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Organic Chemistry – Some Basic Principles and Techniques · Question 1

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1

The correct IUPAC name of the following compound is : [figure]

  1. 3-ethyl-5-methylheptane
  2. 3-methyl-5-ethylheptane
  3. 2,4-diethylhexane
  4. 3,5-diethylhexane

Answer

(1) 3-ethyl-5-methylheptane

Solution

Longest carbon chain = 7 C atoms (the horizontal chain) ⇒ parent: heptane

(A chain through the ethyl group also has only 7 C, so 2,4-diethylhexane / 3,5-diethylhexane are not the longest chain.)

Numbering from either end gives substituent locants 3 and 5 ⇒ the lower number goes to the group cited first in alphabetical order.

Ethyl before methyl ⇒ ethyl at C-3, methyl at C-5

∴ 3-ethyl-5-methylheptane

Answer: (1)

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2

The following carbocation is stabilized by the interaction of the empty p orbital with [figure]

  1. empty * and empty * orbitals
  2. filled and filled orbitals
  3. empty and empty * orbitals
  4. empty * and filled orbitals
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3

Arrange the following compounds in the increasing order of polarity A. CH3CH2OCH2CH3 B. CH3CH2OH C. CH3COCH3 D. CH3COOH Choose the correct answer from the options given below.

  1. A < C < B < D
  2. A < B < C < D
  3. C < A < D < B
  4. C < A < B < D
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4

Among the given compounds I-III, the correct order of bond dissociation energy of C-H bond marked with * is : [figure]

  1. III > II > I
  2. II > III > I
  3. II > I > III
  4. I > II > III
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5

The most stable carbocation among the following is :

  1. [figure]
  2. [figure]
  3. [figure]
  4. [figure]
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6

A compound with a molecular formula of C6H14 has two tertiary carbons. Its IUPAC name is :

  1. n-hexane
  2. 2-methylpentane
  3. 2,3-dimethylbutane
  4. 2,2-dimethylbutane
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7

The correct IUPAC name of the compound [figure] is :

  1. 4-ethyl-1-fluoro-2-nitrobenzene
  2. 4-ethyl-1-fluoro-6-nitrobenzene
  3. 3-ethyl-6-fluoro-1-nitrobenzene
  4. 1-ethyl-4-fluoro-3-nitrobenzene
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8

Methyl group attached to a positively charged carbon atom stabilizes the carbocation due to

  1. -I inductive effect
  2. electromeric effect
  3. hyperconjugation
  4. mesomeric effect
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9

The number of bonds, bonds and lone pair of electrons in pyridine, respectively are:

  1. 12, 3, 0
  2. 11, 3, 1
  3. 12, 2, 1
  4. 11, 2, 0
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10

Consider the following compounds/species: [figure] The number of compounds/species which obey Hückel's rule is .

  1. 6
  2. 2
  3. 5
  4. 4
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11

Which compound amongst the following is not an aromatic compound?

  1. [figure]
  2. [figure]
  3. [figure]
  4. [figure]
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