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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5:50 minutes

Problem 7c

Textbook Question

Show how you would accomplish the following synthetic
conversions by adding an organolithium reagent to an acid.
(c) pentanoic acid → heptan-3-one

Verified step by step guidance

Step 1: Understand the reaction mechanism. Organolithium reagents are strong nucleophiles and bases. When added to a carboxylic acid, they first deprotonate the acid to form a carboxylate anion. This step is crucial for the subsequent reaction steps.

Step 2: For part (c), pentanoic acid → heptan-3-one: Add an organolithium reagent, such as propyl lithium (C3H7Li), to pentanoic acid. The carboxylic acid will be deprotonated to form pentanoate anion, and the organolithium reagent will act as a nucleophile in subsequent steps.

Step 3: After forming the carboxylate anion, react it with an electrophile, such as propyl bromide (C3H7Br), to introduce the propyl group. This step involves nucleophilic substitution, leading to the formation of an intermediate ketone.

Step 4: For part (d), phenylacetic acid → 3,3-dimethyl-1-phenylbutan-2-one: Add an organolithium reagent, such as tert-butyl lithium ((CH3)3CLi), to phenylacetic acid. The acid will be deprotonated to form phenylacetate anion, and the organolithium reagent will act as a nucleophile.

Step 5: React the phenylacetate anion with an appropriate electrophile, such as tert-butyl bromide ((CH3)3CBr), to introduce the tert-butyl group. This step involves nucleophilic substitution, leading to the formation of the desired ketone product.

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Key Concepts

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

Organolithium Reagents

Organolithium reagents are highly reactive compounds containing a carbon-lithium bond. They act as strong nucleophiles and are commonly used in organic synthesis to form carbon-carbon bonds. When added to carbonyl compounds or acids, they can facilitate the formation of new carbon chains, making them essential for various synthetic transformations.

Carboxylic Acid Reactivity

Carboxylic acids are organic compounds characterized by the presence of a carboxyl group (-COOH). They can undergo nucleophilic acyl substitution reactions, where nucleophiles, such as organolithium reagents, attack the carbonyl carbon. This reactivity is crucial for converting carboxylic acids into more complex molecules, such as ketones or alcohols.

Synthetic Pathways

Synthetic pathways refer to the series of chemical reactions that transform starting materials into desired products. Understanding these pathways is vital for planning synthetic routes in organic chemistry. In the context of the given conversions, identifying the correct sequence of reactions involving organolithium reagents and carboxylic acids is essential for achieving the target compounds.

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Related Practice

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

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

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

Predict the products of the following reactions:

(c)

(d)

Textbook Question

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

(d) phenylacetic acid → 3,3-dimethyl-1-phenylbutan-2-one

Textbook Question

Propose structures for intermediates and products (A) through (D).

Textbook Question

Devise a synthesis for each compound, starting with methylenecyclohexane and any other reagents you need.

f. 1-(phenylmethyl)cyclohexanol

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Show how you would accomplish the following syntheticconversions by adding an organolithium reagent to an acid.(c) pentanoic acid → heptan-3-one

Key Concepts

Organolithium Reagents

Carboxylic Acid Reactivity

Synthetic Pathways

Watch next

Show how you would accomplish the following synthetic
conversions by adding an organolithium reagent to an acid.
(c) pentanoic acid → heptan-3-one