Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

14. Synthetic Techniques

Retrosynthesis

Organic Chemistry

14. Synthetic Techniques

Retrosynthesis

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5:30 minutes

Problem 58c

Textbook Question

For each synthesis, start with bromocyclohexane and predict the products. Assume that an excess of each reactant is added so that all possible reactions that can happen will happen.
(c)

Verified step by step guidance

Step 1: Analyze the first reaction. Bromocyclohexane reacts with KOH in ethanol under heat (Δ). This is an elimination reaction where KOH acts as a base, removing a β-hydrogen from bromocyclohexane. The result is the formation of cyclohexene (compound A) via an E2 mechanism.

Step 2: Examine the second reaction. Cyclohexene (A) reacts with mCPBA (meta-chloroperoxybenzoic acid), which is a peracid. This reaction is an epoxidation, where the double bond in cyclohexene reacts with mCPBA to form an epoxide (compound H).

Step 3: Consider the third reaction. The epoxide (H) reacts with PhMgBr (phenylmagnesium bromide, a Grignard reagent) in ether. Grignard reagents attack the less substituted carbon of the epoxide, opening the ring and forming an alcohol intermediate after hydrolysis with dilute H3O+ (compound I).

Step 4: Analyze the final reaction. The alcohol (I) undergoes dehydration in the presence of H2SO4 under heat (Δ). This is an elimination reaction where H2SO4 acts as a catalyst, removing water to form an alkene (compound J).

Step 5: Summarize the sequence. The reactions involve elimination, epoxidation, nucleophilic attack by a Grignard reagent, and dehydration. Each step transforms the starting bromocyclohexane into progressively different functional groups, leading to the final alkene product.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile replaces a leaving group in a molecule. In the case of bromocyclohexane, the bromine atom acts as a leaving group, allowing nucleophiles to attack the carbon atom it was attached to. Understanding the mechanism (SN1 or SN2) is crucial for predicting the products of the reaction.

Electrophilic Addition

Electrophilic addition is a reaction where an electrophile reacts with a nucleophile, leading to the formation of a more saturated product. In the context of bromocyclohexane, if a double bond is present in the reactants, the bromine can add across the double bond, resulting in a new product. Recognizing the nature of the reactants helps in predicting the outcome of the reaction.

Reactivity of Alkyl Halides

Alkyl halides, such as bromocyclohexane, are reactive due to the polar C-X bond, where X is a halogen. The reactivity can vary based on the structure of the alkyl group (primary, secondary, or tertiary) and the type of reaction (substitution or elimination). Understanding these factors is essential for predicting how bromocyclohexane will react with different nucleophiles or electrophiles.

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Related Practice

Textbook Question

Using cyclohexanone as the starting material, describe how each of the following compounds can be synthesized:

Textbook Question

How could the following compounds be prepared, using cyclohexene as a starting material?

Textbook Question

Using the given starting material, any necessary inorganic reagents and catalysts, and any carbon-containing compounds with no more than three carbons, indicate how each of the following compounds can be prepared:

Textbook Question

Which of the reactions cannot be used for the synthesis of isobutyl alcohol?

Textbook Question

What reagents should be used to carry out the following syntheses?

Textbook Question

What reagents should be used to carry out the following syntheses?

Textbook Question

Starting with cyclohexene, how can the following compounds be prepared?

a. methoxycyclohexane

Textbook Question

Using 1,2-dimethylcyclohexene as your starting material, show how you would synthesize the following compounds. (Once you have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.) If a chiral product is shown, assume that it is part of a racemic mixture.

(f)

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For each synthesis, start with bromocyclohexane and predict the products. Assume that an excess of each reactant is added so that all possible reactions that can happen will happen.(c)

Key Concepts

Nucleophilic Substitution

Electrophilic Addition

Reactivity of Alkyl Halides

Watch next

For each synthesis, start with bromocyclohexane and predict the products. Assume that an excess of each reactant is added so that all possible reactions that can happen will happen.
(c)