Organic Chemistry, 9e,

Global Edition
by L. G. Wade, Jr.

Clicker Questions

Chapter 6
Alkyl Halides:
Nucleophilic
Substitution

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 6.1 Give the IUPAC name for (CH3)2CBrCH2CH(CH3)2.

a) 2-Bromo-2,4-dimethylpentane
b) 4-Bromo-2,4-dimethylpentane
c) 2-Bromopentane
d) 2-Bromoheptane
e) Isobutyl isopentyl bromide

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 6.1 Give the IUPAC name for (CH3)2CBrCH2CH(CH3)2.

a) 2-Bromo-2,4-dimethylpentane
b) 4-Bromo-2,4-dimethylpentane
c) 2-Bromopentane
d) 2-Bromoheptane
e) Isobutyl isopentyl bromide

Explanation:
Pentane is the longest continuous chain.

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 6.2 Give the IUPAC name for CH3CH(Cl)C(Br)2CH3.

a) 2-Chloro-3-bromobutane
b) 2,2-Dibromopentane
c) 3-Chloro-2-bromobutane
d) 2,2-Dibromo-3-chlorobutane
e) 2-Chloro-3,3-dibromobutane

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 6.2 Give the IUPAC name for CH3CH(Cl)C(Br)2CH3.

a) 2-Chloro-3-bromobutane
b) 2,2-Dibromopentane
c) 3-Chloro-2-bromobutane
d) 2,2-Dibromo-3-chlorobutane
e) 2-Chloro-3,3-dibromobutane

Explanation:
Butane is the longest chain.

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 6.3 Name .

a) Isobutyl bromide
b) Neopentyl bromide
c) tert-Butyl bromide
d) tert-Pentyl bromide

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 6.3 Name .

a) Isobutyl bromide
b) Neopentyl bromide
c) tert-Butyl bromide
d) tert-Pentyl bromide

Explanation:
Five carbons are present in the structure and are used in the
common name.
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 6.4 Identify the vinyl chloride.

a) ClCH2CH=CH2
b) ClCH=CH2
c) C6H5Cl
d) CH3CH2Cl
e) CH3CH(Cl)CH3

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 6.4 Identify the vinyl chloride.

a) ClCH2CH=CH2
b) ClCH=CH2
c) C6H5Cl
d) CH3CH2Cl
e) CH3CH(Cl)CH3

Explanation:
A vinyl halide has a Cl attached to the double-bonded carbon.
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 6.5 Identify the secondary alkyl halide.

a) CH3Br
b) CH3CH2Br
c) CH3CH(Br)CH3
d) (CH3)3CBr

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 6.5 Identify the secondary alkyl halide.

a) CH3Br
b) CH3CH2Br
c) CH3CH(Br)CH3
d) (CH3)3CBr

Explanation:
In a secondary alkyl halide, the halogen is attached to a
carbon, which is attached to two other carbons.
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 6.6 Identify the type of intermolecular attraction
between alkyl halides.

a) Hydrogen bonding
b) London forces
c) Dipole–dipole
d) None

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 6.6 Identify the type of intermolecular attraction
between alkyl halides.

a) Hydrogen bonding
b) London forces
c) Dipole–dipole
d) None

Explanation:
London forces are the strongest intermolecular attractions in
alkyl halides.
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 6.7

a) CH2BrCH2CH=CH2
b) CH3CH(Br)CH=CH2
c) CH3CH2CBr=CH2
d) CH3CH2CH=CHBr

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 6.7

a) CH2BrCH2CH=CH2
b) CH3CH(Br)CH=CH2
c) CH3CH2CBr=CH2
d) CH3CH2CH=CHBr

Explanation:
Br substitutes for H on the allylic carbon.

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 6.8

a) CH3CH2CHCl2
b) CH3CH(Cl)CHCl
c) CH3C(Cl)2CH3
d) CH3C(Cl)=CH2
e) CH3CH=CHCl

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 6.8

a) CH3CH2CHCl2
b) CH3CH(Cl)CHCl
c) CH3C(Cl)2CH3
d) CH3C(Cl)=CH2
e) CH3CH=CHCl

Explanation:
The HCl adds via Markovnikov orientation.
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 6.9 Identify the strongest nucleophile.

a) CH3OH
b) (CH3)3COH
c) CH3O–
d) (CH3)3CO–

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 6.9 Identify the strongest nucleophile.

a) CH3OH
b) (CH3)3COH
c) CH3O–
d) (CH3)3CO–

Explanation:
Negative nucleophiles are stronger than neutral nucleophiles.
Bulky nucleophiles are weaker.
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 6.10 Where does the nucleophile attack in an SN2
mechanism?

a) Back side
b) Front side
c) Both sides
d) Sideways

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 6.10 Where does the nucleophile attack in an SN2
mechanism?

a) Back side
b) Front side
c) Both sides
d) Sideways

Explanation:
The nucleophile attacks on the side opposite of the
leaving group.
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 6.11 Give the rate equation for an SN2 mechanism.

a) k[RX][RX]
b) k[RX][Nu]
c) k[Nu][Nu]
d) k[RX][B]

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 6.11 Give the rate equation for an SN2 mechanism.

a) k[RX][RX]
b) k[RX][Nu]
c) k[Nu][Nu]
d) k[RX][B]

Explanation:
The rate equation Ltdludes both the alkyl halide and
the nucleophile.
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 6.12 Identify the alkyl halide that reacts the fastest
in an SN1 mechanism.

a) CH3Cl
b) CH3CH2Cl
c) (CH3)2CHCl
d) (CH3)3CCl

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 6.12 Identify the alkyl halide that reacts the fastest
in an SN1 mechanism.

a) CH3Cl
b) CH3CH2Cl
c) (CH3)2CHCl
d) (CH3)3CCl

Explanation:
Tertiary alkyl halides react the fastest.

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 6.13 Identify the best solvent for an SN1 reaction.

a) CH3OCH3
b) (CH3)3N
c) CH3CH2OH
d) CCl4

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 6.13 Identify the best solvent for an SN1 reaction.

a) CH3OCH3
b) (CH3)3N
c) CH3CH2OH
d) CCl4

Explanation:
A protic solvent is the best solvent for an SN1 reaction. A
protic solvent has hydrogen bonding.
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 6.14 In an SN1 reaction, a 2° carbocation is formed.
What happens next?

a) Rearrangement may occur to form a 1° carbocation.

b) Rearrangement may occur to form a 3° carbocation.
c) The nucleophile attacks.
d) The leaving group departs.

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 6.14 In an SN1 reaction, a 2° carbocation is formed.
What happens next?

a) Rearrangement may occur to form a 1° carbocation.

b) Rearrangement may occur to form a 3° carbocation.
c) The nucleophile attacks.
d) The leaving group departs.

Explanation:
A more stable carbocation will be formed.

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 6.15 Give the IUPAC name for (CH3)2CHCH2Cl.

a) 1-Chloro-2-methylpropane
b) 1-Chloropropane
c) 1-Chlorobutane
d) 1-Chloro-3-methylpropane
e) 2-Chlorobutane

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 6.15 Give the IUPAC name for (CH3)2CHCH2Cl.

a) 1-Chloro-2-methylpropane
b) 1-Chloropropane
c) 1-Chlorobutane
d) 1-Chloro-3-methylpropane
e) 2-Chlorobutane

Explanation:
Propane is the longest continuous chain. Numbering is from
right to left.
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