Alkyl Halides

10.
E: Organohalides (Exercises)
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o 9.E: Alkynes: An Introduction to Organic Synthesis (Exercises)

o 11.E: Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations
(Exercises)
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These are the homework exercises to accompany the Textmap for McMurry's Organic Chemistry
textbook.
10.0 Introduction
10.1 Names and Properties of Alkyl Halides
10.1 Exercises
Questions
Q10.1.1
Give the names of the following organohalides:

Q10.1.2
Draw the structures of the following compounds:
A – 2-Chloro-3,3-dimethylpentane
B – 1,1-Dichloro-4-isopropylcyclohexane
C – 3-bromo-3-ethylhexane
Solutions
S10.1.1
A – 5-ethyl-4-iodo-3methyl-octane
B – 1-bromo-2,3,4-trimethyl-pentane
C – 4-bromo-5-chloro-2-methyl-heptane
S10.1.2
10.2 Preparing Alkyl Halides from Alkanes: Radical
Halogenation
10.2 Exercises
Questions
Q10.2.1
Predict the mono-substituted halogenated product(s) of chlorine gas reacting with 2-

methylbutane.
Q10.2.2
Predict the relative amount of each mono-brominated product when 3-methylpentane is reacted
with Br2. Consider 1°, 2°, 3° hydrogen.
Solutions
S10.2.1
S10.2.2
10.3 Preparing Alkyl Halides from Alkenes: Allylic

Bromination
10.4 Stability of the Allyl Radical: Resonance
Revisited
10.4 Exercises
Questions
Q10.4.1
The following reaction shows the major product. Explain why this would be the final product
and why the 2° bromo product is not the major product.
Q10.4.2
Predict the products of the following reactions:
Solutions
S10.4.1
The product (A) is a 1° halogen which is more predominant product even though the (B) had a
better transition state with a 2° radical. The 1° radical intermediate is not as sterically hindered.
S10.4.2
10.5 Preparing Alkyl Halides from Alcohols
10.5 Exercises
Questions
Q10.5.1
Predict the alcohol required for the synthesis of the following halides:
Solutions
S10.5.1
10.6 Reactions of Alkyl Halides: Grignard Reagents
10.6 Exercises
Questions
Q10.6.1
How strong of a base would you expect ethyl Grignard to be? Would the following reactions be
able to take place?
Q10.6.2
How would you make a deuterated compound from an alkyl halide?
Solutions
S10.6.1
Because hydrocarbons like ethane are very weak acids (pKa = 50), then the corresponding
carbanion (CH3CH2-) is expected to be a strong base. Both reactions will occur.
S10.6.2
By first making a Grignard and then exposing it to heavy water.

10.7 Organometallic Coupling Reactions
10.8 Oxidation and Reduction in Organic Chemistry
10.8 Exercises
Questions
Q10.8.1
In each case state whether the reaction is an oxidation or reduction of the organic compound.
Solutions
S10.8.1
A – Reduction
B – Oxidation
11.E: Reactions of Alkyl Halides:

Nucleophilic Substitutions and Eliminations
(Exercises)
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2. Last updated
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o 10.E: Organohalides (Exercises)

o 12.E: Structure Determination: Mass Spectrometry and Infrared Spectroscopy
(Exercises)
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These are the homework exercises to accompany the Textmap for McMurry's Organic Chemistry
textbook.
11.1 The Discovery of Nucleophilic Substitution

Reactions
11.1 Exercises
Questions
Q11.1.1
Predict the product of a nucleophilic substitution of (S)-2-bromopentane reacting with CH3CO2-,

Show stereochemistry.
Solutions
S11.1.1
11.2 The SN2SN2 Reaction

11.3 Characteristics of the SN2SN2 Reaction
11.3 Exercises
Questions
Q11.3.1
What product(s) do you expect from the reaction of 1-bromopentane with each of the following
reagents in an SN2 reaction?
A – KI
B – NaOH
C - CH3C≡C-Li
D – NH3
Q11.3.2
Which in the following pairs is a better nuceophile?
A - (CH3CH2)2N- or (CH3CH2)2NH
B - (CH3CH2)3N or (CH3CH2)3B
C – H2O or H2S
Q11.3.3
Order the following in increasing reactivity for an SN2 reaction.
CH3CH2Br CH3CH2OTos (CH3CH2)3CCl (CH3CH2)2CHCl
Q11.3.4
Solvents benzene, ether, chloroform are non-polar and not strongly polar solvents. What effects
do these solvents have on an SN2 reaction?
Solutions
S11.3.1
S11.3.2
A - (CH3CH2)2N- as there is a charge present on the nitrogen.
B - (CH3CH2)3N because a lone pair of electrons is present.
C - H2O as oxygen is more electronegative.
S11.3.3
S11.3.4
They will decrease the reactivity of the reaction.
11.4 The SN1SN1 Reaction

