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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5:41 minutes

Problem 36a,b

Textbook Question

Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).
(a)
(b)

Verified step by step guidance

Step 1: Recognize that the reaction involves a Grignard reagent (R-MgX) reacting with a carbonyl compound. Grignard reagents are nucleophiles that attack electrophilic carbonyl carbons, forming a new carbon-carbon bond.

Step 2: For reaction (a), identify the reactants: cyclohexylmagnesium bromide (Grignard reagent) and formaldehyde (H₂C=O). The Grignard reagent will attack the carbonyl carbon of formaldehyde, leading to the formation of a primary alcohol after hydrolysis.

Step 3: For reaction (b), identify the reactants: cyclopentylmagnesium chloride (Grignard reagent) and butanone (CH₃CH₂COCH₃). The Grignard reagent will attack the carbonyl carbon of butanone, leading to the formation of a tertiary alcohol after hydrolysis.

Step 4: After the nucleophilic attack, the intermediate alkoxide ion is formed. Hydrolysis (addition of water or acid workup) converts the alkoxide ion into the corresponding alcohol.

Step 5: Draw the organic products: (a) Cyclohexylmethanol (a primary alcohol) and (b) 1-cyclopentyl-2-methyl-2-butanol (a tertiary alcohol). Ensure the correct placement of the hydroxyl group and the new carbon-carbon bond in each product.

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Key Concepts

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

Hydrolysis

Hydrolysis is a chemical reaction involving the breaking of a bond in a molecule using water. In organic chemistry, it often refers to the conversion of esters, amides, or other functional groups into their corresponding acids and alcohols or amines. Understanding hydrolysis is crucial for predicting the products of reactions, especially when water is involved in the reaction mechanism.

Reaction Mechanisms

A reaction mechanism is a step-by-step description of how reactants transform into products during a chemical reaction. It includes the sequence of bond-breaking and bond-forming events, which helps in predicting the structure of the products. Familiarity with common mechanisms, such as nucleophilic substitution or elimination, is essential for accurately drawing the expected organic products.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Identifying functional groups in the reactants is vital for predicting the outcome of reactions, as they dictate how the molecule will behave during hydrolysis and what products will be formed. Common functional groups include alcohols, carboxylic acids, and amines.

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Related Practice

Textbook Question

Show how you would accomplish the following synthetic conversions by adding an organolithium reagent to an acid.

(a)

Textbook Question

Show how you would accomplish the following synthetic conversions by adding an organolithium reagent to an acid.

(b)

Textbook Question

Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).

(p)

Textbook Question

Predict the major products of the following reactions.

(g)

Textbook Question

Predict the products of the following reactions.

(d)

(e)

Textbook Question

Suggest the most appropriate method for each of the following laboratory syntheses. In each case, suggest both a chromium reagent and a chromium-free reagent.

(d) cyclopentanol → 1-ethylcyclopentanol (two steps)

(e) cyclopentylmethanol → 1-cyclopentylpropan-1-ol (two steps)

Textbook Question

Develop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols containing no more than four carbon atoms, and any common reagents and solvents.

(d)

Textbook Question

Show how you would synthesize the following compounds from any starting materials containing no more than six carbon atoms.

(b)

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