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Questions and Answers
What is the product of the Simmons-Smith reaction involving dichlorocarbene and an alkene?
Cyclopropane
What functional group is formed when acetylide anions add to aldehydes?
Secondary alcohols
What type of compound is produced when hydrogen cyanide adds to ketones?
Cyanohydrin
What type of reaction does the Wittig reaction represent?
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What are the products of the reduction of aldehydes using sodium borohydride and lithium aluminum hydride, respectively?
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What reagents are used to prepare Grignard reagents?
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How are organolithium reagents prepared?
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What reagents are used to prepare Gilman reagents?
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What type of compounds can Gilman reagents add to?
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What type of carbon atom does an organometallic compound add to in an epoxide?
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Study Notes
Simmons-Smith Reaction
- Involves the formation of cyclopropanes from alkenes using dichlorocarbene.
- Dichlorocarbene adds to the double bond of an alkene, resulting in a three-membered cyclic structure.
Acetylide Anions and Aldehydes
- Acetylide anions react with aldehydes to form alkynes.
- This addition results in the formation of a propargyl alcohol after hydrolysis.
Hydrogen Cyanide and Ketones
- Hydrogen cyanide adds to ketones to form cyanohydrins.
- This addition introduces a cyano group (–C≡N) to the carbonyl carbon.
Wittig Reaction
- Represents a method for converting carbonyl compounds into alkenes.
- Utilizes phosphonium ylides to form a unique alkenyl phosphonium intermediate, leading to alkene synthesis.
Reduction of Aldehydes
- Sodium borohydride reduces aldehydes to primary alcohols.
- Lithium aluminum hydride (LiAlH4) reduces aldehydes to primary alcohols more vigorously, often applicable in more challenging environments.
Grignard Reagents Preparation
- Prepared by reacting an alkyl or aryl halide with magnesium metal in dry ether.
- Grignard reagents are highly reactive organomagnesium compounds used in various carbon-carbon bond-forming reactions.
Organolithium Reagents Preparation
- Formed through the reaction of an alkyl or aryl halide with lithium metal.
- These reagents are strong nucleophiles and bases.
Gilman Reagents Preparation
- Prepared by reacting lithium diorganocuprate with alkyl or aryl halides.
- These compounds, also known as organocuprates, are used for coupling reactions.
Gilman Reagents Applications
- Can add to alkyl and aryl halides to form new carbon-carbon bonds.
- They are selective and can engage in various nucleophilic substitution reactions.
Organometallic Compounds and Epoxides
- Organometallic compounds add to the less hindered carbon atom of an epoxide.
- This reaction opens the epoxide ring and forms a new carbon-carbon bond.
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Description
Test your knowledge on common reagents and reactions covered in Chemistry 310, including the preparation of Grignard and Organolithium reagents. Understand the process of preparing Gilman reagents and their properties.
