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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3:50 minutes

Problem 21d

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

Verified step by step guidance

Step 1: Begin by identifying the target molecule, cyclopentyl propyl ketone. It consists of a cyclopentyl group attached to a propyl ketone functional group. The synthesis will require forming a carbon-carbon bond between the cyclopentyl group and the propyl ketone.

Step 2: Select an appropriate alkyl halide to introduce the cyclopentyl group. Cyclopentyl bromide (C₅H₉Br) is a suitable choice as it contains the cyclopentyl ring and can act as a nucleophile precursor.

Step 3: Choose a propyl halide to form the propyl ketone. Propyl bromide (C₃H₇Br) can be used as a starting material. Convert it into a propyl ketone by reacting it with a carbonyl compound, such as acetyl chloride (CH₃COCl), under Friedel-Crafts acylation conditions.

Step 4: Perform a coupling reaction to connect the cyclopentyl group to the propyl ketone. Use a Grignard reagent, such as cyclopentyl magnesium bromide (C₅H₉MgBr), prepared from cyclopentyl bromide and magnesium in dry ether. React the Grignard reagent with the propyl ketone to form the desired cyclopentyl propyl ketone.

Step 5: Purify the product using standard organic chemistry techniques, such as distillation or recrystallization, to isolate cyclopentyl propyl ketone in its pure form.

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Key Concepts

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

Alkyl Halides

Alkyl halides are organic compounds containing a carbon atom bonded to a halogen atom (such as chlorine, bromine, or iodine). They serve as versatile intermediates in organic synthesis, allowing for the formation of various functional groups through nucleophilic substitution or elimination reactions. Understanding their reactivity is crucial for designing synthetic pathways.

Grignard Reagents

Grignard reagents are organomagnesium compounds formed by reacting alkyl or aryl halides with magnesium metal. They are powerful nucleophiles that can react with carbonyl compounds to form alcohols. In the synthesis of cyclopentyl propyl ketone, Grignard reagents can be used to introduce the cyclopentyl group onto a suitable carbonyl precursor.

Carbonyl Chemistry

Carbonyl chemistry involves the study of compounds containing a carbonyl group (C=O), such as ketones and aldehydes. The reactivity of carbonyl compounds is central to many synthetic strategies, including nucleophilic addition and condensation reactions. In synthesizing cyclopentyl propyl ketone, understanding how to manipulate carbonyl compounds is essential for achieving the desired structure.

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Related Practice

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

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 accomplish the following synthetic

conversions by adding an organolithium reagent to an acid.

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).

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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

Key Concepts

Alkyl Halides

Grignard Reagents

Carbonyl Chemistry

Watch next

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