Textbook Question
Predict the product of the following substitution reactions, paying close attention to the stereochemical outcome of the reactions.
(b)
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7. Substitution Reactions
Substitution Comparison
2:11 minutesProblem 82c,d
Textbook Question
Fill in the squares in the following chemical equations:
c. 
d. 
Verified step by step guidance1
Step 1: Analyze the first reaction. The starting material is cyclohexyl chloride (C6H11Cl), and the product is cyclohexyl phenyl ether (C6H11-O-C6H5). This suggests that the missing reactant in the square is phenol (C6H5OH), which reacts with cyclohexyl chloride in the presence of a base to form the ether.
Step 2: For the first reaction, the mechanism likely involves a nucleophilic substitution (SN2 or SN1) where phenol acts as the nucleophile, attacking the electrophilic carbon attached to the chlorine atom in cyclohexyl chloride.
Step 3: Analyze the second reaction. The product is a substituted cyclohexane with a methyl group and a cyano group (-C≡N) attached. This suggests that the missing reactant in the square is methylcyclohexane (C6H11CH3), which reacts with cyanide ion (CN⁻) in a substitution reaction.
Step 4: For the second reaction, the mechanism likely involves a nucleophilic substitution (SN2) where the cyanide ion attacks the electrophilic carbon in methylcyclohexane, replacing a leaving group (likely a halide such as bromine or chlorine).
Step 5: Ensure that the reaction conditions for both reactions are appropriate. For the first reaction, a base like NaOH or KOH may be required to deprotonate phenol and enhance its nucleophilicity. For the second reaction, polar aprotic solvents like DMSO or acetone may be used to facilitate the SN2 mechanism.
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2mKey Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
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