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Predicting the Mechanism of Nucleophilic Substitution Reactions

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Organic Chemistry 1 Textbook > Nucleophilic Substitutions and Elimination Reactions

Introduction to Substitution Reactions

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Predict which mechanism the following reactions will follow (SN1 or SN2)

a)



b)



c)



d)


More Introduction to Substitution Reactions Questions:
Provide the structures of compounds A-C in the synthetic sequence below:
Rank the following from best to worst in ability to act as a nucleophile
H2O
Cl-
Rate of SN1
Compare the rate of SN1 reactions on the following:
Rate of SN2
Compare the rate of SN2 reactions on these substrates:
Practice Question: Grignard Reactions
Predict the product(s) of the following reactions:
Reaction mechanisms
Provide the structures of compounds A-E:
Reaction mechanisms
Provide the structures of compounds A-C in the synthetic sequence below:
Provide the reagent(s) for the following reactions:
Reaction mechanisms
Provide a mechanism for the following reaction:
Provide the structures of compounds A-E:
Predicting the Mechanism of Nucleophilic Substitution Reactions
Predict which mechanism the following reactions will follow (SN1 or SN2)
a)
b)
Predict the major organic product(s) of the following reactions. Be sure to indicate stereochemistry where appropriate.
Predict the product and draw a mechanism for the reaction below. Make sure to indicate stereochemistry.
For the reaction below, predict the products and draw the mechanism for the reaction
Predict the major organic product(s) of the following reactions. Be sure to indicate stereochemistry where appropriate.
Practice: Nuclophilic Subsitution
A graduate student performs two reactions in order to make some new ethers. In the first reaction the student mixes 3-chloro-2-methylprop-1-ene and methanol and in the second the student mixes 4-chloro-2-methylbut-1-ene with methanol. The next day the student examines the reaction and finds that one has completely finished and the other is not even 10% complete. Which reaction has completely finished? Why?
Structure determination
A molecule A (CH3)3CH2CH2Br) was treated with aqueous NaOH to form B. Compound B was treated with H2SO4 and heated to form C. Product C was reacted with Bromine under dry conditions to yield D. Product D has four possible isomers however 2 are favoured. Draw the structures of A-D and the 2 major stereoisomers of D.
Reaction Mechanisms: Synthesis
Design two syntheses, questions 1 and 2 from the indicated starting material. In addition, you can to use any hydrocarbon with three or fewer carbon atoms, any solvents or inorganic reagents, and any organic reagents that do not contribute carbon atoms to the carbon skeleton in the product. More than one step will be required for each synthesis. Show the required reagents and the product of each step but not the mechanisms.
Reaction mechanisms: Substitution reactions
Predict the product(s) of the following reaction.
Substitution reactions
The reaction below probably proceeds by what type of mechanism
Reaction Mechanisms
Use curly arrows to show the mechanisms for the following two questions.
Reaction mechanisms: Provide the product
Predict the product(s) of the following reactions:
Fill in the blanks of the following reactions
1)
2)
Provide reagents for the following reactions:
Reaction mechanisms: Predict the product
Predict the product and propose a mechanism for the following reaction:
Substitution reactions: Nucleophiles
Rank the following from best to worst in ability to act as a nucleophile
H2O (1), Cl- (2), HO- (3), I- (4)