JEE Chemistry Organic Chemistry Some Basic Principles and Techniques MCQs Set 37

Chemistry Objective Questions and Answers: Organic Chemistry Some Basic Principles and Techniques

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Multiple Choice Questions

Question 1: The general formula of alkanes is
(a) \( \ce{CnH2n+1} \)
(b) \( \ce{CnH2n+2} \)
(c) \( \ce{CnH2n-1} \)
(d) \( \ce{CnH2n} \)
Show Answer & Explanation

Answer: (b) \( \ce{CnH2n+2} \)

Explanation:
1. Alkanes are saturated, with every carbon singly bonded
2. The formula is \( \ce{CnH2n+2} \)

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 2: The general formulae of alkene and alkane are respectively
(a) \( \ce{CnH2n} \) and \( \ce{CnH2n+1} \)
(b) \( \ce{CnH2n} \) and \( \ce{CnH2n+2} \)
(c) \( \ce{CnH2n-1} \) and \( \ce{CnH2n} \)
(d) \( \ce{CnH2n-1} \) and \( \ce{CnH2n+2} \)
Show Answer & Explanation

Answer: (b) \( \ce{CnH2n} \) and \( \ce{CnH2n+2} \)

Explanation:
1. An alkene has one C=C and so two fewer hydrogens than the alkane
2. Alkene \( \ce{CnH2n} \), alkane \( \ce{CnH2n+2} \)

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 3: The general formula of paraffins is
(a) \( \ce{CnH2n} \)
(b) \( \ce{CnH2n-2} \)
(c) \( \ce{CnH2n+2} \)
(d) \( \ce{C2nH2n} \)
Show Answer & Explanation

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

Explanation:
1. Paraffins are the alkanes
2. Their formula is \( \ce{CnH2n+2} \)

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 4: The IUPAC name of \( \ce{CH3CH2-CH(CH3)-CH2-COCl} \) is
(a) 3-Methylpentanoyl chloride
(b) 3-Methylbutanoyl chloride
(c) 1-Chloro-3-methylpentanol
(d) None of these
Show Answer & Explanation

Answer: (a) 3-Methylpentanoyl chloride

Explanation:
1. The COCl carbon is C-1 of a five-carbon chain
2. A methyl is on C-3

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 5: The IUPAC name of \( \ce{ClH2C-C(Br)=C(Br)-CH2Cl} \) is
(a) 2,3-Dibromo-1,4-dichlorobut-2-ene
(b) 1,4-Dichloro-2,3-dibromobut-2-ene
(c) Dichlorodibromobutene
(d) Dichlorodibromobutane
Show Answer & Explanation

Answer: (a) 2,3-Dibromo-1,4-dichlorobut-2-ene

Explanation:
1. The four-carbon chain has the double bond at C-2
2. Substituents are Br on C-2 and C-3, Cl on C-1 and C-4, listed alphabetically (bromo before chloro)

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 6: The IUPAC name of acraldehyde is
(a) Prop-2-en-1-al
(b) Propenal aldehyde
(c) But-2-en-1-al
(d) Propenal acid
Show Answer & Explanation

Answer: (a) Prop-2-en-1-al

Explanation:
1. Acraldehyde is \( \ce{CH2=CH-CHO} \)
2. Its IUPAC name is prop-2-en-1-al (propenal)

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 7: Cycloalkanes have the general formula
(a) \( \ce{CnH2n+2} \)
(b) \( \ce{CnH2n-2} \)
(c) \( \ce{CnH2n} \)
(d) \( \ce{C2nH2} \)
Show Answer & Explanation

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

Explanation:
1. Ring closure removes two hydrogens from the alkane formula
2. So cycloalkanes are \( \ce{CnH2n} \)

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 8: The IUPAC name of \( \ce{CH3-CH(C2H5)-CH=CH-CH3} \) is
(a) 4-Ethyl-2-pentene
(b) 4-Methylhex-2-ene
(c) 3-Ethyl-2-pentene
(d) 2-Ethyl-3-pentene
Show Answer & Explanation

