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Questions and Answers
What is the primary difference between aldehydes and ketones in terms of their oxidation?
What is the primary difference between aldehydes and ketones in terms of their oxidation?
- Ketones are more easily oxidized than aldehydes.
- Aldehydes are more resistant to oxidation than ketones.
- Ketones are more easily oxidized to aldehydes than to carboxylic acids.
- Aldehydes are easily oxidized to carboxylic acids, while ketones are resistant to oxidation. (correct)
What is the purpose of Tollens' reagent in oxidation reactions?
What is the purpose of Tollens' reagent in oxidation reactions?
- To reduce the oxidation number of silver in the reaction.
- To catalyze the oxidation of aldehydes to carboxylic acids.
- To create a highly acidic environment for the reaction.
- To test for the presence of aldehydes in a molecule. (correct)
Which of the following oxidizing agents is used in alkaline conditions?
Which of the following oxidizing agents is used in alkaline conditions?
- Na2Cr2O7 (K2Cr2O7) in acid.
- KMnO4 in hot HNO3.
- CrO3 in strongly acidic conditions.
- Ag2O in aqueous ammonia solution. (correct)
What is the oxidation number of silver in Ag2O?
What is the oxidation number of silver in Ag2O?
What is the result of the reduction of silver in the Tollens' test?
What is the result of the reduction of silver in the Tollens' test?
What is the result of the reduction reaction when Tollens' reagent is added?
What is the result of the reduction reaction when Tollens' reagent is added?
What is the nature of the carbonyl group?
What is the nature of the carbonyl group?
What is the product of the nucleophilic addition of water to an aldehyde or ketone?
What is the product of the nucleophilic addition of water to an aldehyde or ketone?
What is the purpose of adding an acid to the O- ion?
What is the purpose of adding an acid to the O- ion?
What is the result of the reduction of the –CN group in a cyanohydrin?
What is the result of the reduction of the –CN group in a cyanohydrin?
What is the purpose of using a milder oxidizing agent in the partial oxidation of primary alcohols to prepare aldehydes?
What is the purpose of using a milder oxidizing agent in the partial oxidation of primary alcohols to prepare aldehydes?
What type of alkyne is required for the hydroboration-oxidation reaction to prepare an aldehyde?
What type of alkyne is required for the hydroboration-oxidation reaction to prepare an aldehyde?
Which of the following reactions is used to prepare ketones from secondary alcohols?
Which of the following reactions is used to prepare ketones from secondary alcohols?
What is the oxidizing agent used in the partial oxidation of primary alcohols to prepare aldehydes?
What is the oxidizing agent used in the partial oxidation of primary alcohols to prepare aldehydes?
What is the outcome of using internal alkynes in the hydroboration-oxidation reaction?
What is the outcome of using internal alkynes in the hydroboration-oxidation reaction?
What is the result of oxidation of aldehydes under acidic or alkaline conditions?
What is the result of oxidation of aldehydes under acidic or alkaline conditions?
What is the characteristic of ketones regarding oxidation?
What is the characteristic of ketones regarding oxidation?
What is the reagent used for oxidizing aldehydes under alkaline conditions?
What is the reagent used for oxidizing aldehydes under alkaline conditions?
What is the product formed when water is added to a carbonyl group?
What is the product formed when water is added to a carbonyl group?
What is the purpose of the Wolff-Kishner reaction?
What is the purpose of the Wolff-Kishner reaction?
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Study Notes
Grignard Reagents
- Grignard reagents are important in organic chemistry
- Hydrazine (N2H4) is a nucleophile that converts a carbonyl group (C=O) to -CH2 through reduction
- Wolff-Kishner reaction is a method of converting a carbonyl group to -CH2
Preparation of Aldehydes and Ketones
- Aldehydes can be prepared by:
- Partial oxidation of primary alcohols
- Ozonolysis of appropriate alkenes
- Partial reduction of an ester
- Hydroboration-oxidation of terminal alkynes
- Ketones can be prepared by:
- Oxidation of secondary alcohols
- Ozonolysis of appropriate alkenes
- Hydroboration-oxidation of internal alkynes
- Mercury(II)-catalyzed hydration of terminal and internal alkynes
Characteristics of Aldehydes and Ketones
- Aldehydes can be easily oxidized to carboxylic acids using various oxidizing agents
- Ketones are resistant to oxidation, but can react under harsh conditions to form carboxylic acids
- Aldehydes and ketones have a carbonyl group (C=O) which is polarized due to the difference in electronegativities between C and O
- This polarity makes the C atom susceptible to attack by electron-rich nucleophiles
Nucleophilic Addition
- Nucleophilic addition reactions involve the attack of a nucleophile on the partially positive C atom of the carbonyl group
- Nucleophiles can be fully negative ions (e.g. OH-, CN-, H-) or neutral but polar molecules (e.g. H2O, R-OH)
- Examples of nucleophilic addition reactions include:
- Hydration (addition of water) to form a 1,1-diol (geminal diol)
- Cyanohydrin formation (addition of HCN)
Transformations of Cyanohydrins
- Cyanohydrins can be transformed into useful compounds through:
- Reduction of the -CN group to -CH2NH2
- Hydrolysis of the -CN group to -COOH
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