JEE Chemistry Organic Chemistry Some Basic Principles and Techniques MCQs Set 35

Multiple Choice Questions (MCQs) for JEE Chemistry: Organic Chemistry Some Basic Principles and Techniques

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Practice Organic Chemistry Some Basic Principles and Techniques MCQs for JEE Chemistry

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Multiple Choice Questions

Question 1: The IUPAC name of \( \ce{CH3-CHBr-CH2OH} \) is
(a) 3-Hydroxy-2-bromopropane
(b) 2-Bromopropan-1-ol
(c) 2-Bromo-3-propanol
(d) 3-Hydroxyisopropyl bromide
Show Answer & Explanation

Answer: (b) 2-Bromopropan-1-ol

Explanation:
1. The OH group is the principal group and gets the lowest locant, so the chain is numbered from the \( \ce{CH2OH} \) carbon
2. Br is on C-2, giving 2-bromopropan-1-ol

Teacher's Note:
1. Find the principal functional group first, then the longest chain containing it, then number for the lowest locants.
2. Write substituent prefixes in alphabetical order.

Question 2: The IUPAC name of \( \ce{CH3CHO} \) is
(a) Acetaldehyde
(b) Methyl aldehyde
(c) Ethanol
(d) Ethanal
Show Answer & Explanation

Answer: (d) Ethanal

Explanation:
1. The two-carbon aldehyde takes the suffix -al
2. Ethane minus e plus al gives ethanal (acetaldehyde is the common name)

Teacher's Note:
1. Eliminate options with an incorrect parent chain length first.
2. Then compare locants and alphabetical order among the remaining options.

Question 3: The IUPAC name of \( \ce{CH3CH(OH)CH2CH2COOH} \) is
(a) 4-Hydroxypentanoic acid
(b) 1-Carboxy-3-butanoic acid
(c) 1-Carboxy-4-butanol
(d) 4-Carboxy-2-butanol
Show Answer & Explanation

Answer: (a) 4-Hydroxypentanoic acid

Explanation:
1. COOH is the principal group, so C-1 is the carboxyl carbon and the chain has five carbons
2. OH is on C-4, giving 4-hydroxypentanoic acid

Teacher's Note:
1. Find the principal functional group first, then the longest chain containing it, then number for the lowest locants.
2. Write substituent prefixes in alphabetical order.

Question 4: Which of the following compounds has the functional group -OH?
(a) 1,2-Ethanediol
(b) 2-Butanone
(c) Nitrobenzene
(d) Ethanal
Show Answer & Explanation

Answer: (a) 1,2-Ethanediol

Explanation:
1. 1,2-Ethanediol is \( \ce{HOCH2CH2OH} \), an alcohol with two OH groups
2. 2-Butanone is a ketone, nitrobenzene a nitro compound and ethanal an aldehyde

Teacher's Note:
1. Eliminate options with an incorrect parent chain length first.
2. Then compare locants and alphabetical order among the remaining options.

Question 5: The IUPAC name of \( \ce{CH3-CH(OH)-CH2-CH(CH2CH3)-CH3} \) is
(a) 4-Ethyl-2-pentanol
(b) 4-Methyl-2-hexanol
(c) 2-Ethyl-4-pentanol
(d) 3-Methyl-2-hexanol
Show Answer & Explanation

Answer: (b) 4-Methyl-2-hexanol

Explanation:
1. The longest chain containing the OH carbon runs through the ethyl group and has six carbons (hexane)
2. Numbering from the OH end puts OH on C-2 and the methyl on C-4: 4-methylhexan-2-ol

Teacher's Note:
1. Draw the carbon skeleton out in full before naming; it prevents mistakes with branches.
2. Check that the principal group has the lowest possible locant.

Question 6: The IUPAC name of \( \ce{CH3-CH=C(CH3)-CH2-CH3} \) is
(a) 2-Ethyl-2-butene
(b) 3-Ethyl-2-butene
(c) 3-Methyl-3-pentene
(d) 3-Methyl-2-pentene
Show Answer & Explanation

Answer: (d) 3-Methyl-2-pentene

Explanation:
1. The longest chain containing the double bond has five carbons
2. Numbering from the \( \ce{=CH} \) end gives the double bond at C-2 and the methyl at C-3: 3-methylpent-2-ene

Teacher's Note:
1. Eliminate options with an incorrect parent chain length first.
2. Then compare locants and alphabetical order among the remaining options.