Answer: (b) 4-Methylhex-2-ene

Explanation:
1. The longest chain including C=C has six carbons, numbered from the double-bond end
2. The double bond is at C-2 and the methyl at 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 9: The IUPAC name of \( \ce{CH3-CH(CH3)-CH2-CH(CN)-CH3} \) is
(a) 2-Cyano-3-methylhexane
(b) 3-Methyl-5-cyanohexane
(c) 2,4-Dimethylpentanenitrile
(d) 2-Cyano-3-methylhexane nitrile
Show Answer & Explanation

Answer: (c) 2,4-Dimethylpentanenitrile

Explanation:
1. The CN carbon is C-1, so the chain is a five-carbon nitrile
2. Methyl groups on C-2 and C-4 give 2,4-dimethylpentanenitrile

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 \( \ce{CH3CH2-CH(OCH3)-CH2OH} \) is
(a) 2-Methoxybutan-1-ol
(b) 3-Methoxybutan-1-ol
(c) 3-Methoxybutan-2-ol
(d) 1,2-Methoxybutanol
Show Answer & Explanation

Answer: (a) 2-Methoxybutan-1-ol

Explanation:
1. OH is the principal group and takes C-1 of the four-carbon chain
2. OCH3 is a methoxy substituent on C-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 11: The IUPAC name of \( \ce{CH3-CH(NH2)-CH3} \) is
(a) Dimethylamine
(b) Propan-2-amine
(c) Isopropylamine
(d) 2-Propanamine acid
Show Answer & Explanation

Answer: (b) Propan-2-amine

Explanation:
1. The amine group is on C-2 of propane
2. The systematic name is propan-2-amine (isopropylamine is a common name)

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 IUPAC name of \( \ce{CH3-CHCl-CH3} \) is
(a) 2-Chloropropane
(b) Chloropropane
(c) 1-Chloropropane
(d) 2-Chlorobutane
Show Answer & Explanation

Answer: (a) 2-Chloropropane

Explanation:
1. Cl is on the middle carbon of propane
2. The name is 2-chloropropane

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 names of \( \ce{CH3-C(CH3)(OH)-CH2-CH(OH)-CH3} \) and \( \ce{NC-CH2-CH(CN)-CH2-CN} \) are respectively
(a) 1,1-Dimethyl-1,3-butanediol and propanetricarbylamine
(b) 4-Methyl-2,4-pentanediol and 1,2,3-propanetrinitrile
(c) 2-Methyl-2,4-pentanediol and 3-cyano-1,5-pentanedinitrile
(d) 1,3,3-Trimethyl-1,3-propanediol and 1,2,3-tricyanopropane
Show Answer & Explanation

Answer: (c) 2-Methyl-2,4-pentanediol and 3-cyano-1,5-pentanedinitrile

Explanation:
1. The diol is numbered to give OH the locants 2 and 4, with a methyl on C-2
2. The trinitrile is a five-carbon dinitrile chain with a cyano substituent on C-3

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 the compound is
(a) alpha-Methylcyclohexanone
(b) 2-Methylcyclohexanone
(c) Heptanone-2
(d) Methylcyclohexanone-1
Show Answer & Explanation

Answer: (b) 2-Methylcyclohexanone

Explanation:
1. The carbonyl carbon is C-1 of the ring
2. A methyl on the adjacent carbon gives 2-methylcyclohexanone

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: The IUPAC name of \( \ce{CH2=CH-CH(C2H5)-C(Br)=CH2} \) is
(a) 4-Bromo-3-ethylpenta-1,4-diene
(b) 2-Bromo-3-ethylpenta-1,4-diene
(c) 2-Bromo-3-ethylpenta-1,5-diene
(d) None of these
Show Answer & Explanation

Answer: (b) 2-Bromo-3-ethylpenta-1,4-diene

Explanation:
1. The five-carbon chain has C=C at C-1 and C-4 (locants 1,4 are lower than 1,5)
2. Br is on C-2 and ethyl on C-3

