7. Substitution Reactions
Substitution Comparison
7. Substitution Reactions
Substitution Comparison - Video Tutorials & Practice Problems
On a tight schedule?
Get a 10 bullets summary of the topicHow can we tell which mechanism to use? This question will get more complicated unfortunately, but for now we can use the following factors to answer this question.
1
concept
How do we predict if the mechanism is SN1 or SN2?
Video duration:
3mPlay a video:
When given a substitution reaction, use the following two factors to determine the mechanism:
Nucleophile Strength: SN1 = WEAK SN2 = STRONG
Leaving Group Substitution: SN1 = 3° > 2° SN2 = 0° > 1° > 2°
2
Problem
ProblemPredict the product of the reaction
A
B
C
D
3
Problem
ProblemPredict the product of the reaction
A
B
C
D
Do you want more practice?
We have more practice problems on Substitution Comparison
Additional resources for Substitution Comparison
PRACTICE PROBLEMS AND ACTIVITIES (89)
- Give two syntheses for (CH3)2CH—O—CH2CH3, and explain which synthesis is better.
- Show how each compound might be synthesized by the SN2 displacement of an alkyl halide. e. H2C=CH—CH2CN f. H—...
- Show how you might use SN2 reactions to convert 1-chlorobutane into the following compounds. e. CH3—(CH2)3—C≡...
- Show how you might use SN2 reactions to convert 1-chlorobutane into the following compounds. c. 1-iodobutane ...
- Under certain conditions, the reaction of 0.5 M 1-bromobutane with 1.0 M sodium methoxide forms 1-methoxybutan...
- In contrast, optically active butan-2-ol does not racemize on treatment with a solution of KOH. Explain why a ...
- For each reaction, give the expected substitution product, and predict whether the Âmechanism will be predomin...
- The reaction of an amine with an alkyl halide gives an ammonium salt. R3N amine + R'—X alkyl halide —> R3(...
- Explain why the following alkyl halide does not undergo a substitution reaction, regardless of the base that i...
- Starting with an alkyl halide, how could the following compounds be prepared? c. butylmethylamine
- The rate of the reaction of methyl iodide with quinuclidine was measured in nitrobenzene, and then the rate of...
- The rate of the reaction of methyl iodide with quinuclidine was measured in nitrobenzene, and then the rate of...
- Two bromoethers are obtained from the reaction of the following alkyl dihalide with methanol. Draw the structu...
- Starting with an alkyl halide, how could the following compounds be prepared? b. 1-methoxybutane
- Starting with an alkyl halide, how could the following compounds be prepared? a. 2-methoxybutane
- What nucleophiles would form the following compounds as a result of reacting with 1-iodobutane? h.
- What nucleophiles would form the following compounds as a result of reacting with 1-iodobutane? g.
- Which substitution reaction takes place more rapidly? d. CH3CH2Cl + I− or CH3CH2Br + I−
- Which substitution reaction takes place more rapidly? c. CH3CH2Cl + CH3O− or (in ethanol) CH3CH2Cl + CH3S−
- Which substitution reaction takes place more rapidly? b.
- Which substitution reaction takes place more rapidly? a. CH3CH2Br + H2O or CH3CH2Br + HO−
- Explain why tetrahydrofuran can solvate a positively charged species better than diethyl ether can.
- Which reaction in each of the following pairs takes place more rapidly? (EtOH is ethyl alcohol; Et2O is diethy...
- How will the rate of each of the following SN2 reactions change if it is carried out in a more polar solvent? ...
- Amines are good nucleophiles, even though they are neutral. How would the rate of an SN2 reaction between an a...
- Draw the substitution products for each of the following reactions; if the products can exist as stereoisomers...
- Draw the substitution products for each of the following reactions; if the products can exist as stereoisomers...
- Propose a mechanism for the following reaction:
- a. Identify the substitution products that form when 2-bromo-2-methylpropane is dissolved in a mixture of 80% ...
- What stereoisomers do the following reactions form? b.
- What stereoisomers do the following reactions form? d.
- What stereoisomers do the following reactions form? c.
- What stereoisomers do the following reactions form? a.
- What is the major product of each of the following reactions? d.
- What is the major product of each of the following reactions? c.
- What is the major product of each of the following reactions? b.
- What is the major product of each of the following reactions? a.