Question 7: Which compound is 2,2,3-trimethylhexane?
(a) \( \ce{CH3-C(CH3)2-CH(CH3)-CH2-CH3} \)
(b) \( \ce{CH3-C(CH3)2-CH2-CH(CH3)-CH3} \)
(c) \( \ce{CH3-C(CH3)2-CH(CH3)-CH2-CH2-CH3} \)
(d) \( \ce{CH3-CH(CH3)-CH2-CH2-C(CH3)2-CH3} \)
Show Answer & Explanation

Answer: (c) \( \ce{CH3-C(CH3)2-CH(CH3)-CH2-CH2-CH3} \)

Explanation:
1. The parent chain must have six carbons with two methyls on C-2 and one on C-3
2. Only (c) has this; (a) is 2,2,3-trimethylpentane, (b) is 2,2,4-trimethylpentane and (d) is 2,2,5-trimethylhexane

Teacher's Note:
1. Draw the carbon skeleton out in full before naming; it prevents mistakes with branches.
2. Check that the principal group has the lowest possible locant.

Question 8: The IUPAC name of \( \ce{CH3CH2COCH2CH3} \) is
(a) 3-Pentanone
(b) 2-Pentanone
(c) Diethyl ketone
(d) All the above
Show Answer & Explanation

Answer: (a) 3-Pentanone

Explanation:
1. The carbonyl carbon is the middle of a five-carbon chain
2. So the IUPAC name is pentan-3-one (diethyl ketone is the common name and 2-pentanone is a different compound)

Teacher's Note:
1. Eliminate options with an incorrect parent chain length first.
2. Then compare locants and alphabetical order among the remaining options.

Question 9: The IUPAC name of \( \ce{(CH3)2CH-CH=CH-CH3} \) is
(a) 2-Methyl-3-pentene
(b) 4-Methyl-2-pentene
(c) 1,2-Dimethyl-2-butene
(d) 3-Methyl-4-pentene
Show Answer & Explanation

Answer: (b) 4-Methyl-2-pentene

Explanation:
1. The five-carbon chain is numbered from the end nearer the double bond
2. The double bond is at C-2 and the methyl at C-4

Teacher's Note:
1. Draw the carbon skeleton out in full before naming; it prevents mistakes with branches.
2. Check that the principal group has the lowest possible locant.

Question 10: The IUPAC name of \( \ce{CH2=CH-CH(CH3)2} \) is
(a) 1,1-Dimethyl-2-propene
(b) 3-Methyl-1-butene
(c) 2-Vinylpropane
(d) 1-Isopropylethylene
Show Answer & Explanation

Answer: (b) 3-Methyl-1-butene

Explanation:
1. The longest chain containing C=C has four carbons, numbered from the double-bond end
2. The methyl group is on C-3: 3-methylbut-1-ene

Teacher's Note:
1. Eliminate options with an incorrect parent chain length first.
2. Then compare locants and alphabetical order among the remaining options.

Question 11: The IUPAC name of \( \ce{CH3CH2CH(CH3)CH2CH2CH3} \) is
(a) 4-Methylhexane
(b) 3-Methylhexane
(c) 2-Propylbutane
(d) 2-Ethylpentane
Show Answer & Explanation

Answer: (b) 3-Methylhexane

Explanation:
1. The longest chain has six carbons
2. Numbering from the end nearer the methyl gives locant 3, so 3-methylhexane

Teacher's Note:
1. Draw the carbon skeleton out in full before naming; it prevents mistakes with branches.
2. Check that the principal group has the lowest possible locant.

