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Questions and Answers
What is the role of a reducing agent in organic chemistry?
What is the role of a reducing agent in organic chemistry?
Which reagent is used to convert an alcohol to an alkyl halide in the conversion to an amine?
Which reagent is used to convert an alcohol to an alkyl halide in the conversion to an amine?
Which reaction converts a single-carbon molecule to a two-carbon molecule?
Which reaction converts a single-carbon molecule to a two-carbon molecule?
What is produced when an aldehyde is oxidized?
What is produced when an aldehyde is oxidized?
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Which reaction is used to reduce a carboxylic acid to an aldehyde?
Which reaction is used to reduce a carboxylic acid to an aldehyde?
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What is the result of dehydrohalogenation?
What is the result of dehydrohalogenation?
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What transformation occurs during the soda lime reaction?
What transformation occurs during the soda lime reaction?
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Which of the following conversions is not correctly paired with its reagents?
Which of the following conversions is not correctly paired with its reagents?
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Study Notes
Oxidation and Reduction Reactions
- Oxidation: Gain of oxygen or loss of hydrogen.
- Reducing Agent: Used to add hydrogen atoms to a molecule (example: Lithium Aluminum Hydride).
- Oxidizing Agent: Used to add oxygen atoms to a molecule (example: Potassium dichromate).
Conversion Reactions
- Alcohol to Aldehyde: Oxidize alcohol using an oxidizing agent.
- Aldehyde to Carboxylic Acid: Oxidize aldehyde using an oxidizing agent.
- Carboxylic Acid to Aldehyde: Reduce carboxylic acid using a reducing agent.
- Aldehyde to Alcohol: Reduce aldehyde using a reducing agent.
- Alkyl Halide to Alcohol: Add aqueous potassium hydroxide to an alkyl halide.
Increasing Carbon Atom Conversions
- Wurtz Reaction: Converts a single-carbon molecule to a two-carbon molecule (example: methane to ethane). Uses sodium and ether as reagents.
- Corey-House Reaction: Converts a two-carbon molecule to a three-carbon molecule (example: ethane to propane). Uses copper iodide, lithium, and methyl chloride as reagents.
Decreasing Carbon Atom Conversions
- Soda Lime Reaction: Converts a carboxylic acid to an alkane with one less carbon atom. Uses a mixture of sodium hydroxide and calcium hydroxide.
Bond Conversions
- Dehydrohalogenation: Converts a single bond to a double bond by removing hydrogen and halogen atoms. Uses alcoholic potassium hydroxide as a reagent.
- Conversion to Triple Bond: Converts a double bond to a triple bond by adding sodium amide (NaNH2).
- Reduction to Double Bond: Converts a triple bond to a double bond by reducing it with nickel and hydrogen.
- Reduction to Single Bond: Converts a double bond to a single bond by reducing it with nickel and hydrogen.
Important Conversions
- Alcohol to Amine: Use Lucas reagent (HCl and zinc chloride) to convert the alcohol to an alkyl halide, then add ammonia to the alkyl halide.
- Amine to Alcohol: Add nitrous acid (HNO2) to an amine.
- Amide to Amine: Use a Hofmann bromide reaction (bromine and potassium hydroxide) to convert an amide to an amine.
- Amine to Amide: Convert the amine to an alcohol via nitrous acid, oxidize the alcohol to an aldehyde and then to a carboxylic acid, react the carboxylic acid with ammonia to form an ammonium salt, and then heat the salt to form the amide.
- Nitro to Amine: Reduce the nitro group using a reducing agent like lithium aluminum hydride.
- Amine to Nitro: Convert the amine to an alcohol using nitrous acid, reduce the alcohol to an alkane using HI and red phosphorus, and then add fuming nitric acid to the alkane.
Example Conversion Problems
- Propanol to Ethyne: Oxidize propanol to propanoic acid, break the carboxylic acid using soda lime to form ethane, dehydrohalogenate ethane to ethene, and then add sodium amide to ethene to form ethyne.
- Propamine to Ethanol: Convert propamine to alcohol using nitrous acid, oxidize the alcohol to propanoic acid, break the carboxylic acid to ethane using soda lime, convert ethane to ethanol using potassium hydroxide, and then oxidize ethanol to ethanal.
Oxidation-Reduction Reactions
- Oxidation reactions involve gaining oxygen or losing hydrogen.
- Reducing agents add hydrogen atoms to a molecule, for example, lithium aluminum hydride.
- Oxidizing agents add oxygen atoms to a molecule, for example, potassium dichromate.
Alcohol Conversions
- Alcohols can be oxidized to aldehydes using oxidizing agents.
- Aldehydes can be further oxidized to carboxylic acids using oxidizing agents.
- Carboxylic acids can be reduced to aldehydes using reducing agents.
- Aldehydes can be reduced to alcohols using reducing agents.
- Alkyl halides can be converted to alcohols by adding aqueous potassium hydroxide.
Increasing Carbon Atom Conversions
- The Wurtz reaction combines two single-carbon molecules to form a two-carbon molecule. It utilizes sodium and ether.
- The Corey-House reaction increases the number of carbon atoms by one, for example, converting ethane to propane. Copper iodide, lithium, and methyl chloride are used as reagents.
Decreasing Carbon Atom Conversions
- The Soda Lime Reaction removes one carbon atom from a carboxylic acid, resulting in an alkane. This involves using a mixture of sodium hydroxide and calcium hydroxide.
Bond Conversions
- Dehydrohalogenation converts a single bond to a double bond. This involves removing a hydrogen and a halogen atom from a molecule using alcoholic potassium hydroxide.
- Sodium amide (NaNH2) converts a double bond to a triple bond.
- Triple bonds can be reduced to double bonds using nickel and hydrogen.
- Double bonds can be reduced to single bonds using nickel and hydrogen.
Important Conversions
- Alcohols can be converted to amines by first reacting with Lucas reagent to form an alkyl halide and then reacting with ammonia.
- Amines can be converted to alcohols using nitrous acid (HNO2).
- The Hofmann bromide reaction converts amides to amines using bromine and potassium hydroxide.
- Amines can be converted to amides by first transforming the amine to an alcohol using nitrous acid, then oxidizing the alcohol to an aldehyde and further to a carboxylic acid. The carboxylic acid is subsequently reacted with ammonia to form an ammonium salt, which is then heated to form the amide.
- Nitro groups can be reduced to amines using lithium aluminum hydride.
- Amines can be converted to nitro groups by first transforming the amine to an alcohol with nitrous acid, then reducing the alcohol to an alkane with HI and red phosphorus, and finally adding fuming nitric acid to the alkane.
Example Conversion Problems
- Propanol can be converted to ethyne through a series of steps: oxidation to propanoic acid, removal of one carbon using the soda lime reaction, dehydrohalogenation to ethene, and finally adding sodium amide to create ethyne.
- Propamine can be converted to ethanol by first converting it to an alcohol using nitrous acid, then oxidizing the alcohol to propanoic acid. Next, remove one carbon using the soda lime reaction, giving ethane. Convert ethane to ethanol using potassium hydroxide, and finally oxidize ethanol to ethanal.
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Description
This quiz explores key concepts of oxidation and reduction reactions, including the roles of reducing and oxidizing agents. It also covers conversion reactions among alcohols, aldehydes, and carboxylic acids, and introduces methods like Wurtz and Corey-House reactions to increase carbon atom count. Test your understanding of these fundamental chemical transformations.