Essential Organic Chemistry

Paula Yurkanis Bruice

Chapter 8

Substitution and Elimination Reactions of Alkyl Halides - all with Video Answers

Educators

Chapter Questions

Problem 1

Methoxychlor is an insecticide that was intended to take DDT's place because it is not as soluble in fatty tissues and is more readily biodegradable. It, too, can accumulate in the environment, however, so its use was also banned-in 2002 in the European Union and in 2003 in the United States. Why is methoxychlor less soluble in fatty tissues than DDT?

Madeline Currie

Madeline Currie

Numerade Educator

Problem 2

How would the rate of the reaction between bromomethane and hydroxide ion be affected if the following changes in concentration are made?
a. The concentration of the alkyl halide is not changed and the concentration of the nucleophile is tripled.
b. The concentration of the alkyl halide is cut in half and the concentration of the nucleophile is not changed.

Anupa Sharad Medhekar

Anupa Sharad Medhekar

Numerade Educator

Problem 3

Does increasing the energy barrier for an $\mathrm{S}_{\mathrm{N}} 2$ reaction increase or decrease the magnitude of the rate constant for the reaction?

Madeline Currie

Madeline Currie

Numerade Educator

Problem 4

Arrange the following alkyl bromides in order from most reactive to least reactive in an $\mathrm{S}_{\mathrm{N}} 2$ reaction: 1-bromo-2-methylbutane, 1-bromo-3-methylbutane, 2-bromo-2-methylbutane, and 1-bromopentane.

Anupa Sharad Medhekar

Anupa Sharad Medhekar

Numerade Educator

Problem 5

Draw the products obtained from the $S_{N} 2$ reaction of
a. 2-bromobutane and methoxide ion.
c. $(S)-3$-chlorohexane and hydroxide ion.
b. $(R)-2$-bromobutane and methoxide ion.
d. 3-iodopentane and hydroxide ion.

Madeline Currie

Madeline Currie

Numerade Educator

Problem 6

Draw the substitution products that will be formed from the following $\mathrm{S}_{\mathrm{N}} 2$ reactions:
a. cis-1-bromo-4-methylcyclohexane and hydroxide ion
b. trans-1-iodo-4-ethylcyclohexane and methoxide ion
c. cis-1-chloro-3-methylcyclobutane and ethoxide ion

Madeline Currie

Madeline Currie

Numerade Educator

Problem 7

Which alkyl halide would you expect to be more reactive in an $\mathrm{S}_{\mathrm{N}} 2$ reaction with a given nucleophile? In each case, you can assume that both alkyl halides have the same stability.

Allison Krajewski

Allison Krajewski

Numerade Educator

Problem 8

Which reaction in each of the following pairs occurs faster?
a. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Br}+\mathrm{H}_{2} \mathrm{O}$ or $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Br}+\mathrm{HO}^{-}$
b. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Cl}+\mathrm{CH}_{3} \mathrm{O}^{-}$or $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Cl}+\mathrm{CH}_{3} \mathrm{OH}$

Anupa Sharad Medhekar

Anupa Sharad Medhekar

Numerade Educator

Problem 9

a. Which is a better nucleophile, $\mathrm{CH}_{3} \mathrm{OH}$ or $\mathrm{CH}_{3} \mathrm{NH}_{2}$ ?
b. Which is a stronger base?

Anupa Sharad Medhekar

Anupa Sharad Medhekar

Numerade Educator

Problem 10

List the following species in order from best nucleophile to poorest nucleophile:

Anupa Sharad Medhekar

Anupa Sharad Medhekar

Numerade Educator

Problem 11

What is the product of the reaction of bromoethane with each of the following nucleophiles?
a. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{O}^{-}$
b. $\mathrm{CH}_{3} \mathrm{C} \equiv \mathrm{C}^{-}$
c. $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{~N}$
d. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{~S}^{-}$

Madeline Currie

Madeline Currie

Numerade Educator

Problem 12

Draw the substitution products that will be formed from the following $S_{N} 1$ reactions:
a. 3-chloro-3-methylhexane and methanol
b. 3-bromo-3-methylpentane and methanol

Anupa Sharad Medhekar

Anupa Sharad Medhekar

Numerade Educator

Problem 13

Arrange the following alkyl halides in order from most reactive to least reactive in an $\mathrm{S}_{\mathrm{N}} 1$ reaction: 2-bromo-2-methylpentane, 2-chloro-2-methylpentane, 3-chloropentane, and 2-iodo-2-methylpentane.

