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What is the primary function of sodium borohydride (NaBH4) in organic reactions?
What is the primary function of sodium borohydride (NaBH4) in organic reactions?
Lithium aluminum hydride (LiAlH4) can reduce carboxylates and esters.
Lithium aluminum hydride (LiAlH4) can reduce carboxylates and esters.
True
What are the two primary outcomes of the reduction of a carbonyl group?
What are the two primary outcomes of the reduction of a carbonyl group?
Alcohols (primary or secondary)
The process of converting an alcohol to a carbonyl compound is called ___ .
The process of converting an alcohol to a carbonyl compound is called ___ .
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Match the type of carbonyl compound with its reducing product:
Match the type of carbonyl compound with its reducing product:
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Which reducing agent is typically used when reducing ketones?
Which reducing agent is typically used when reducing ketones?
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Which reagent is often used for the reduction of primary alcohols?
Which reagent is often used for the reduction of primary alcohols?
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Nucleophilic addition occurs with carbonyl groups.
Nucleophilic addition occurs with carbonyl groups.
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In organic chemistry, oxidation is defined as the ___ hydrogen content.
In organic chemistry, oxidation is defined as the ___ hydrogen content.
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What does a nucleophile provide in a nucleophilic addition reaction to carbonyls?
What does a nucleophile provide in a nucleophilic addition reaction to carbonyls?
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Identify the product of the reduction of a carboxylic acid.
Identify the product of the reduction of a carboxylic acid.
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The carbonyl group is characterized by a polarized bond, with carbon being ___ and oxygen being ___.
The carbonyl group is characterized by a polarized bond, with carbon being ___ and oxygen being ___.
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Match the reducing agents with their applicable carbonyl types:
Match the reducing agents with their applicable carbonyl types:
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Increasing oxygen content in a molecule indicates oxidation.
Increasing oxygen content in a molecule indicates oxidation.
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Which of the following statements best describes a common characteristic of REDOX reactions?
Which of the following statements best describes a common characteristic of REDOX reactions?
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Which reagent is considered a milder oxidant for converting primary alcohols to aldehydes?
Which reagent is considered a milder oxidant for converting primary alcohols to aldehydes?
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Jones reagent can oxidize primary alcohols into carboxylic acids.
Jones reagent can oxidize primary alcohols into carboxylic acids.
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What is the primary reaction outcome when a secondary alcohol is oxidized with PCC?
What is the primary reaction outcome when a secondary alcohol is oxidized with PCC?
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The reaction of a primary alcohol with ___________________ will yield a carboxylic acid.
The reaction of a primary alcohol with ___________________ will yield a carboxylic acid.
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Match the following oxidizing agents with their respective products:
Match the following oxidizing agents with their respective products:
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Which statement is true regarding the oxidation of 3° alcohols?
Which statement is true regarding the oxidation of 3° alcohols?
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Organolithium reagents are best prepared in the presence of water.
Organolithium reagents are best prepared in the presence of water.
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Which organometallic reagent is commonly used for nucleophilic addition to carbonyl groups?
Which organometallic reagent is commonly used for nucleophilic addition to carbonyl groups?
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The bond character in organometallic compounds can range from primarily _____________ to covalent.
The bond character in organometallic compounds can range from primarily _____________ to covalent.
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Which of the following solvents is commonly used for preparing Grignard reagents?
Which of the following solvents is commonly used for preparing Grignard reagents?
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Alkyl lithium reagents can react with acidic protons.
Alkyl lithium reagents can react with acidic protons.
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What type of bond character increases the reactivity of organometallic reagents?
What type of bond character increases the reactivity of organometallic reagents?
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Nucleophilic substitution reactions can occur in organometallic compounds when there are ___________ protons.
Nucleophilic substitution reactions can occur in organometallic compounds when there are ___________ protons.
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Match the following compounds with their characteristics:
Match the following compounds with their characteristics:
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What type of alcohol is produced from the reaction of Grignard reagents with formaldehyde?
What type of alcohol is produced from the reaction of Grignard reagents with formaldehyde?
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Grignard reagents can react with esters to form primary alcohols only.
Grignard reagents can react with esters to form primary alcohols only.
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Identify a common reducing agent used for reducing ketones.
Identify a common reducing agent used for reducing ketones.
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Grignard reagents typically attack the less substituted carbon due to ________.
Grignard reagents typically attack the less substituted carbon due to ________.
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Match the following carbonyl compounds with their respective alcohol synthesis from Grignard reactions:
Match the following carbonyl compounds with their respective alcohol synthesis from Grignard reactions:
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Which reagent is more reactive: Grignard reagent or organolithium reagent?
Which reagent is more reactive: Grignard reagent or organolithium reagent?
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What is the result of a reaction between a ketone and a Grignard reagent?
What is the result of a reaction between a ketone and a Grignard reagent?
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When Grignard reagents react with carbonyls, they generate an ________ before protonation.
When Grignard reagents react with carbonyls, they generate an ________ before protonation.
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Which of the following is a common oxidizing agent?
Which of the following is a common oxidizing agent?
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Study Notes
Advanced Organic Chemistry - Chapter 1
- This chapter covers alcohols, carbonyls, and redox reactions, organometallic compounds, organolithium and magnesium compounds, reactions of organolithium/magnesium species, alcohols from Grignard reactions, and lithium dialkylcuprates.
The Carbonyl Functional Group
- The carbonyl group features a carbon atom double-bonded to an oxygen atom.
- Common carbonyl functional groups include aldehydes, ketones, carboxylic acids, and esters.
- The carbonyl group is planar and sp² hybridized.
- The carbonyl group has one sigma (σ) bond and one pi (π) bond.
