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

Grignard Reaction

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Grignard Reaction

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4:16 minutes

Problem 57e,f

Textbook Question

Show how this 1° alcohol can be made from the following:

(e) an alkene
(f) ethylene oxide

Verified step by step guidance

Step 1: To synthesize the given 1° alcohol from an alkene, identify the corresponding alkene structure. The alcohol shown has a hydroxyl group (-OH) attached to a primary carbon. The alkene precursor would be cyclopentyl ethene (cyclopentyl group attached to a double bond).

Step 2: Perform hydroboration-oxidation on the alkene. This reaction involves two steps: (a) Add BH₃ (borane) or a borane derivative to the alkene to form an organoborane intermediate. (b) Oxidize the organoborane intermediate using H₂O₂ (hydrogen peroxide) in a basic solution (NaOH). This results in anti-Markovnikov addition of water, forming the 1° alcohol.

Step 3: To synthesize the given 1° alcohol from ethylene oxide, identify the nucleophile that can attack the ethylene oxide ring. The nucleophile in this case would be cyclopentylmethyl anion (generated from cyclopentylmethyl bromide using a strong base like NaH).

Step 4: Perform a ring-opening reaction of ethylene oxide. The nucleophile attacks the less hindered carbon of the ethylene oxide ring, leading to the formation of a primary alcohol. This reaction is typically carried out in an aqueous or alcohol solvent.

Step 5: After the ring-opening reaction, ensure the product matches the structure of the desired 1° alcohol. Verify that the hydroxyl group is attached to the primary carbon and the cyclopentyl group is intact.

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Key Concepts

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

Alcohol Synthesis from Alkenes

The conversion of alkenes to alcohols typically involves hydration reactions. This can be achieved through acid-catalyzed hydration, where water adds across the double bond of the alkene, or through hydroboration-oxidation, which provides anti-Markovnikov addition. Understanding the mechanism and regioselectivity of these reactions is crucial for synthesizing the desired primary alcohol.

Ethylene Oxide as a Reactant

Ethylene oxide is a cyclic ether that can be used to produce alcohols through ring-opening reactions. When reacted with nucleophiles, such as alcohols or water, the strained ring opens, leading to the formation of a primary alcohol. This reaction is significant in organic synthesis, particularly for creating alcohols with specific stereochemistry.

Regioselectivity in Organic Reactions

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple possibilities exist. In the context of alcohol synthesis, understanding regioselectivity is essential to predict the major product formed from alkenes or cyclic ethers, ensuring the correct primary alcohol is synthesized based on the reaction conditions and reagents used.

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Related Practice

Textbook Question

Show how you would synthesize following tertiary alcohol by adding an appropriate Grignard reagent to a ketone.

c. 1-ethylcyclopentanol

Textbook Question

Show how you would add Grignard reagent to acid chloride or ester to synthesize the following alcohols.

c. dicyclohexylphenylmethanol

Textbook Question

Show how you would synthesize the following alcohol by adding Grignard reagents to ethylene oxide.

(c)

Textbook Question

Show how you would use Grignard syntheses to prepare the following alcohol from the indicated starting material and any other necessary reagents.

(d) 2-cyclohexylethanol from bromocyclohexane

Textbook Question

Show how you would synthesize the following primary alcohol by adding an appropriate Grignard reagent to formaldehyde.

(b)

Textbook Question

Show how you would synthesize following tertiary alcohol by adding an appropriate Grignard reagent to a ketone.

d. 2-cyclopentylpentan-2-ol

Textbook Question

Point out the flaws in the following incorrect Grignard syntheses.

(c)

(d)

Textbook Question

A variety of organometallics, which as strong nucleophiles can react with epoxides, are introduced in Chapter 16. Predict the product of these reactions. [Hint: Assume the carbon–metal bond in each is ionic, with the carbon possessing the negative charge.]

(b)

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Show how this 1° alcohol can be made from the following:(e) an alkene(f) ethylene oxide

Key Concepts

Alcohol Synthesis from Alkenes

Ethylene Oxide as a Reactant

Regioselectivity in Organic Reactions

Watch next

Show how this 1° alcohol can be made from the following:

(e) an alkene
(f) ethylene oxide