Anupa Sharad Medhekar

Anupa Sharad Medhekar

Numerade Educator

Problem 14

Draw the configuration(s) of the substitution product(s) that will be formed from the
a. $S_{N} 2$ reaction of each of the following compounds with the indicated nucleophile:b. $S_{N} 1$ reaction of each of the following compounds with the indicated nucleophile:

Madeline Currie

Madeline Currie

Numerade Educator

Problem 15

Which of the following reactions will go faster if the concentration of the nucleophile is increased?

Allison Krajewski

Allison Krajewski

Numerade Educator

Problem 16

After a proton is removed from the OH group, which compound in each pair would form a cyclic ether more rapidly?

Madeline Currie

Madeline Currie

Numerade Educator

Problem 17

Draw the product of each of the following intramolecular reactions:

Madeline Currie

Madeline Currie

Numerade Educator

Problem 18

What would be the major elimination product obtained from the E2 reaction of each of the following alkyl halides with hydroxide ion?

Anupa Sharad Medhekar

Anupa Sharad Medhekar

Numerade Educator

Problem 19

a. What is the major product formed when the following compounds undergo an E1 reaction?
1.
<smiles>CCC(C)C(C)(Br)CC</smiles>
3.
<smiles>CCC(C)(I)c1ccc(C)cc1</smiles>
$2 .$
<smiles>CCCC(C)(C)Cl</smiles>
$4 .$
<smiles>CC1(Cl)CCCCC1</smiles>
b. What is the major product formed when the compounds undergo an E2 reaction?

Narayan Hari

Numerade Educator

Problem 20

a. Which alkyl halide would you expect to be more reactive in an E2 reaction?
b. Which would be more reactive in an E1 reaction?

Anupa Sharad Medhekar

Anupa Sharad Medhekar

Numerade Educator

Problem 21

Which of the following compounds would react faster in an
a. E1 reaction?
b. E2 reaction?
c. $\mathrm{S}_{\mathrm{N}} 1$ reaction?
d. $\mathrm{S}_{\mathrm{N}} 2$ reaction?

Madeline Currie

Madeline Currie

Numerade Educator

Problem 22

Why do the $S_{N} 1 / E 1$ reactions of tertiary alkyl halides favor the substitution product?

Joshua Gibson

Numerade Educator

Problem 23

$$
\text { a. Which reacts faster in an } \mathrm{S}_{\mathrm{N}} 2 \text { reaction? }
$$b. Which reacts faster in an $E 1$ reaction?c. Which reacts faster in an $S_{N} 1$ reaction?

Anupa Sharad Medhekar

Anupa Sharad Medhekar

Numerade Educator

Problem 24

Indicate whether the specified alkyl halides will form primarily substitution products, only elimination products, both substitution and elimination products, or no products when they react with sodium methoxide.
a. 1-bromobutane
c. 2-bromobutane
b. 1-bromo-2-methylpropane
d. 2-bromo-2-methylpropane

Grigoriy Sereda

Grigoriy Sereda

Numerade Educator

Problem 25

Amines are good nucleophiles, even though they are neutral molecules. How would the rate of an $\mathrm{S}_{\mathrm{N}} 2$ reaction between an amine and an alkyl halide be affected if the polarity of the solvent is increased?