- The carbonyl group is quite polarized (Cδ+, Oδ-).
- Resonance structures can be used describe the polarization of the bond
General Reactions of Carbonyls
- Nucleophilic addition to carbonyls.
- The addition product is tetrahedral.
- Oxidation of alcohols/reduction of carbonyls.
- Oxidation generally decreases hydrogen content and increases oxygen content.
- Reduction generally increases hydrogen content and decreases oxygen content.
Oxidation/Reduction Reactions
- Oxidation-reduction reactions are commonly termed "redox" reactions.
- Oxidation involves loss of electrons.
- Reduction involves gain of electrons.
- Organic chemists often use alternative definitions for redox reactions.
- Reduction: Increase hydrogen content (decrease oxygen)
- Oxidation: Decrease hydrogen content (increase oxygen)
- Oxidizing/reducing agents are usually inorganic compounds.
- Oxidizing agents get reduced during redox reactions.
- Reducing agents get oxidized during redox reactions.
Oxidation States of Carbon: Organics
- Oxidation state of carbons are calculated based on electronegativity differences with bonded atoms.
- Carbon bonded to more electronegative atom gets higher positive oxidation state.
- Carbon attached to less electronegative atom gets higher negative oxidation state.
Alcohol Synthesis: Carbonyl Reduction
- Carbonyls are reduced to alcohols using various hydrogen sources
- Aldehydes are reduced to primary alcohols.
- Ketones are reduced to secondary alcohols.
- Carboxylic acids and esters can also be reduced to alcohols.
- Common reducing agents include NaBH4 and LiAlH4
Reducing Agents: 1° and 2° Alcohols
- Sodium borohydride (NaBH4)
- Lithium aluminum hydride (LiAlH4)
- Hydrogen/transition metal catalyst (CuO/CuCr2O7)
- NaBH4 and LiAlH4 are hydride transfer agents.
- Hydride (H-) acts as a nucleophile.
- Carbonyls have varying degrees of ease of reduction.
Selection of a Reducing Agent
- The choice of reducing agent impacts the reaction products.
- LiAlH4 reduces carboxylates/esters to alcohols in preference over NaBH4.
NaBH4/LiAlH4 Reduction Examples
- Examples of NaBH4/LiAlH4 reductions of various carbonyl compounds
Oxidizing Agents in Organic Chemistry
- PCC (Pyridinium chlorochromate): mild oxidant, 1° alcohol → aldehyde.
- Jones Reagent (H₂CrO₄): Harsher oxidant, 1° alcohol → carboxylic acid.
General Oxidizing Agent Selection
- Oxidizing agents can determine oxidation products (e.g., PCC, Cr6+, KMnO4.)
- These agents are commonly used to oxidize alcohols to aldehydes or carboxylic acids.
- Oxidizing agents generally do not oxidize tertiary alcohols.
Oxidation of 1°, 2° Alcohols
- PCC, H₂CrO₄, and KMnO₄ are common oxidants used for different types of alcohols.
- PCC is effective for oxidizing primary alcohols to aldehydes.
- H₂CrO₄ and KMnO₄ are effective for oxidizing primary alcohols to carboxylic acids and for oxidizing secondary alcohols to ketones.
Oxidation Mechanisms: Chromate Esters
- Mechanisms of chromium-based oxidations are complex but often involve protonation and loss of water leading to chromate esters.
Organometallic Compounds
- Organometallic compounds contain carbon-metal bonds.
- Bonds range from ionic to primarily covalent
- Ionic C-M bonds include C-Na, C-K.
- Primarily covalent C-M bonds include C-Pb, C-Sn, C-Hg.
- Intermediate C-M bonds include compounds with C-Mg and C-Li.
- Reactivity increases with ionic character of C-M bond.
Organolithium Reagents
- Organolithium reagents are reactive carbanion-like species.
- They react slowly with ethers.
- Halide reactivity: RI > RBr > RCI
Grignard Reagents
- Grignard reagents are organometallic compounds.
- They are prepared by reacting alkyl halides with magnesium in an ether solvent.
- Halide reactivity of Grignard reagents is similar to organolithium reagents.
- Grignard reagents generally exist as complexes, often viewed as RMgX.
Organometallic Reactions: Notes
- Organometallic compounds can act as nucleophiles towards polarized carbonyl groups.
- They are very strong Lewis bases, reacting with acidic protons.
- Dry conditions are necessary for organometallic reactions to avoid reactions with water.
Grignard Reactions: Epoxides
- Grignard reagents open epoxides via nucleophilic attack to the less-substituted carbon due to steric hindrance.
Grignard Reactions w/ Carbonyls
- Grignard reagent react with carbonyls to form alcohols.
Grignard Reactions: Esters
- Grignard reagents react with esters to form tertiary alcohols.
- Esters react twice with Grignard.
Reactions of Organolithium Compounds
- Organolithium reagents react similarly to Grignard reagents.
- Same limitations to Grignard reagents apply to organolithium reagents.
Lithium Dialkylcuprates
- Lithium dialkylcuprates are used in carbon-carbon bond formation.
- They are quite versatile in forming carbon-carbon bonds.
Oxidation and Reduction (General Reactions)
- Various types of oxidizing and reducing agents are used in organic chemistry.
- These agents are commonly used in reactions for functional group transformations.
Oxidation and Reduction (Specific Reactions)
- Various types of oxidation and reduction reactions.
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Description
This quiz focuses on Chapter 1 of Advanced Organic Chemistry, covering key concepts such as alcohols, carbonyls, and redox reactions. It discusses the properties and reactions of organometallic compounds, including organolithium and magnesium reagents. Test your understanding of carbonyl functional groups and their general reactions.
