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Organic Chemistry – Some Basic Principles and Techniques · Question 5

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1

The most stable carbocation among the following is :

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

Answer

(4) [figure]

Solution

Stability of carbocations: 3 > 2 > 1 (more alkyl groups → more +I effect and hyperconjugation).

(1) 2 carbocation

(2) 2 carbocation

(3) 1 carbocation

(4) 1-Methylcyclohexyl cation: 3 carbocation with the most α-hydrogens for hyperconjugation → most stable.

Answer: (4)

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2

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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3

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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4

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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5

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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6

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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7

Which compound amongst the following is not an aromatic compound?

  1. [figure]
  2. [figure]
  3. [figure]
  4. [figure]
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8

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

  1. 1-bromo-5-chloro-4-methylhexan-3-ol
  2. 6-bromo-2-chloro-4-methylhexan-4-ol
  3. 1-bromo-4-methyl-5-chlorohexan-3-ol
  4. 6-bromo-4-methyl-2-chlorohexan-4-ol
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9

What is the hybridization shown by C1 and C2 carbons, respectively in the given compound? OHC- 1CH=CH- 2CH2COOCH3

  1. sp3 and sp3
  2. sp2 and sp3
  3. sp2 and sp2
  4. sp3 and sp2
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10

Which of the following is the most stable carbocation?

  1. [figure]
  2. [figure]
  3. [figure]
  4. [figure]
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11

The correct structure of 2, 6-dimethyl-dec-4-ene is

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