Madeline Currie

Madeline Currie

Numerade Educator

Problem 26

How will the rate of each of the following $\mathrm{S}_{\mathrm{N}} 2$ reactions change if it is carried out in a more polar solvent?
a. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}+\mathrm{HO}^{-} \longrightarrow \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}+\mathrm{Br}^{-}$
b.
c. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{I}+\mathrm{NH}_{3} \longrightarrow \mathrm{CH}_{3} \mathrm{CH}_{2}+\mathrm{NH}_{3} \mathrm{I}^{-}$

Anupa Sharad Medhekar

Anupa Sharad Medhekar

Numerade Educator

Problem 27

Which reaction in each of the following pairs will take place more rapidly?
a. $\mathrm{CH}_{3} \mathrm{Br}+\mathrm{HO}^{-} \longrightarrow \mathrm{CH}_{3} \mathrm{OH}+\mathrm{Br}^{-}$
$\mathrm{CH}_{3} \mathrm{Br}+\mathrm{H}_{2} \mathrm{O} \longrightarrow \mathrm{CH}_{3} \mathrm{OH}+\mathrm{HBr}$
b. $\mathrm{CH}_{3} \mathrm{I}+\mathrm{HO}^{-} \longrightarrow \mathrm{CH}_{3} \mathrm{OH}+\mathrm{I}^{-}$
$\mathrm{CH}_{3} \mathrm{Cl}+\mathrm{HO}^{-}-\mathrm{CH}_{3} \mathrm{OH}+\mathrm{Cl}^{-}$
c. $\mathrm{CH}_{3} \mathrm{Br}+\mathrm{NH}_{3} \longrightarrow \mathrm{CH}_{3} \stackrel{+}{N H}_{3}+\mathrm{Br}^{-}$
$\mathrm{CH}_{3} \mathrm{Br}+\mathrm{H}_{2} \mathrm{O} \longrightarrow \mathrm{CH}_{3} \mathrm{OH}+\mathrm{HBr}$
d. $\mathrm{CH}_{3} \mathrm{Br}+\mathrm{HO}^{-} \stackrel{\text { DMSO }}{\longrightarrow} \mathrm{CH}_{3} \mathrm{OH}+\mathrm{Br}^{-}$
$\mathrm{CH}_{3} \mathrm{Br}+\mathrm{HO}^{-} \stackrel{\text { EtOH }}{\longrightarrow} \mathrm{CH}_{3} \mathrm{OH}+\mathrm{Br}^{-}$
e. $\mathrm{CH}_{3} \mathrm{Br}+\mathrm{NH}_{3} \stackrel{\text { DMSO }}{\longrightarrow} \mathrm{CH}_{3}+\stackrel{+}{\mathrm{NH}_{3}}+\mathrm{Br}^{-}$
$\mathrm{CH}_{3} \mathrm{Br}+\mathrm{NH}_{3} \stackrel{\text { EtOH }}{\longrightarrow} \mathrm{CH}_{3}+{\mathrm{NH}_{3}}+\mathrm{Br}^{-}$

Anupa Sharad Medhekar

Anupa Sharad Medhekar

Numerade Educator

Problem 28

Most of the $\mathrm{p} K_{\mathrm{a}}$ values given in this text have been determined in water. How would the $\mathrm{p} K_{\mathrm{a}}$ value of a carboxylic acid change if it were determined in a solvent less polar than water?

Anupa Sharad Medhekar

Anupa Sharad Medhekar

Numerade Educator

Problem 29

a. In which solvent would tert-butyl bromide undergo an $\mathrm{S}_{\mathrm{N}} 1$ reaction more rapidly: $50 \%$ water and $50 \%$ ethanol or $100 \%$ ethanol?
b. How would the products differ in the two solvents?

Madeline Currie

Madeline Currie

Numerade Educator

Problem 30

What would be the best way to prepare the following ethers using an alkyl halide and an alcohol?
a. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CHOCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}$
b. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OCH}_{2} \mathrm{CHCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}$
c.
<smiles>COC1CCCCC1</smiles>

Anupa Sharad Medhekar

Anupa Sharad Medhekar

Numerade Educator

Problem 31

Which reaction in each of the following pairs will take place more rapidly?
a. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Cl}+\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH} \longrightarrow \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OCH}_{2} \mathrm{CH}_{3}+\mathrm{HCl}$
b. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Br}+\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH} \longrightarrow \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OCH}_{2} \mathrm{CH}_{3}+\mathrm{HBr}$ $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Cl}+\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH} \longrightarrow \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OCH}_{2} \mathrm{CH}_{3}+\mathrm{HCl}$
c. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{I}+\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2} \longrightarrow \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}+\mathrm{I}^{-}$ $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{I}+\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH} \longrightarrow \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OCH}_{2} \mathrm{CH}_{3}+\mathrm{HI}$

