Bond Energy is also known by the name 'bond Enthalpy'._______________________ •It is used to describe the strength of the bond in a chemical compound.________ •Bond Energy can be defined as the energy needed to dissociate a bond in a chemical compound.______________________________ •These values are determined through experiments on various chemical compounds._____________________________________ •It can take '100 kcal of energy' to break' 1 mol of C–H bonds'._____________________ That's all

Which types of isomerism is shown by 2, 3-dichlorobutane? [2005]
  • a)
    Structural
  • b)
    Geometric
  • c)
    Optical
  • d)
    Diastereo
Correct answer is option 'C'. Can you explain this answer?

Jyoti Patel answered
Explanation:
2,3-dichlorobutane has the chemical formula C4H8Cl2. It contains a chain of four carbon atoms with two chlorine atoms attached to the second and third carbon atoms. This compound exhibits different types of isomerism.

Structural Isomerism:
Structural isomerism refers to the isomers that have the same molecular formula but differ in the arrangement of atoms within the molecule. In the case of 2,3-dichlorobutane, it does not exhibit structural isomerism because there is only one way to arrange the carbon atoms and chlorine atoms in the molecule.

Geometric Isomerism:
Geometric isomerism occurs when two or more isomers have the same connectivity of atoms but differ in the spatial arrangement of atoms due to restricted rotation around a double bond or a ring. Since 2,3-dichlorobutane does not contain any double bonds or rings, it does not exhibit geometric isomerism.

Optical Isomerism:
Optical isomerism, also known as enantiomerism, occurs when a compound is chiral and has non-superimposable mirror images. Chirality arises when a carbon atom is bonded to four different groups. In 2,3-dichlorobutane, there is no carbon atom with four different groups, so it does not exhibit optical isomerism.

Diastereomerism:
Diastereomerism occurs when two or more isomers have the same connectivity of atoms but differ in their spatial arrangement, and they are not mirror images of each other. In the case of 2,3-dichlorobutane, it does not exhibit diastereomerism because there is no other isomer with the same molecular formula but different spatial arrangement.

Therefore, the correct type of isomerism exhibited by 2,3-dichlorobutane is Optical Isomerism (Enantiomerism).

Which of the following will have least hindered rotation about carbon-carbon bond? (1987 - 1 Mark)
  • a)
    Ethane
  • b)
    Ethylene
  • c)
    Acetylen e
  • d)
    Hexachloroethane
Correct answer is option 'A'. Can you explain this answer?

Ruchi Tiwari answered
Ethylene has restricted rotation [due to C = C], acetylene no rotation [due to C ≡ C], hexachloroethane has more rotation than ethylene but less than ethane because of greater size of the substituent (chlorine) than in ethane (substituent is hydrogen).

Acidic hydrogen is present in : (1985 - 1 Mark)
  • a)
    ethyne
  • b)
    ethene
  • c)
    benzene
  • d)
    ethane
Correct answer is option 'A'. Can you explain this answer?

Ananya Das answered
Acidic hydrogen is present in alkynes, attached to the triply bonded C-atoms. They can be easily removed by means of a strong base.

The nodal plane in the π-bond of ethene is located in
  • a)
    the molecular plane (2002S)
  • b)
    a plane parallel to the molecular plane
  • c)
    a plane perpendicular to the molecular plane which bisects the carbon - carbon σ -bond at right angle
  • d)
    a plane perpendicular to the molecular plane which contains the carbon - carbon σ -bond.
Correct answer is option 'A'. Can you explain this answer?

TIPS/Formulae : The π bond is formed by the sideways overlapping of two p-orbitals of the two carbon atoms.
The molecular plane does not have any π electron density as the p-orbitals are perpendicular to the plane containing the ethene molecule. The nodal plane in the π-bond of ethene is located in the molecular plane.