Question 12: The general formula of alkynes is
(a) \( \ce{CnH2n+2} \)
(b) \( \ce{CnH2n} \)
(c) \( \ce{CnH2n-2} \)
(d) \( \ce{CnHn} \)
Show Answer & Explanation

Answer: (c) \( \ce{CnH2n-2} \)

Explanation:
1. An alkyne has one triple bond, which removes four hydrogens from the alkane formula
2. So \( \ce{CnH2n+2} \) becomes \( \ce{CnH2n-2} \)

Teacher's Note:
1. Find the principal functional group first, then the longest chain containing it, then number for the lowest locants.
2. Write substituent prefixes in alphabetical order.

Question 13: The IUPAC name of the compound with structure \( \ce{CH3-CHCl2} \) (carbon 1 bearing two Cl atoms) is
(a) 1,2-Dichloroethane
(b) 2,2-Dichloroethane
(c) 1,1-Dichloroethane
(d) Dichloroethane
Show Answer & Explanation

Answer: (c) 1,1-Dichloroethane

Explanation:
1. Both chlorine atoms are on the same carbon, which is numbered 1
2. So the name is 1,1-dichloroethane

Teacher's Note:
1. Draw the carbon skeleton out in full before naming; it prevents mistakes with branches.
2. Check that the principal group has the lowest possible locant.

Question 14: The IUPAC name of \( \ce{CH3-CH(CH3)-CH2-CH=CH2} \) is
(a) 2-Methylpentene
(b) 4-Methylpent-1-ene
(c) 1-Hexene
(d) 2-Methylpent-1-ene
Show Answer & Explanation

Answer: (b) 4-Methylpent-1-ene

Explanation:
1. Number from the double-bond end: C=C at C-1
2. The methyl group is then on C-4

Teacher's Note:
1. Find the principal functional group first, then the longest chain containing it, then number for the lowest locants.
2. Write substituent prefixes in alphabetical order.

Question 15: In the structure \( \ce{CH3-C(CH3)2-CH2-CH3} \), numbered C-1 to C-4 along the main chain (C-1 = \( \ce{CH3} \), C-2 = the carbon bearing the two extra methyl groups), the quaternary carbon atom is
(a) C-1
(b) C-2
(c) C-3
(d) C-5
Show Answer & Explanation

Answer: (b) C-2

Explanation:
1. A quaternary carbon is bonded to four other carbon atoms
2. Only C-2 (bonded to C-1, C-3 and two methyl groups) fits

Teacher's Note:
1. Draw the carbon skeleton out in full before naming; it prevents mistakes with branches.
2. Check that the principal group has the lowest possible locant.

Question 16: The IUPAC name of \( \ce{CH3C#C-CH(CH3)2} \) is
(a) 4-Methyl-2-pentyne
(b) 4,4-Dimethyl-2-butyne
(c) Methyl isopropyl acetylene
(d) 2-Methyl-4-pentyne
Show Answer & Explanation

Answer: (a) 4-Methyl-2-pentyne

Explanation:
1. The triple bond is given the lowest locant, so numbering starts from the \( \ce{CH3-C#} \) end
2. C#C is at C-2 and the methyl is on C-4

Teacher's Note:
1. Find the principal functional group first, then the longest chain containing it, then number for the lowest locants.
2. Write substituent prefixes in alphabetical order.

Question 17: The IUPAC name of \( \ce{CH3-CH(CH3)-C(=CH2)-CH2CH3} \) is
(a) 3-Methyl-2-ethylbut-1-ene
(b) 2-Ethyl-3-methylbut-1-ene
(c) 3-Ethyl-2-methylbut-1-ene
(d) Ethylisopropylethene
Show Answer & Explanation

Answer: (b) 2-Ethyl-3-methylbut-1-ene

Explanation:
1. The chain \( \ce{CH2=C-CH-CH3} \) has four carbons with C=C at C-1
2. Ethyl is on C-2 and methyl on C-3, and prefixes are listed alphabetically: 2-ethyl-3-methylbut-1-ene

Teacher's Note:
1. Draw the carbon skeleton out in full before naming; it prevents mistakes with branches.
2. Check that the principal group has the lowest possible locant.