Anupa Sharad Medhekar

Anupa Sharad Medhekar

Numerade Educator

Problem 32

Give the product of the reaction of ethyl chloride with each of the following nucleophiles:
a. $\mathrm{HO}^{-}$
b. $\mathrm{NHCH}_{3}$
c. $\mathrm{H}_{2} \mathrm{O}$
d. $\mathrm{CH}_{3} \mathrm{~S}^{-}$
e. $\mathrm{CH}_{3} \mathrm{O}^{-}$
f. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{NH}_{2}$

Anupa Sharad Medhekar

Anupa Sharad Medhekar

Numerade Educator

Problem 33

Which is a better nucleophile?
a. $\mathrm{H}_{2} \mathrm{~S}$ or $\mathrm{HS}^{-}$
b. $\mathrm{CH}_{3} \mathrm{NH}_{2}$ or $\mathrm{CH}_{3} \mathrm{OH}$

Anupa Sharad Medhekar

Anupa Sharad Medhekar

Numerade Educator

Problem 34

For each of the pairs in Problem 33 , indicate which is a better leaving group.

Gul Rukhsar

Numerade Educator

Problem 35

What nucleophiles could be used to react with propyl iodide to prepare the following compounds?

George Bennett

Numerade Educator

Problem 36

Which alkyl halide in each pair would you expect to be more reactive in an $\mathrm{S}_{\mathrm{N}} 2$ reaction with a given nucleophile?

Allison Krajewski

Allison Krajewski

Numerade Educator

Problem 37

Explain how the following changes would affect the rate of the substitution reaction of 1-bromobutane with methoxide ion in DMF.
a. The concentration of both the alkyl halide and the
c. The nucleophile is changed to ethanol.
nucleophile are tripled.
d. The alkyl halide is changed to 1-chlorobutane.
b. The solvent is changed to ethanol.
e. The alkyl halide is changed to 2 -bromobutane.

Susan Hallstrom

Susan Hallstrom

Numerade Educator

Problem 38

Explain how the following changes would affect the rate of the substitution reaction of 2-bromo-2-methylbutane with methanol: a. The alkyl halide is changed to 2 -chloro-2-methylbutane.
b. The nucleophile is changed to ethanol.

Madeline Currie

Madeline Currie

Numerade Educator

Problem 39

Draw the major product obtained when each of the following alkyl halides undergoes an E2 reaction:

Madeline Currie

Madeline Currie

Numerade Educator

Problem 40

Which alkyl halide in Problem 39 can undergo an E1 reaction? What would be the major product?

Madeline Currie

Madeline Currie

Numerade Educator

Problem 41

For each of the following reactions, give the substitution products; if the products can exist as stereoisomers, show what stereoisomers are obtained:
a. $(R)$-2-bromopentane + high concentration of $\mathrm{CH}_{3} \mathrm{O}^{-}$
d. $(R)-3$-bromo-3-methylhexane $+\mathrm{CH}_{3} \mathrm{OH}$
b. trans-1-bromo-4-methylcyclohexane $+$ high concentration of $\mathrm{CH}_{3} \mathrm{O}^{-} \quad$ e. 1-bromo-1-methylcyclohexane $+\mathrm{CH}_{3} \mathrm{OH}$
c. 3-bromo-3-methylpentane $+\mathrm{CH}_{3} \mathrm{OH}$

Madeline Currie

Madeline Currie

Numerade Educator

Problem 42

Starting with an alkyl halide, how could the following compounds be prepared?
a. 2-methoxybutane
b. 1-methoxybutane
c. dicyclohexyl ether

