7. Substitution Reactions
Substitution Comparison
7. Substitution Reactions
Substitution Comparison - Video Tutorials & Practice Problems
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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.
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concept
How do we predict if the mechanism is SN1 or SN2?
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Video transcript
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°
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Problem
ProblemPredict the product of the reaction
A
B
C
D
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Problem
ProblemPredict the product of the reaction
A
B
C
D
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Additional resources for Substitution Comparison
PRACTICE PROBLEMS AND ACTIVITIES (110)
- For each reaction, give the expected substitution product, and predict whether the mechanism will be predomin...
- Explain why the following alkyl halide does not undergo a substitution reaction, regardless of the base that i...
- 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:
- What stereoisomers do the following reactions form? b.
- 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 Sₙ1 or Sₙ2 reaction? (b)
- Would the following nucleophiles be more likely to participate in an Sₙ1 or Sₙ2 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 Sₙ1 or Sₙ2? (d)
- Would you expect the following conditions to favor Sₙ1 or Sₙ2? (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...
- 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...
- 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 Sₙ1 or Sₙ2 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 Sₙ1 or Sₙ2?(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 Sₙ1 or Sₙ2 reaction?(a) <IMAGE>
- Would the following nucleophiles be more likely to participate in an Sₙ1 or Sₙ2 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 Sₙ1 or Sₙ2 reaction?(e) <IMAGE>
- Fill in the squares in the following chemical equations:a. <IMAGE>b. <IMAGE>
- Fill in the squares in the following chemical equations:c. <IMAGE>d. <IMAGE>
- What substitution products are obtained when each of the following compounds is added to a solution of sodium ...
- Draw the substitution products for each of the following reactions. If the products can exist as stereoisomer...
- Draw the substitution products for each of the following reactions. If the products can exist as stereoisomer...
- a. Propose a mechanism for the following reaction.<IMAGE>
- Draw the substitution and elimination products.a. <IMAGE>b. <IMAGE>
- What nucleophiles would form the following compounds as a result of reacting with 1-iodobutane?a. <IMAGE>...
- What nucleophiles would form the following compounds as a result of reacting with 1-iodobutane?e. <IMAGE>...
- Aldolase shows no activity if it is incubated with iodoacetic acid before fructose-1,6-bisphosphate is added t...
- Predict the major products of the following substitutions.a. ethyl bromide CH3CH2Br + potassium tert-butoxide ...
- Predict the major products of the following substitutions.f. 1-chloropentane + KF 18-crown-6 CH3CN —>
- Chlorocyclohexane reacts with sodium cyanide (NaCN) in ethanol to give cyanocyclohexane. The rate of formation...
- Draw perspective structures or Fischer projections for the substitution products of the following reactions.(b...
- Optically active 2-bromobutane undergoes racemization on treatment with a solution of KBr. a. Give a mechanism...
- For each reaction, give the expected substitution product, and predict whether the mechanism will be predomin...
- The following reaction takes place under second-order conditions (strong nucleophile), yet the structure of th...
- Using the given starting material, any necessary inorganic reagents and catalysts, and any carbon-containing c...
- For each reaction, give the expected substitution product, and predict whether the mechanism will be predomin...
- Show how you might use SN2 reactions to convert 1-chlorobutane into the following compounds. a. butan-1-ol
- Show how you might use SN2 reactions to convert 1-chlorobutane into the following compounds.b. 1-fluorobutane
- A solution of pure (S)-2-iodobutane([α] = +15.90° ) in acetone is allowed to react with radioactive iodide, 13...
- Show how you would convert (in one or two steps) 1-phenylpropane to the three products shown below.In each cas...
- Using cyclohexane as one of your starting materials, show how you would synthesize the following compounds.(c)...
- Alkylbenzyldimethyl ammonium chloride is a leave-on skin antiseptic used to treat such things as cuts and cold...
- Which reaction in each of the following pairs takes place more rapidly? (EtOH is ethyl alcohol; Et2O is diethy...
- Under which of the following reaction conditions will (R)-1-chloro-1-phenylethane form the most (R)-1-phenyl-1...
- Draw the substitution products for each of the following reactions; if the products can exist as stereoisomers...
- Suggest a reagent to carry out each of the following conversions to an alcohol. (a)
- (••) LOOKING BACK When (R)-(1-bromoethyl)benzene is treated with sodium cyanide, a single enantiomer is produc...
- Order the following molecules on the basis of their nucleophilic strength using the pKₐ values of their conjug...
- Suggest a reagent to carry out each of the following conversions to an alcohol.(c) <IMAGE>
- (••) Predict the product(s) of the following reactions.(f) <IMAGE>
- (••) Predict the product(s) of the following reactions.(g) <IMAGE>
- (••••) When trans-4-bromocyclohexanol is treated with base, an intramolecular substitution reaction occurs to ...
- Which of the following reactions take place more rapidly when the concentration of the nucleophile is increase...
- Starting with (R)-1-deuterio-1-propanol, how could you prepare c. (R)-1-deuterio-1-methoxypropane?
- Even with an excess of cyanide, only one equivalent will react with the following dibromoalkane. To which carb...
- (••••) Suggest a mechanism for the following reactions.(a) Substitution : ...
- (••) Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following ...
- (••) Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following ...
- (••) Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following ...
- Explain how 1-butanol can be converted into the following compounds:a. <IMAGE>
- Explain how 1-butanol can be converted into the following compounds:b. <IMAGE>
- When equivalent amounts of methyl bromide and sodium iodide are dissolved in methanol, the concentration of io...
- Provide an arrow-pushing mechanism that rationalizes the outcome of the reaction shown.<IMAGE>
- Optically active 2-bromobutane undergoes racemization on treatment with a solution of KBr. Propose a mechanism...
- Provide a mechanism for the following Sₙ1 reactions that feature a rearrangement.(b) <IMAGE>
- Suggest a mechanism for the following substitution reactions.(c) <IMAGE>
- (••) Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following ...
- (••) Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following ...
- What stereoisomers does the following reaction form?<IMAGE>
- When tert-butyl bromide is heated with an equal amount of ethanol in an inert solvent, one of the products is ...
- Explain the difference in reactivity between CH3O+H2 and CH3OH in a nucleophilic substitution reaction. (The p...