Textbook Question
Predict the products formed when cyclohexanecarbaldehyde reacts with the following reagents.
(d) excess ethanol and acid
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Ch. 18 - Ketones and Aldehydes
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 18, Problem 54f
Predict the products formed when cyclohexanecarbaldehyde reacts with the following reagents.
(f) zinc amalgam and dilute hydrochloric acid
Verified step by step guidance1
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.
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Heck Reaction
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.
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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 synthesize octan-2-one from each compound. You may use any necessary reagents.
(b) oct-1-yne
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Textbook Question
Predict the products formed when cyclohexanecarbaldehyde reacts with the following reagents.
(e) propane-1,3-diol, H+
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Textbook Question
Predict the products formed when cyclohexanecarbaldehyde reacts with the following reagents.
(c) semicarbazide and weak acid
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Textbook Question
Show how you would synthesize octan-2-one from each compound. You may use any necessary reagents.
(c) 2,3-dimethylnon-2-ene
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Textbook Question
Show how you would synthesize octan-2-one from each compound. You may use any necessary reagents.
(a) heptanal
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