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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5:26 minutes

Problem 17c

Textbook Question

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

Verified step by step guidance

Step 1: Understand the reaction mechanism. Grignard reagents (R-MgX) are highly nucleophilic and react with acid chlorides or esters to form alcohols. In this case, the target alcohol is dicyclohexylphenylmethanol, which requires two equivalents of the Grignard reagent to add to the carbonyl group.

Step 2: Identify the starting material. To synthesize dicyclohexylphenylmethanol, you need an acid chloride or ester with a phenyl group attached to the carbonyl carbon. For example, phenylacetyl chloride or phenyl acetate can be used as the starting material.

Step 3: Select the Grignard reagent. The Grignard reagent should contain the cyclohexyl group (C₆H₁₁). For this synthesis, cyclohexylmagnesium bromide (C₆H₁₁-MgBr) is an appropriate choice.

Step 4: Perform the reaction. Add two equivalents of cyclohexylmagnesium bromide to the acid chloride or ester under anhydrous conditions. The first equivalent reacts with the carbonyl group to form a ketone intermediate, and the second equivalent reacts with the ketone to produce the tertiary alcohol.

Step 5: Workup and purification. After the reaction is complete, perform an acidic workup (e.g., using dilute HCl) to protonate the alkoxide intermediate and isolate the alcohol. Purify the product using techniques such as recrystallization or chromatography to obtain dicyclohexylphenylmethanol.

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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 that are highly reactive and used in organic synthesis. They are formed by reacting alkyl or aryl halides with magnesium metal in dry ether. Grignard reagents act as nucleophiles, attacking electrophilic centers such as carbonyl groups in aldehydes, ketones, esters, and acid chlorides, leading to the formation of alcohols after hydrolysis.

Acid Chlorides and Esters

Acid chlorides and esters are important functional groups in organic chemistry. Acid chlorides are derived from carboxylic acids by replacing the hydroxyl group with a chlorine atom, making them highly reactive. Esters, on the other hand, are formed from the reaction of carboxylic acids with alcohols. Both can react with Grignard reagents to form tertiary alcohols, with acid chlorides being more reactive than esters.

Synthesis of Alcohols

The synthesis of alcohols from Grignard reagents involves nucleophilic addition to carbonyl compounds. When a Grignard reagent reacts with an acid chloride or ester, it forms a tetrahedral intermediate, which upon hydrolysis yields the corresponding alcohol. This method is particularly useful for constructing complex alcohols, such as dicyclohexylphenylmethanol, by carefully selecting the appropriate Grignard reagent and carbonyl compound.

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Related Practice

Textbook Question

Often, compounds can be synthesized by more than one method. Show how this 3° alcohol can be made from the following:

Textbook Question

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

(c)

Textbook Question

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

(c)

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 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 this 1° alcohol can be made from the following:

(e) an alkene

(f) ethylene oxide

Textbook Question

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

(b)

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

Key Concepts

Grignard Reagents

Acid Chlorides and Esters

Synthesis of Alcohols

Watch next

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