Anupa Sharad Medhekar

Anupa Sharad Medhekar

Numerade Educator

Problem 43

Which reactant in each of the following pairs will undergo an elimination reaction more rapidly?
a. $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CCl} \stackrel{\mathrm{HO}^{-}}{\stackrel{\mathrm{H}_{2} \mathrm{O}}{\longrightarrow}}$ or $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CI} \stackrel{\mathrm{HO}^{-}}{\stackrel{\mathrm{H}_{2} \mathrm{O}}{\longrightarrow}}$
b. $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CBr} \stackrel{\mathrm{HO}^{-}}{\stackrel{\mathrm{H}_{2} \mathrm{O}}{\longrightarrow}}$ or $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHBr} \frac{\mathrm{HO}^{-}}{\mathrm{H}_{2} \mathrm{O}}$

Anupa Sharad Medhekar

Anupa Sharad Medhekar

Numerade Educator

Problem 44

Give the major product obtained when each of the following alkyl halides undergoes an E2 reaction:
$$
\mathrm{H}_{3} \mathrm{C}
$$

Anupa Sharad Medhekar

Anupa Sharad Medhekar

Numerade Educator

Problem 45

What stereoisomer would be obtained in greater yield when each of the following alkyl halides undergoes an E2 reaction:
a.
<smiles>CCC(C)Br</smiles>
b.
<smiles>CCCC(Cl)CC</smiles>

Hitendra Singh

Numerade Educator

Problem 46

For each of the following reactions, give the major elimination product; if the product can exist as stereoisomers, indicate which stereoisomer is obtained in greater yield:
a. $(R)-2$-bromohexane $+$ high concentration of $\mathrm{HO}^{-}$
c. 3 -bromo-3-methylpentane $+$ high concentration of $\mathrm{HO}^{-}$
b. $(R)-3$-bromo-2,3-dimethylpentane $+$ high concentration of $\mathrm{HO}^{-}$
d. 3-bromo-3-methylpentane $+\mathrm{H}_{2} \mathrm{O}$

Madeline Currie

Madeline Currie

Numerade Educator

Problem 47

Starting with bromocyclohexane, how could the following compounds be prepared?

Zubair Abdulla

Numerade Educator

Problem 47

Starting with bromocyclohexane, how could the following compounds be prepared?

Zubair Abdulla

Numerade Educator

Problem 48

Which stereoisomer would be obtained in greater yield from an E2 reaction of each of the following alkyl halides?

Grigoriy Sereda

Grigoriy Sereda

Numerade Educator

Problem 48

Which stereoisomer would be obtained in greater yield from an E2 reaction of each of the following alkyl halides?

Grigoriy Sereda

Grigoriy Sereda

Numerade Educator

Problem 49

Fill in the blanks in the following chemical equations:

Anupa Sharad Medhekar

Anupa Sharad Medhekar

Numerade Educator

Problem 50

For each of the following alkyl halides, indicate what stereoisomer would be obtained in greatest yield if it reacts with a high concentration of ethoxide ion.
a. 3 -bromo- $2,2,3$-trimethylpentane
c. 3 -bromo-2,3-dimethylpentane
b. 4 -bromo $-2,2,3,3$-tetramethylpentane
d. 3 -bromo- 3,4 -dimethylhexane

Madeline Currie

Madeline Currie

Numerade Educator

Problem 51

Alkylbenzyldimethyl ammonium chloride is a leave-on skin antiseptic used to treat such things as cuts and cold sores. It is also the antiseptic in many hand sanitizers. It is actually a mixture of compounds that differ in the number of carbons (any even number between 8 and 18 ) in the alkyl group. Show three different sets of reagents (each set composed of an alkyl chloride and an amine) that can be used to synthesize the alkylbenzyldimethyl ammonium chloride shown here.

Madeline Currie

Madeline Currie

Numerade Educator

Problem 52

a. Explain why 1-bromo-2,2-dimethylpropane has difficulty undergoing either $\mathrm{S}_{\mathrm{N}} 2$ or $\mathrm{S}_{\mathrm{N}} 1$ reactions.
b. Can it undergo E2 and E1 reactions?

