In the previous post we talked about the mechanism, kinetics, reactivity, rearrangements and some more features of the SN1 reaction.
The SN1 Nucleophilic Substitution Reaction
You can go over those before solving the practice problems shown below.
The SN1 Mechanism: Kinetcis, Thermodynamics, Curved Arrows and Stereochemistry with Practice Problems
Practice
1.
What happens to the rate of the SN1 reaction under each of the following changes in the concentration of the substrate (RX) and nucleophile (Nu)?
a) [RX] is doubled, and [Nu] stays the same.
b) Both, [RX] and [Nu] are doubled.
c) [RX] is doubled, and [Nu] is halved.
d) Both, [RX] and [Nu] are tripled.
Answer
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2.
a)
What happens to the rate of the SN1 reaction under each of the following changes in the concentration of the substrate (RX) and nucleophile (Nu)?
a) [Nu] is doubled, and [R-X] stays the same.
b) [Nu] stays the same, and [R-X] is doubled.
c) [Nu] is doubled, and [R-X] is halved.
d) [R-X] is tripled, and [Nu] is halved.
Answer
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3.
a)
Consider the energy diagram for the following reaction:
a) Label the electrophile and the nucleophile.
b) Does the reaction proceed via SN1 or SN2 mechanism?
c) Draw the products and complete mechanism of the reaction and identify the rate-determining step.
d) Is there an intermediate in this reaction? If yes, show its structure and position on the energy diagram.
e) How many kJ is the activation energy of the rate-determining step?
f) Label the transition state(s)
g) Is the reaction endothermic or exothermic?
h) How many kJ is the ΔG° of the reaction?
i) What is the rate law equation of the reaction?
j) Is the overall rate of the reaction first order or second order?
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4.
a)
Label each energy diagram as exothermic or endothermic and indicate if it goes through SN1 or SN2 mechanism:
Answer
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5.
Classify the following carbocations from the least to most stable:
Answer
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6.
Identify which of the following compounds will, under appropriate conditions, undergo an SN1 reaction and arrange them from the least to most reactive in SN1 reactions:
Answer
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7.
a)
For each pair, determine the compound that reacts faster in SN1 hydrolysis with water. Draw the major product for each hydrolysis reaction.
Answer
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8.
The rate of SN1 reactions increases in polar aprotic solvents.
True, False
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9.
Choose the polar protic solvents and highlight the hydrogen atom that makes them protic:
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10.
Which of the following solvents would be the best option to facilitate the ionization of 2-bromo-2-methylbutane?
Answer
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11.
Which solvent favors SN1 and which solvent favors SN2 nucleophilic substitution reaction?
Answer
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12.
For each reaction, select the better solvent to perform an SN1 substitution and draw the structure of the final product.
Answer
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13.
a)
Draw the mechanism and show the products with the correct stereochemistry for the following SN1 reactions:
Answer
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Solution
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14.
Draw the structure of carbocation intermediates forming upon ionization. Where possible, include resonance structures and rearrangements:
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15.
a)
Show how each carbocation can become more stable via a 1,2-hydride or 1,2-alkyl shift rearrangement:
Answer
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16.
Draw a possible mechanism for each of the following substitution reactions:
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17.
The following alkyl halide gives several different products when heated in ethanol. Draw curved arrow mechanisms to explain how the following four products are formed.
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18.
Propose a mechanism for the following reaction:
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19.
a)
Purpose a plausible curved arrow mechanism for the formation of each product in the following reaction:
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20.
Purpose a plausible curved arrow mechanism for the formation of each product in the following reaction:
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21.
Check Also
- Introduction to Alkyl Halides
- Nomenclature of Alkyl Halides
- Nucleophilic Substitution Reactions – An Introduction
- All You Need to Know About the SN2 Reaction Mechanism
The SN2 Mechanism: Kinetics, Thermodynamics, Curved Arrows, and Stereochemistry with Practice Problems - The Stereochemistry of SN2 Reactions
- The SN1 Nucleophilic Substitution Reaction
- Reactions of Alkyl Halides with Water
- The Stereochemistry of SN1 Reaction Mechanism
- The SN1 Mechanism: Kinetics, Thermodynamics, Curved Arrows, and Stereochemistry with Practice Problems
- The Substrate and Nucleophile in SN2 and SN1 Reactions
- Carbocation Rearrangements in SN1 Reactions with Practice Problems
- Ring Expansion Rearrangements
- Ring Contraction Rearrangements
- When Is the Mechanism SN1 or SN2?
- Reactions of Alcohols with HCl, HBr, and HI Acids
- SOCl2 and PBr3 for Conversion of Alcohols to Alkyl Halides
- Alcohols in Substitution Reactions with Tons of Practice Problems
- How to Choose Molecules for Doing SN2 and SN1 Synthesis-Practice Problems
- Exceptions in SN2 and SN1 Reactions
- Nucleophilic Substitution and Elimination Practice Quiz
- Reactions Map of Alkyl Halides