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

19. Reactions of Aromatics: EAS and Beyond

EAS:Sequence Groups

Organic Chemistry

19. Reactions of Aromatics: EAS and Beyond

EAS:Sequence Groups

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3:18 minutes

Problem 54f

Textbook Question

Predict the products formed when cyclohexanecarbaldehyde reacts with the following reagents.
(f) zinc amalgam and dilute hydrochloric acid

Verified step by step guidance

Identify the functional group in cyclohexanecarbaldehyde. The molecule contains an aldehyde group (-CHO) attached to a cyclohexane ring.

Understand the role of zinc amalgam and dilute hydrochloric acid. This combination is used in the Clemmensen reduction, which reduces aldehydes and ketones to their corresponding alkanes.

In the Clemmensen reduction, the aldehyde group (-CHO) is reduced to a -CH3 group. This involves the removal of the oxygen atom from the aldehyde and the addition of two hydrogen atoms.

Write the reaction mechanism conceptually: The aldehyde group undergoes reduction in the presence of zinc amalgam and HCl, resulting in the formation of cyclohexane with a methyl group attached (cyclohexylmethane).

Verify the product structure: The aldehyde group is completely reduced, and no other functional groups are present in the molecule. The final product is cyclohexylmethane.

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Key Concepts

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

Wurtz Reaction

The Wurtz reaction involves the reduction of carbonyl compounds using zinc amalgam in the presence of an acid. In this context, cyclohexanecarbaldehyde is reduced to form cyclohexylmethanol. This reaction is significant in organic synthesis for converting aldehydes and ketones into alcohols.

Reduction Reactions

Reduction reactions in organic chemistry refer to the gain of electrons or decrease in oxidation state by a molecule. In the case of cyclohexanecarbaldehyde, the carbonyl group (C=O) is reduced to a hydroxyl group (C-OH), resulting in the formation of an alcohol. Understanding reduction mechanisms is crucial for predicting product formation.

Aldehyde Reactivity

Aldehydes are highly reactive due to the presence of the carbonyl group, which is polarized and susceptible to nucleophilic attack. In the reaction with zinc amalgam and dilute hydrochloric acid, the aldehyde undergoes reduction, highlighting its reactivity compared to other functional groups. Recognizing the behavior of aldehydes is essential for predicting reaction outcomes.

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Related Practice

Textbook Question

Show how you would use the Friedel–Crafts acylation, Clemmensen reduction, and/or Gatterman–Koch synthesis to prepare the following compounds:

Textbook Question

Show how you would use the Friedel–Crafts acylation, Clemmensen reduction, and/or Gatterman–Koch synthesis to prepare the following compounds:

Textbook Question

Show how you would use the Friedel–Crafts acylation, Clemmensen reduction, and/or Gatterman–Koch synthesis to prepare the following compounds:

e. 3-methyl-1-phenylbutane

Textbook Question

Show how you would use the Friedel–Crafts acylation, Clemmensen reduction, and/or Gatterman–Koch synthesis to prepare the following compounds:

f. 1-phenyl-2,2-dimethylpropane

Textbook Question

Predict the major products of the following reactions:

(a)

Textbook Question

Predict the major products of the following reactions.

Textbook Question

Show how you would use the Friedel–Crafts acylation, Clemmensen reduction, and/or Gatterman–Koch synthesis to prepare the following compounds:

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Predict the products formed when cyclohexanecarbaldehyde reacts with the following reagents. (f) zinc amalgam and dilute hydrochloric acid

Key Concepts

Wurtz Reaction

Reduction Reactions

Aldehyde Reactivity

Watch next

Predict the products formed when cyclohexanecarbaldehyde reacts with the following reagents.
(f) zinc amalgam and dilute hydrochloric acid