Question 18: The IUPAC name of \( \ce{CH3-CH(C6H5)-CH2-CH3} \) is
(a) 2-Cyclohexylbutane
(b) 2-Phenylbutane
(c) 3-Cyclohexylbutane
(d) 3-Phenylbutane
Show Answer & Explanation

Answer: (b) 2-Phenylbutane

Explanation:
1. The parent chain is butane and \( \ce{C6H5} \) is a phenyl group on C-2
2. Locants are kept lowest, so 2-phenylbutane

Teacher's Note:
1. Find the principal functional group first, then the longest chain containing it, then number for the lowest locants.
2. Write substituent prefixes in alphabetical order.

Question 19: The IUPAC name of \( \ce{CH3-CH(CH2CH3)-CHO} \) is
(a) Butan-2-aldehyde
(b) 2-Methylbutanal
(c) 3-Methylisobutyraldehyde
(d) 2-Ethylpropanal
Show Answer & Explanation

Answer: (b) 2-Methylbutanal

Explanation:
1. The longest chain with the CHO carbon has four carbons
2. A methyl group sits on C-2, giving 2-methylbutanal

Teacher's Note:
1. Eliminate options with an incorrect parent chain length first.
2. Then compare locants and alphabetical order among the remaining options.

Question 20: The IUPAC name of \( \ce{CH3-CH(CH3)-CH2-CH2-OH} \) is
(a) 1-Pentanol
(b) Pentanol
(c) 2-Methyl-4-butanol
(d) 3-Methyl-1-butanol
Show Answer & Explanation

Answer: (d) 3-Methyl-1-butanol

Explanation:
1. Number from the OH end so that OH is on C-1
2. The methyl group is on C-3

Teacher's Note:
1. Find the principal functional group first, then the longest chain containing it, then number for the lowest locants.
2. Write substituent prefixes in alphabetical order.

Question 21: The IUPAC name of tertiary butyl alcohol is
(a) Butan-1-ol
(b) Butan-2-ol
(c) 2-Methylpropan-1-ol
(d) 2-Methylpropan-2-ol
Show Answer & Explanation

Answer: (d) 2-Methylpropan-2-ol

Explanation:
1. Tertiary butyl alcohol is \( \ce{(CH3)3C-OH} \)
2. The OH and one methyl are on C-2 of propane: 2-methylpropan-2-ol

Teacher's Note:
1. Eliminate options with an incorrect parent chain length first.
2. Then compare locants and alphabetical order among the remaining options.

Question 22: The IUPAC name of \( \ce{CH3-CH(CH3)-CH=CH-CH2-COOH} \) is
(a) 5-Methyl-3-hexenoic acid
(b) 5-Methyl-2-pentene-1-carboxylic acid
(c) 4-Isopropyl-3-butenoic acid
(d) None of the above
Show Answer & Explanation

Answer: (a) 5-Methyl-3-hexenoic acid

Explanation:
1. C-1 is the COOH carbon and the chain has six carbons
2. The double bond is at C-3 and the methyl at C-5: 5-methylhex-3-enoic acid

Teacher's Note:
1. Find the principal functional group first, then the longest chain containing it, then number for the lowest locants.
2. Write substituent prefixes in alphabetical order.

Question 23: The structure of 4-methylpent-2-ene is
(a) \( \ce{(CH3)2CH-CH2-CH=CH2} \)
(b) \( \ce{(CH3)2CH-CH=CH-CH3} \)
(c) \( \ce{(CH3)2CH-CH2CH=CH-CH3} \)
(d) \( \ce{(CH3)2C=CH-CH2CH3} \)
Show Answer & Explanation

Answer: (b) \( \ce{(CH3)2CH-CH=CH-CH3} \)

Explanation:
1. Pent-2-ene is \( \ce{CH3-CH=CH-CH2-CH3} \) (five carbons, double bond after C-2) numbered from the other end as \( \ce{CH3-CH=CH-CH(CH3)-CH3} \)
2. A methyl on C-4 gives \( \ce{(CH3)2CH-CH=CH-CH3} \)

Teacher's Note:
1. Eliminate options with an incorrect parent chain length first.
2. Then compare locants and alphabetical order among the remaining options.

Practice MCQs for JEE Chemistry Organic Chemistry Some Basic Principles and Techniques

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