Identify the reagent from the following list which can easily distinguish between 1-butyne and 2-butyne (2002S)
  • a)
    bromine, CCl4
  • b)
    H2, Lindlar catalyst
  • c)
    dilute H2SO4, HgSO4
  • d)
    ammonical Cu2Cl2 solution
Correct answer is option 'D'. Can you explain this answer?

Lavanya Menon answered
TIPS/Formulae : In 1-butyne terminal hydrogen is acidic where as in 2-butyne there is no terminal hydrogen. Thus 2-butyne will not react with ammonical Cu2Cl2. While 1-butyne, being terminal alkyne, will give red ppt. with ammonical cuprous chloride

The compound formed as a result of oxidation of ethyl benzene by KMnO4 is [2007]
  • a)
    benzyl alcohol
  • b)
    benzophenone
  • c)
    acetophenone
  • d)
    benzoic acid.
Correct answer is option 'D'. Can you explain this answer?

Vaibhav Datta answered
When alkyl benzene are oxidised with alkaline KMnO4, (strong oxidising agent) the entire alkyl group is oxidised to –COOH group regardless of length of side chain.

Among P, Q, R and S, the aromatic compound(s) is/are (JEE Advanced 2013-I)
  • a)
    P
  • b)
    R
  • c)
    Q
  • d)
    S
Correct answer is option 'A,B,C,D'. Can you explain this answer?

Geetika Shah answered
                                                                      
Note : P has 2 p electrons, while Q, R & S have 6 p electrons each. Hence all the 4 are aromatic.

The reaction of toluene with Cl2 in presence of FeCl3 gives predominantly [2007]
  • a)
    m-chlorobenzene
  • b)
    benzoyl chloride
  • c)
    benzyl chloride
  • d)
    o- and p-chlorotoluene.
Correct answer is option 'D'. Can you explain this answer?

Yash Modi answered
The CH3 group in toluene shows both +I and Hyperconjugation effects which activate the Benzene ring. Thus -ve charge density increases (at the o- and p- positions). Now, the above reaction includes halogenation of Benzene which is an example of electrophilic aromatic substitution reaction. FeCl3 acts as a Lewis acid and takes Cl from Cl2 forming FeCl4- and Cl+. The latter being an electrophile attacks the ring at the o- and p- positions to form the respective products.

Acid catalyzed hydration of alkenes except ethene leads to the formation of
  • a)
    mixture of secondary and tertiary alcohols
  • b)
    mixture of primary and secondary alcohols
  • c)
    secondary or tertiary alcohol
  • d)
    primary alcohol
Correct answer is option 'A'. Can you explain this answer?

Naveen Goyal answered
Water adds directly to the more reactive alkene in presence of a  strongly acidic catalyst forming alcohols.
Addition occurs according to Markonikov’s rule.
NOTE : Addition follows Markownikoff’s rule.

Which one of the following will react fastest with H2 under catalytic hydrogenation condition ? (2000S)
  • a)
  • b)
  • c)
  • d)
Correct answer is option 'A'. Can you explain this answer?

Palak Datta answered
TIPS/Formulae : The relative rates of hydrogenation decreases with increase of steric hinderance.
R2C = CH2 > RCH = CHR > R2C = CHR > R2C = CR2
Among the four olefins, (a) and (b) are less stable (Saytzeff  rule). Further in (a), the  bulky alkyl groups are on same side (cis-isomer), hence it is less stable.

(2003S)
  • a)
  • b)
  • c)
  • d)
Correct answer is option 'A'. Can you explain this answer?

Yash Modi answered
Carbocation will be formed in the Phenyl position (1st C outside ring). That will be resonance stabilized. The water will attack there, forming an -enol. This will tautomerise to form the corresponding ketone. That will be A.

Consider the following reaction (2002S)
Identify the structure of the major product 'X'
  • a)
  • b)
  • c)
  • d)
Correct answer is option 'B'. Can you explain this answer?

Akshay Chauhan answered
Br is less reactive and more selective and so the most stable free radical (3°) will be the major product.

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