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 16: The IUPAC name of \( \ce{CH3CH2COOH} \) is
(a) Ethyl formic acid
(b) Ethylcarboxylic acid
(c) Ethanemethanoic acid
(d) Propanoic acid
Show Answer & Explanation

Answer: (d) Propanoic acid

Explanation:
1. The three-carbon acid (including the carboxyl carbon) is propanoic acid
2. The other names are not IUPAC

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 \( \ce{(CH3)3C-CH=CH2} \) is
(a) 3,3,3-Trimethylprop-1-ene
(b) 1,1,1-Trimethylprop-2-ene
(c) 3,3-Dimethylbut-1-ene
(d) 2,2-Dimethylbut-3-ene
Show Answer & Explanation

Answer: (c) 3,3-Dimethylbut-1-ene

Explanation:
1. The longest chain containing C=C has four carbons
2. Numbering from the double bond gives two methyls on C-3

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 18: The IUPAC name of \( \ce{CH3COCH(CH3)2} \) is
(a) Isopropyl methyl ketone
(b) 2-Methyl-3-butanone
(c) 4-Methylisopropyl ketone
(d) 3-Methyl-2-butanone
Show Answer & Explanation

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

Explanation:
1. The carbonyl carbon must get the lowest locant (2)
2. The methyl branch is then 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 19: The IUPAC name of \( \ce{CH3COCH3} \) is
(a) Dimethyl ketone
(b) Acetone
(c) Propanal
(d) Propanone
Show Answer & Explanation

Answer: (d) Propanone

Explanation:
1. Ketones take the suffix -one
2. Three carbons give propanone (acetone and dimethyl ketone are common names)

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 the compound is
(a) 3-Methylcyclohexene
(b) 1-Methylcyclohex-2-ene
(c) 6-Methylcyclohexene
(d) 1-Methylcyclohex-5-ene
Show Answer & Explanation

Answer: (a) 3-Methylcyclohexene

Explanation:
1. The double bond carbons are C-1 and C-2 in a ring
2. The methyl is on the carbon next to the double bond, numbered 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: What is the correct IUPAC name of the compound ?
(a) 4-Methoxy-2-nitrobenzaldehyde
(b) 4-Formyl-3-nitroanisole
(c) 4-Methoxy-6-nitrobenzaldehyde
(d) 2-Formyl-5-methoxynitrobenzene
Show Answer & Explanation

Answer: (a) 4-Methoxy-2-nitrobenzaldehyde

Explanation:
1. The aldehyde group is principal, so its ring carbon is C-1
2. NO2 is on C-2 and OCH3 on C-4

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 \( \ce{CH3-CO-CH2-COOH} \) is
(a) 3-Oxobutanoic acid
(b) 2-Oxobutanoic acid
(c) 4-Oxobutanoic acid
(d) 3-Oxopropanoic acid
Show Answer & Explanation

Answer: (a) 3-Oxobutanoic acid

Explanation:
1. The COOH carbon is C-1 and the chain has four carbons
2. The C=O group is on C-3 and is named as an oxo prefix

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 23: The IUPAC name of the compound is
(a) 1,2-Epoxybutane
(b) Ethyl methyl ether
(c) Keto pentanone
(d) None of these
Show Answer & Explanation

Answer: (a) 1,2-Epoxybutane

Explanation:
1. The ring contains one oxygen and the carbon chain has four carbons
2. The epoxide bridges C-1 and C-2 of butane: 1,2-epoxybutane (2-ethyloxirane)

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 24: The IUPAC name of \( \ce{CH3-CH(CH3)-CH(CH3)-C#C-CH3} \) is
(a) 2,3-Dimethyl-4-hexyne
(b) 4,5-Dimethyl-2-hexyne
(c) 5-Propyl-2-pentyne
(d) 2-Propyl-3-pentyne
Show Answer & Explanation

Answer: (b) 4,5-Dimethyl-2-hexyne

Explanation:
1. The triple bond gets the lowest locant, so numbering starts from the \( \ce{CH3-C#} \) end
2. Triple bond at C-2, methyls on C-4 and C-5

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.

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