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

13. Alcohols and Carbonyl Compounds

Organometallic Cumulative Practice

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Organometallic Cumulative Practice

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3:01 minutes

Problem 50a

Textbook Question

Using bromocyclohexane as a starting material, how could you synthesize the following compounds?
a.

Verified step by step guidance

Step 1: Analyze the starting material, bromocyclohexane. It contains a bromine atom attached to a cyclohexane ring, making it a good candidate for substitution or elimination reactions.

Step 2: To synthesize the target compound, methylcyclohexene, an elimination reaction is required to remove the bromine atom and form a double bond. This can be achieved using a strong base such as potassium tert-butoxide (KOtBu) or sodium ethoxide (NaOEt).

Step 3: Choose the appropriate conditions for elimination. Use a strong base and heat to favor the E2 elimination mechanism, which will result in the formation of the double bond. The base will abstract a proton from a β-carbon, and the bromine will leave as a leaving group.

Step 4: Consider regioselectivity. The double bond will form preferentially at the more substituted position due to Zaitsev's rule, resulting in the methylcyclohexene product.

Step 5: After the reaction, purify the product using techniques such as distillation or chromatography to isolate the desired methylcyclohexene compound.

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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 this mechanism is crucial for predicting the products formed during the synthesis of various compounds.

Stereochemistry

Stereochemistry refers to the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the synthesis of compounds from bromocyclohexane, the stereochemical configuration of the starting material can influence the outcome of the reaction, including the formation of stereoisomers. Recognizing the importance of stereochemistry is essential for accurately predicting the structure of the synthesized compounds.

Reagents and Reaction Conditions

The choice of reagents and reaction conditions is critical in organic synthesis, as they determine the pathway and efficiency of the reaction. For synthesizing compounds from bromocyclohexane, specific nucleophiles and solvents may be required to facilitate the desired transformations. Understanding how different reagents interact and the conditions that favor certain reactions is vital for successful synthesis.

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Textbook Question

What are the products of the following reactions?

Textbook Question

What are the products of the following reactions? Show all stereoisomers that are formed.

Textbook Question

What product is formed when 3-methyl-2-cyclohexenone reacts with each of the following reagents?

a. CH₃MgBr followed by H₃O⁺

b. (CH₃CH₂)₂CuLi followed by H₃O⁺

Textbook Question

The Reformatsky reaction is an addition reaction in which an organozinc reagent is used instead of a Grignard reagent to add to the carbonyl group of an aldehyde or a ketone. Because the organozinc reagent is less reactive than a Grignard reagent, a nucleophilic addition to the ester group does not occur. The organozinc reagent is prepared by treating an α-bromo ester with zinc.

Describe how each of the following compounds can be prepared, using a Reformatsky reaction:

Textbook Question

What alcohols are formed from the reaction of ethylene oxide with the following organocuprates followed by the addition of acid?

b. (CH₃CH=CH)₂CuLi

Textbook Question

Show how you would synthesize the following compound from alkyl halides, vinyl halides, and aryl halides containing no more than six carbon atoms.

(d) cyclopentyl propyl ketone

Textbook Question

Show how you would accomplish the following synthetic

conversions by adding an organolithium reagent to an acid.

Textbook Question

Predict the products of the following reactions:

(c)

(d)

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Using bromocyclohexane as a starting material, how could you synthesize the following compounds?a.

Key Concepts

Nucleophilic Substitution

Stereochemistry

Reagents and Reaction Conditions

Watch next

Using bromocyclohexane as a starting material, how could you synthesize the following compounds?
a.