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

Nucleophilic Addition

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Nucleophilic Addition

Previous problemNext problem

6:36 minutes

Problem 16b

Textbook Question

Show how you would accomplish the following syntheses.
b. cyclopentanecarbaldehyde → 2-cyclopentyl-2-hydroxyacetic acid

Verified step by step guidance

Step 1: Begin by identifying the functional groups in the starting material (cyclopentanecarbaldehyde) and the target molecule (2-cyclopentyl-2-hydroxyacetic acid). Cyclopentanecarbaldehyde contains an aldehyde group (-CHO), while the target molecule contains a hydroxyl group (-OH) and a carboxylic acid group (-COOH) attached to the same carbon.

Step 2: Plan the transformation of the aldehyde group into a carboxylic acid group. This can be achieved through oxidation. Use an oxidizing agent such as potassium permanganate (KMnO₄) or chromium-based reagents like Jones reagent (CrO₃/H₂SO₄) to convert the aldehyde (-CHO) to a carboxylic acid (-COOH).

Step 3: Introduce the hydroxyl group (-OH) at the alpha-carbon of the carboxylic acid. This can be accomplished through an aldol reaction or a hydroxylation step. For example, you can use a base like NaOH to generate an enolate intermediate, followed by reaction with an appropriate electrophile to add the hydroxyl group.

Step 4: Ensure stereochemistry is correct for the hydroxyl group addition. If stereoselectivity is required, consider using reagents or conditions that favor the desired stereochemical outcome, such as chiral catalysts or specific reaction temperatures.

Step 5: Purify the product (2-cyclopentyl-2-hydroxyacetic acid) using techniques like recrystallization or chromatography to ensure the final compound is free of impurities and matches the desired structure.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In this synthesis, understanding the aldehyde functional group in cyclopentanecarbaldehyde and the carboxylic acid group in 2-cyclopentyl-2-hydroxyacetic acid is crucial, as these groups dictate the reactivity and transformation pathways during the synthesis.

Nucleophilic Addition Reactions

Nucleophilic addition reactions involve the attack of a nucleophile on an electrophilic carbon atom, typically found in carbonyl compounds like aldehydes. In this synthesis, the nucleophilic attack of a hydroxyl group on the carbonyl carbon of cyclopentanecarbaldehyde is a key step in forming the desired hydroxy acid product, highlighting the importance of understanding reaction mechanisms.

Stereochemistry

Stereochemistry is the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the synthesis of 2-cyclopentyl-2-hydroxyacetic acid, recognizing the stereochemical implications of the hydroxyl group addition is essential, as it can lead to different isomers that may have distinct properties and reactivities.

Watch next

Master Nucleophilic Addition with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

Within each set of structures, indicate which will react fastest, and which slowest, toward nucleophilic addition in basic conditions.

(a)

379

views

Textbook Question

Show how you would synthesize each compound, beginning with acetylene and any necessary additional reagents

(c)

(d)

475

views

Textbook Question

Within each set of structures, indicate which will react fastest, and which slowest, toward nucleophilic addition in basic conditions.

(c)

316

views

Textbook Question

Within each set of structures, indicate which will react fastest, and which slowest, toward nucleophilic addition in basic conditions.

(b)

436

views

Textbook Question

Propose a mechanism for the following reactions:

469

views

Textbook Question

Predict the product of the following aldehyde and ketone addition reactions.

(b)

465

views

Textbook Question

Classify the following nucleophiles as strong, weak, or intermediate. Would you expect each to add to a carbonyl directly or wait for a carbocation to form?

(a)

537

views

Textbook Question

Classify the following nucleophiles as strong, weak, or intermediate. Would you expect each to add to a carbonyl directly or wait for a carbocation to form?

(d)

530

views

Show more practices