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

10. Addition Reactions

Addition Reaction

Organic Chemistry

10. Addition Reactions

Addition Reaction

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2:11 minutes

Problem 50h

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.

(h)

Verified step by step guidance

Step 1: Begin with the starting material, 1,2-dimethylcyclohexene. The target compound has an alcohol (-OH) group attached to the carbon adjacent to the double bond. This suggests a hydration reaction.

Step 2: Use an acid-catalyzed hydration reaction to add water across the double bond. Employ a dilute acid such as H2SO4 in the presence of water. This reaction follows Markovnikov's rule, where the -OH group will attach to the more substituted carbon.

Step 3: Recognize that the product will be a racemic mixture if the reaction generates a chiral center. The stereochemistry of the product is not specified, so assume both enantiomers are formed.

Step 4: Verify the structure of the product. The -OH group should be attached to the carbon that is part of the original double bond and is more substituted, while the other carbon from the double bond will gain a hydrogen atom.

Step 5: Confirm that the resulting compound matches the target structure shown in the image, with the -OH group and a methyl group on the same carbon adjacent to the cyclohexane ring.

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Key Concepts

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

Electrophilic Addition Reactions

Electrophilic addition reactions are fundamental in organic chemistry, particularly for alkenes like 1,2-dimethylcyclohexene. In these reactions, an electrophile reacts with the double bond of the alkene, leading to the formation of a more stable carbocation intermediate. This process is crucial for synthesizing alcohols, halides, and other functional groups from alkenes.

Stereochemistry

Stereochemistry involves the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the context of synthesizing chiral compounds, understanding stereochemistry is essential, as it determines the configuration of the product. For example, when synthesizing 1,2-dimethylcyclohexanol, the stereochemical outcome can lead to different enantiomers, impacting the properties and reactivity of the compound.

Functional Group Interconversion

Functional group interconversion refers to the transformation of one functional group into another within a molecule. This concept is vital for organic synthesis, as it allows chemists to modify compounds to achieve desired properties. In the synthesis of compounds from 1,2-dimethylcyclohexene, converting the alkene to an alcohol (as seen in 1,2-dimethylcyclohexanol) exemplifies this principle, showcasing how different functional groups can be strategically introduced.

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Related Practice

Textbook Question

Synthesize the following molecules beginning with only organic molecules containing three carbons or fewer.

(g)

Textbook Question

Using any necessary inorganic reagents, show how you would convert acetylene and isobutyl bromide to

(a) meso-2,7-dimethyloctane-4,5-diol, (CH₃)₂CHCH₂CH(OH)CH(OH)CH₂CH(CH₃)₂.

Textbook Question

Predict the products formed when CH₃CH₂–C≡C:^–Na⁺ reacts with the following compounds.

a. ethyl bromide

b. tert-butyl bromide

c. formaldehyde

Textbook Question

Show how you would accomplish the following synthetic conversions.

c. 1-methylcyclopentanol → 2-chloro-1-methylcyclopentanol

Problem-Solving Hint: The opening of a halonium ion is driven by its electrophilic nature. The weak nucleophile attacks the carbon bearing more positive charge.

Textbook Question

Show what products you would expect from the following metathesis reactions, using the Schrock or Grubbs catalysts.

(a)

Textbook Question

Show what products you would expect from the following metathesis reactions, using the Schrock or Grubbs catalysts.

(c)

Textbook Question

Show how you might use olefin metathesis to assemble the following alkenes from smaller units:

(a)

(b)

Textbook Question

Starting with ethyne, describe how the following compounds can be synthesized: