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

22. Carboxylic Acid Derivatives: NAS

Nucleophilic Acyl Substitution

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Nucleophilic Acyl Substitution

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3:17 minutes

Problem 84a

Textbook Question

How can the following compounds be prepared from the given starting materials?
a.

Verified step by step guidance

Step 1: Analyze the starting material and the target compound. The starting material is a cyclopentanone derivative with a methoxy group attached to the carbonyl carbon. The target compound is a cyclopentane derivative with a tertiary alcohol group and two methyl groups attached to the same carbon.

Step 2: Recognize the transformation required. The reaction involves converting the carbonyl group into a tertiary alcohol and introducing two methyl groups. This suggests a nucleophilic addition reaction followed by reduction.

Step 3: Identify the reagent for methyl addition. Use a Grignard reagent, such as methyl magnesium bromide (CH₃MgBr), to add two methyl groups to the carbonyl carbon. This step forms a tertiary alcohol intermediate.

Step 4: Consider the reaction mechanism. The Grignard reagent attacks the electrophilic carbonyl carbon, breaking the double bond and forming a new C-C bond. The intermediate is then protonated to yield the tertiary alcohol.

Step 5: Ensure proper reaction conditions. Perform the reaction in an anhydrous ether solvent to stabilize the Grignard reagent and avoid side reactions. After the addition, use an acid workup (e.g., HCl or H₂O) to protonate the intermediate and complete the reaction.

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Key Concepts

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

Nucleophilic Acyl Substitution

Nucleophilic acyl substitution is a fundamental reaction in organic chemistry where a nucleophile attacks the carbonyl carbon of an acyl compound, leading to the replacement of a leaving group. This mechanism is crucial for transforming carboxylic acid derivatives into other functional groups, such as alcohols or amines, by introducing new substituents while maintaining the carbonyl structure.

Reactivity of Carbonyl Compounds

Carbonyl compounds, such as aldehydes and ketones, exhibit unique reactivity due to the polarized carbon-oxygen double bond. The carbon atom is electrophilic, making it susceptible to nucleophilic attack. Understanding the reactivity patterns of these compounds is essential for predicting the outcomes of organic reactions, including the formation of alcohols from acyl derivatives.

Stereochemistry in Organic Reactions

Stereochemistry refers to the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In reactions involving chiral centers, such as the one depicted, the stereochemical outcome can lead to different products. Recognizing the importance of stereochemistry is vital for understanding reaction mechanisms and predicting the configuration of the final products.

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Related Practice

Textbook Question

In each part, rank the compounds in order of increasing rate of nucleophilic attack at C=O by a strong nucleophile like methoxide.

(a)

Textbook Question

Show how you would convert 2-methylcyclopentanol to the following products. Any of these products may be used as the reactant in any subsequent part of this problem.

(g) 2-methylcyclopentyl acetate

(h) 1-bromo-1-methylcyclopentane

Textbook Question

Predict the product of the multistep synthesis reaction shown.

Textbook Question

Predict the product of the following reaction sequences.

(a)

Textbook Question

Show how you would synthesize each compound, starting with an ester containing no more than eight carbon atoms. Any other necessary reagents may be used.

(a) Ph₃C–OH

(b) (PhCH₂)₂CHOH

Textbook Question

Show how to synthesize the following amines from the indicated starting materials by acylation–reduction.

(a) N-butylpiperidine from piperidine

(b) N-benzylaniline from aniline

Textbook Question

Which compound forms an anhydride more rapidly?

Textbook Question

b. What is the product of the reaction of acetamide with HO⁻? The pK_a of NH₃ is 36; the pK_a of H₂O is 15.7.

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