11.4 Exercises
Questions
Q11.4.1
Give the products of the following SN1 reaction. Show stereochemistry.

Solutions
S11.4.1
11.5 Characteristics of the SN1SN1 Reaction

11.5 Exercises
Questions
Q11.5.1
Rank the following by increasing reactivity in an SN1 reaction.

Q11.5.2
3-bromo-1-pentene and 1-bromo-2-pentene undergo SN1 reaction at almost the same rate, but one
is a secondary halide while the other is a primary halide. Explain why this is.
Q11.5.3
Label the following reactions as most likely occuring by an SN1 or SN2 mechanism. Suggest why.
Solutions
S11.5.1
Consider the stability of the intermediate, the carbocation.
A < D < B < C (most reactive)
S11.5.2
They have the same intermediates when you look at the resonance forms.
S11.5.3
A – SN1 *poor leaving group, protic solvent, secondary cation intermediate
B – SN2 *good leaving group, polar solvent, primary position.
11.6 Biological Substitution Reactions

11.7 Elimination Reactions: Zaitsev's Rule
11.7 Exercises
Questions
Q11.7.1
Ignoring the alkene stereochemistry show the elimination product(s) of the following
compounds:
Solutions
S11.7.1
11.8 The E2E2 Reaction and the Deuterium Isotope
Effect
11.8 Exercises
Questions
Q11.8.1
What is the product of the following molecule in an E2 reaction? What is the stereochemistry?
Solutions
S11.8.1
The stereochemistry is (Z) for the reaction.
11.9 The E2E2 Reaction and Cyclohexane

Conformation
11.9 Exercises
Questions
Q11.9.1
Which of the following compounds will react faster in an E2 reaction; trans-1-bromo-2-

isopropylcyclohexane or cis-1-bromo-2-isopropylcyclohexane?
Solutions
S11.9.1
The cis isomer will react faster than the trans. The cis isomer has two possible perpendicular
hydrogen in which it can eliminate from.
11.0 Introduction
11.10 The E1E1 and E1E1 cB Reactions
11.11 Biological Elimination Reactions
11.12 A Summary of Reactivity: SN1SN1, SN2SN2,
E1E1, E1E1cB, and E2E2
11.12 Exercises
Questions
Q11.12.1
Label the following reactions as SN1, SN2, E1, or E2.

Solutions
S11.12.1
A – S N2
B – E1
C – S N1
D – E2

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10.

Give the names of the following organohalides:

Draw the structures of the following compounds:

Predict the mono-substituted halogenated product(s) of chlorine gas reacting with 2-

10.3 Preparing Alkyl Halides from Alkenes: Allylic

Predict the products of the following reactions:

How would you make a deuterated compound from an alkyl halide?

By first making a Grignard and then exposing it to heavy water.

11.E: Reactions of Alkyl Halides:

11.1 The Discovery of Nucleophilic Substitution

Predict the product of a nucleophilic substitution of (S)-2-bromopentane reacting with CH3CO2-,

11.2 The SN2SN2 Reaction

Which in the following pairs is a better nuceophile?

Order the following in increasing reactivity for an SN2 reaction.

CH3CH2Br CH3CH2OTos (CH3CH2)3CCl (CH3CH2)2CHCl

A - (CH3CH2)2N- as there is a charge present on the nitrogen.

B - (CH3CH2)3N because a lone pair of electrons is present.

C - H2O as oxygen is more electronegative.

They will decrease the reactivity of the reaction.

11.4 The SN1SN1 Reaction

Give the products of the following SN1 reaction. Show stereochemistry.

11.5 Characteristics of the SN1SN1 Reaction

Rank the following by increasing reactivity in an SN1 reaction.

Consider the stability of the intermediate, the carbocation.

A < D < B < C (most reactive)

A – SN1 *poor leaving group, protic solvent, secondary cation intermediate

B – SN2 *good leaving group, polar solvent, primary position.

11.6 Biological Substitution Reactions

The stereochemistry is (Z) for the reaction.

11.9 The E2E2 Reaction and Cyclohexane

Which of the following compounds will react faster in an E2 reaction; trans-1-bromo-2-

Label the following reactions as SN1, SN2, E1, or E2.

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