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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5:13 minutes

Problem 19a

Textbook Question

Show how you would synthesize the following alcohol by adding Grignard reagents to ethylene oxide.
(a) 2-phenylethanol

Verified step by step guidance

Step 1: Understand the reaction mechanism. Grignard reagents are organomagnesium compounds (R-MgX) that act as nucleophiles. They attack electrophilic centers, such as the carbon in ethylene oxide, to form new carbon-carbon bonds.

Step 2: Identify the Grignard reagent needed. To synthesize 2-phenylethanol, the Grignard reagent should contain a phenyl group (C₆H₅). Therefore, the Grignard reagent to use is phenylmagnesium bromide (C₆H₅-MgBr).

Step 3: React the Grignard reagent with ethylene oxide. The phenylmagnesium bromide will attack the electrophilic carbon in ethylene oxide, opening the epoxide ring and forming a new bond between the phenyl group and one of the carbons in the ethylene oxide.

Step 4: Perform hydrolysis. After the Grignard reagent reacts with ethylene oxide, the intermediate product is treated with water or dilute acid to protonate the oxygen atom, resulting in the formation of 2-phenylethanol.

Step 5: Verify the product structure. The final product should have a phenyl group attached to a two-carbon chain ending in an alcohol group (-OH), which matches the structure of 2-phenylethanol.

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Key Concepts

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

Grignard Reagents

Grignard reagents are organomagnesium compounds represented as R-MgX, where R is an organic group and X is a halogen. They are highly reactive and serve as nucleophiles in organic synthesis, allowing for the formation of carbon-carbon bonds. When reacted with electrophiles, such as carbonyl compounds or epoxides, they can lead to the formation of alcohols, making them essential in synthetic organic chemistry.

Ethylene Oxide

Ethylene oxide is a three-membered cyclic ether that is highly reactive due to its strained ring structure. It can undergo nucleophilic attack, making it a useful substrate for Grignard reagents. When a Grignard reagent attacks ethylene oxide, it opens the epoxide ring, leading to the formation of an alcohol after subsequent protonation, which is crucial for synthesizing specific alcohols like 2-phenylethanol.

Synthesis of Alcohols

The synthesis of alcohols often involves the addition of nucleophiles to electrophiles. In this case, the nucleophilic Grignard reagent adds to the electrophilic carbon of the ethylene oxide, resulting in the formation of a new carbon-carbon bond. This process is fundamental in organic chemistry, as it allows for the construction of complex molecules and the introduction of functional groups, such as hydroxyl groups in alcohols.

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Related Practice

Textbook Question

Show how to make these deuterium-labeled compounds, using CD₃MgBr and D₂O as your sources of deuterium, and any non-deuterated starting materials you wish.

b. CH₃C(OH)(CD₃)₂

Textbook Question

Show how to make these deuterium-labeled compounds, using CD₃MgBr and D₂O as your sources of deuterium, and any non-deuterated starting materials you wish.

a. CH₃CH(OD)CD₃

Textbook Question

Show how you would synthesize the following:

a. 2-phenylethanol by the addition of formaldehyde to a suitable Grignard reagent

Textbook Question

Acetylide ions also add to ethylene oxide much like Grignard and organolithium reagents. Predict the products obtained by adding the following acetylide ions to ethylene oxide, followed by a dilute acid workup.

(a) HC≡C:^–

(b) CH₃CH₂–C≡C:^–

Textbook Question

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

a. Ph₃C–OH

Textbook Question

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

b. Ph₃COH

Textbook Question

Show two ways you could synthesize each of the following secondary alcohol by adding an appropriate Grignard reagent to an aldehyde.

(a)

Textbook Question

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

(a)

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Show how you would synthesize the following alcohol by adding Grignard reagents to ethylene oxide. (a) 2-phenylethanol

Key Concepts

Grignard Reagents

Ethylene Oxide

Synthesis of Alcohols

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Show how you would synthesize the following alcohol by adding Grignard reagents to ethylene oxide.
(a) 2-phenylethanol