- Would the following nucleophiles be more likely to participate in an Sâ‚™1 or Sâ‚™2 reaction? (b)
- Would the following nucleophiles be more likely to participate in an Sâ‚™1 or Sâ‚™2 reaction? (d)
- For each solvent, indicate the most likely substitution reaction to take place. (b)
- For each solvent, indicate the most likely substitution reaction to take place. (d)
- For each solvent, indicate the most likely substitution reaction to take place. (f)
- (•••) Give a mechanism for the following substitution and elimination reactions. (a)
- Suggest a mechanism for the following substitution reactions. (a)
- Suggest a mechanism for the following substitution reactions. (b)
- Would you expect the following conditions to favor Sâ‚™1 or Sâ‚™2? (d)
- Would you expect the following conditions to favor Sâ‚™1 or Sâ‚™2? (a)
- Predict the product of the substitution reactions, paying attention to the stereochemical outcome. (a)
- Predict the product of the substitution reactions, paying attention to the stereochemical outcome. (d)
- Predict the product of the following substitution reactions, making sure to note whether a rearrangement shoul...
- (•) Suggest a mechanism for the following substitution reactions. (b)
- (••) Predict the product of the following substitution reactions, paying close attention to the stereochemical...
- (••) Predict the product of the following substitution reactions, paying close attention to the stereochemical...
- (••••) Which of the following substitution reactions would you expect to occur more quickly? Explain your answ...
- Which reaction would be faster, the one with DMSO as the solvent or the one with ethanol (EtOH)?
- Predict the product of the substitution reactions, paying attention to the stereochemical outcome.(b) <IMAG...
- (•••) Crown ethers are able to solvate cations based on their size. Specifically, 15-crown-5 forms stable comp...
- To solve this problem, you need to read the description of the Hammett s, r treatment given in . When the ra...
- Write the mechanism for the reaction of a cysteine side chain with iodoacetic acid.
- 2-Acetoxycyclohexyl tosylate reacts with acetate ion to form 1,2-cyclohexanediol diacetate. The reaction is st...
- 2-Acetoxycyclohexyl tosylate reacts with acetate ion to form 1,2-cyclohexanediol diacetate. The reaction is st...
- 2-Acetoxycyclohexyl tosylate reacts with acetate ion to form 1,2-cyclohexanediol diacetate. The reaction is st...
- Predict the product for the following substitution reactions. Indicate whether each reaction likely proceeds b...
- Predict the product for the following substitution reactions. Indicate whether each reaction likely proceeds b...
- (••) Predict the product(s) of the following reactions. (h)
- (••) LOOKING BACK The benzylic bromide shown undergoes neither SN1 nor SN2 substitution reactions. Explain.
- Predict the product for the following substitution reactions. Indicate whether each reaction likely proceeds b...
- Would you expect the following substitution reaction to proceed with inversion or racemization? Why?
- Predict the product of the following substitution reactions, making sure to note whether a rearrangement shoul...
- (••) Predict the product of the following substitution reactions, paying close attention to the stereochemical...
- (•••) Give a mechanism for the following substitution and elimination reactions.(c) <IMAGE>
- Would the following nucleophiles be more likely to participate in an Sâ‚™1 or Sâ‚™2 reaction?(c) <IMAGE>
- For each solvent, indicate the most likely substitution reaction to take place.(a) <IMAGE>
- For each solvent, indicate the most likely substitution reaction to take place.(e) <IMAGE>
- Would you expect the following conditions to favor Sâ‚™1 or Sâ‚™2?(b) <IMAGE>
- Predict the product of the following substitution reactions, making sure to note whether a rearrangement shoul...
- Predict the product of the following substitution reactions, making sure to note whether a rearrangement shoul...
- (•) Suggest a mechanism for the following substitution reactions.(c) <IMAGE>
- (•) Suggest a mechanism for the following substitution reactions.(d) <IMAGE>
- (••) Predict the product of the following substitution reactions, paying close attention to the stereochemical...
- Would the following nucleophiles be more likely to participate in an Sâ‚™1 or Sâ‚™2 reaction?(a) <IMAGE>
- Would the following nucleophiles be more likely to participate in an Sâ‚™1 or Sâ‚™2 reaction?(f) <IMAGE>
- For each solvent, indicate the most likely substitution reaction to take place.(g) <IMAGE>
- (••) Predict the product of the following substitution reactions, paying close attention to the stereochemical...
- (••) Predict the product of the following substitution reactions, paying close attention to the stereochemical...
- Would the following nucleophiles be more likely to participate in an Sâ‚™1 or Sâ‚™2 reaction?(e) <IMAGE>
- Fill in the squares in the following chemical equations:c. <IMAGE>d. <IMAGE>
- a. Propose a mechanism for the following reaction.<IMAGE>
- Draw the substitution and elimination products.a. <IMAGE>b. <IMAGE>