Alkenes Multi-Step Synthesis Practice Problems
Practice
1.
Provide the structure of the expected major organic product from the following reaction sequence as well as the structure of the intermediate product after each step:
Answer
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Solution
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2.
Answer
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3.
Answer
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4.
Complete the following synthesis by adding the missing reagent(s) for each step and the structures for compound A and B:
Answer
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Solution
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5.
Complete the following synthesis by adding the missing reagent(s) for each step and the structures for compound A and B:
Answer
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Solution
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6.
Complete the following synthesis by adding the missing reagent(s) for each step and the structures for compounds A and B:
Answer
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7.
Complete the following synthesis by adding the missing reagent(s) for each step and the structures for compound A and B:
Answer
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8.
Complete the following synthesis by adding the missing reagent(s) for each step and the structures for compound A and B:
Answer
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9.
a)
Predict the product(s) that are formed after each step for reactions A-G. In each case, consider formation of any chiral center(s) and draw all expected stereoisomers.
This is a comprehensive problem that covers the following topics and will serve as a review of all of them:
Substitution and elimination reactions. Particularly, substitution and elimination reactions of alcohols, the regio– and stereochemistry of E2 reactions and E2 reaction of cyclohexanes.
Mesylation and tosylation in Substitution and elimination reactions.
Hydrohalogenation of alkenes according to the Markovnikov’s rule.
Radical hydrohalogenation of alkenes.
Hydroboration-Oxidation of Alkenes.
Halogenation of alkenes through halohydrin formation.
Syn and anti dihydroxilation of alkenes.
Elimination reactions: Zaitsev and Hoffman products.
Ozonoloysis of Alkenes.
Attempt solving the entire problem before accessing the answers!
The answers will give you the structure of the final product(s) only. Use this as a hint to determine the compounds formed after the first and second reactions.
The structure of intermediate compounds can be found under the Solution tab.
Answer
Answer
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Answer
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Answer
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Answer
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Answer
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Answer
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Solution
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10.
The full Video solution to the problems:
Solution
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11.
Check Also in Addition Reactions of Alkenes
- Electrophilic Addition Reactions to Alkenes
- Markovnikov’s Rule
- Markovnikov’s Rule with Practice Problems
- Addition of Water to Alkenes
- Acid-Catalyzed Hydration of Alkenes with Practice Problems
- Rearrangements in Alkene Addition Reactions
- Oxymercuration-Demercuration
- Addition of Alcohols to Alkenes
- Free-Radical Addition of HBr: Anti-Markovnikov Addition
- Hydroboration-Oxidation: The Mechanism
- Hydroboration-Oxidation of Alkenes: Regiochemistry and Stereochemistry with Practice Problems
- Halogenation of Alkenes and Halohydrin Formation
- The Regiochemistry of Alkene Addition Reactions
- The Stereochemistry of Alkene Addition Reactions
- Cis product in an anti Addition Reaction of Alkenes
- Ozonolysis of Alkenes with Practice Problems
- Syn Dihydroxylation of Alkenes with KMnO4 and OsO4
- Anti Dihydroxylation of Alkenes with MCPBA and Other Peroxides with Practice Problems
- Oxidative Cleavage of Alkenes with KMno4 and O3
- Alkene Reactions Practice Problems
- Changing the Position of a Double Bond
- Changing the Position of a Leaving Group
- Alkene Addition Reactions Practice Quiz