Grigoriy Sereda

Grigoriy Sereda

Numerade Educator

Problem 53

An ether can be prepared by an $\mathrm{S}_{\mathrm{N}} 2$ reaction of an alkyl halide with an alkoxide ion ( $\left.\mathrm{RO}^{-}\right)$. Which set of alkyl halide and alkoxide ion would give you a better yield of cyclopentyl methyl ether?

Anupa Sharad Medhekar

Anupa Sharad Medhekar

Numerade Educator

Problem 54

Give two sets of reactants (each set including an alkyl halide and a nucleophile) that could be used to synthesize the following ether:
<smiles>CCOCCC(C)C</smiles>

Anupa Sharad Medhekar

Anupa Sharad Medhekar

Numerade Educator

Problem 55

Show how the following compounds could be synthesized using the given starting materials:
$$
\mathrm{H}_{3} \mathrm{C}
$$

Anupa Sharad Medhekar

Anupa Sharad Medhekar

Numerade Educator

Problem 56

Indicate which of the compounds will give a higher substitution-product to elimination-product ratio when it reacts with isopropyl bromide: ethoxide ion or tert-butoxide ion.

Anupa Sharad Medhekar

Anupa Sharad Medhekar

Numerade Educator

Problem 57

Which alkyl halide undergoes an E1 reaction more rapidly?

Anupa Sharad Medhekar

Anupa Sharad Medhekar

Numerade Educator

Problem 58

Draw the structures of the products obtained from the following reaction:

Madeline Currie

Madeline Currie

Numerade Educator

Problem 59

cis-4-Bromocyclohexanol and trans-4-bromocyclohexanol form the same elimination product but a different substitution product when they react with $\mathrm{HO}^{-}$.a. Why do they form the same elimination product?
b. Explain, by showing the mechanisms, why different substitution products are obtained.
c. How many stereoisomers does each of the elimination and substitution reactions form?

Banhishikha Sinha

Banhishikha Sinha

Numerade Educator

Problem 60

A cyclic compound can be formed by an intramolecular reaction. Draw the structure of the ether that would be formed from each of the following intramolecular reactions.
a. $\mathrm{BrCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{O}^{-} \longrightarrow$ ether
b. $\mathrm{ClCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{O}^{-} \longrightarrow$ ether

Anupa Sharad Medhekar

Anupa Sharad Medhekar

Numerade Educator

Problem 61

Which of the following is more reactive in an E2 reaction?

Madeline Currie

Madeline Currie

Numerade Educator

Problem 62

Draw the elimination products obtained under E2 conditions for each of the following alkyl halides, indicating major and minor products.

Anupa Sharad Medhekar

Anupa Sharad Medhekar

Numerade Educator

Problem 63

a. Identify the substitution products that form when 2 -bromo $-2$-methylpropane is dissolved in a mixture of $80 \%$ ethanol and $20 \%$ water.
b. Explain why the same products are obtained when 2-chloro-2-methylpropane is dissolved in a mixture of $80 \%$ ethanol and $20 \%$ water.

Madeline Currie

Madeline Currie

Numerade Educator

Problem 64

The rate of the reaction of methyl iodide with quinuclidine was measured and then the rate of the reaction of methyl iodide with triethylamine was measured in the same solvent. The concentration of the reagents was the same in both experiments.
a. Which reaction was faster?
b. Which reaction had the larger rate constant?

Allison Krajewski

Allison Krajewski

Numerade Educator

Problem 65

In which solvent-ethanol or diethyl ether-would the equilibrium for the following $S_{\mathrm{N}} 2$ reaction lie farther to the right?

Madeline Currie

Madeline Currie

Numerade Educator

Problem 66

The $\mathrm{p} K_{\mathrm{a}}$ of acetic acid in water is $4.76 .$ What effect would a decrease in the polarity of the solvent have on the p $K_{\mathrm{a}}$ ? Why?

Madeline Currie

Madeline Currie

Numerade Educator

Problem 67

a. Propose a mechanism for the following reaction?
b. Explain why two products are formed.
c. Explain why methanol substitutes for only one of the bromines.

Madeline Currie

Madeline Currie

Numerade Educator