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Questions and Answers

What type of reduction does NaBH4 primarily facilitate?

Reduction of amides

Reduction of esters

Reduction of aldehydes and ketones (correct)

Reduction of nitriles

What must be considered when using LiAlH4 in a reaction?

It should be used with water to enhance reactivity

It requires a heated environment to function properly

It can only be used in basic solutions

It must be used in anhydrous conditions due to its reactivity with water (correct)

What is the primary step involved in the reduction mechanism described?

Transfer of a hydride ion to the carbonyl carbon (correct)

Formation of a stable tetrahedral intermediate

Transfer of an electron to the carbonyl carbon

Oxygen atom substitution on the substrate

Which reagent is most unselective and powerful in reducing organic compounds?

LiAlH4 Signup and view all the answers

In the reaction of aldehydes and KOH, which products are primarily formed?

Alcohols and carboxylic acids Signup and view all the answers

What is the primary product formed when alkylbenzenes are oxidized?

Benzoic acid Signup and view all the answers

Which of the following reagents is considered the best for oxidizing alkylbenzenes?

Hot, alkaline KMnO4 Signup and view all the answers

What product does hot KMnO4 yield from oxidative cleavage of alkenes?

Carboxylic acids Signup and view all the answers

In oxidative cleavage of alkenes, what is formed if a terminal alkene is involved?

Carbon dioxide and water Signup and view all the answers

What happens to the ozonide formed during ozonolysis?

It is not usually isolated and is reduced to carbonyl. Signup and view all the answers

What is the initial product of ozonolysis before reduction?

Molozonide Signup and view all the answers

What is the result of the oxidative coupling of alkynes?

Formation of diynes Signup and view all the answers

Which of the following statements about oxidative coupling of phenols is true?

It plays a crucial role in biosynthesis of alkaloids. Signup and view all the answers

What is the primary role of NaBH4 in the reduction process shown?

To reduce carbonyl groups to alcohols Signup and view all the answers

Which reduction reaction is preferable when acid-labile groups are present?

Wolff-Kishner reduction Signup and view all the answers

What is one advantage of the Huang-Minlon modification of the Wolff-Kishner reduction?

It eliminates the need to isolate hydrazine Signup and view all the answers

Which method involves the use of H2S in aqueous alcoholic ammonia for selective nitro group reduction?

Nitro reduction Signup and view all the answers

In Meerwein-Ponndorff-Verley (MPV) reduction, what role does Al isopropoxide play?

It is the alkoxide used for reduction Signup and view all the answers

What is the next step in the Wolff-Kishner reduction after forming the hydrazone?

Heating with KOH Signup and view all the answers

What condition drives the equilibrium to favor the formation of alcohol in MPV reduction?

Removing acetone by distillation Signup and view all the answers

Which of the following is NOT a characteristic of MPV reduction?

It occurs under strongly acidic conditions Signup and view all the answers

What is the purpose of reductive amination?

Convert aldehydes and ketones to 1ry amines Signup and view all the answers

Which intermediate is formed during the reductive amination process?

imine Signup and view all the answers

What are benzene's products when treated with alkali metals in liquid ammonia and alcohol?

1,3-cyclohexadiene and 1,4-cyclohexadiene Signup and view all the answers

In Rosenmund reduction, which type of compound is converted to aldehydes?

Acid chlorides Signup and view all the answers

What is the role of BaSO4 in the Rosenmund reduction?

To poison the Pd catalyst and prevent over-reaction Signup and view all the answers

Which of the following is a side effect of using untreated Pd catalyst in Rosenmund reduction?

Further reaction to alcohols or alkane Signup and view all the answers

What happens to intermediates such as 1,3- and 1,4-cyclohexadiene when benzene is hydrogenated under pressure?

They rapidly hydrogenate to cyclohexane Signup and view all the answers

What is the final product when benzene is hydrogenated using H2 and a metal catalyst?

Cyclohexane Signup and view all the answers

What is the result of the loss of a proton and an electron?

Formation of a radical Signup and view all the answers

Which reagent is commonly used in Baeyer-Villiger oxidation?

Peracids Signup and view all the answers

In the migratory ability of substituents attached to a carbonyl, which group migrates most readily?

Cyclohexyl Signup and view all the answers

What is the general mechanism of epoxidation in the Prilezhaev Reaction?

Conversion of an alkene to an oxirane Signup and view all the answers

What characterizes the Cannizzaro Reaction?

Disproportionation of non-enolizable aldehydes Signup and view all the answers

What occurs during oxidative cleavage in Baeyer-Villiger oxidation?

Cleavage of C-C bond adjacent to carbonyl Signup and view all the answers

Which condition allows for the best stabilization of positive charges during migratory ability?

Resonance structures Signup and view all the answers

Which peracid can be used in epoxidation reactions?

Meta-chloro perbenzoic acid Signup and view all the answers

What does the term 'redox disproportionation' signify in the Cannizzaro Reaction?

Simultaneous oxidation and reduction of the same compound Signup and view all the answers

What type of molecular structure is formed at the end of the Baeyer-Villiger oxidation process?

An ester Signup and view all the answers

Study Notes

NaBH4 Reduction

NaBH4 primarily facilitates the reduction of aldehydes and ketones to alcohols.

LiAlH4 Reduction

When using LiAlH4, the reaction must be carried out in anhydrous conditions to prevent its decomposition by water.

Reduction Mechanism

The primary step involved in the reduction mechanism is the transfer of a hydride ion from the reducing agent to the carbonyl group.

Powerful Reducing Agents

LiAlH4 is the most unselective and powerful reducing agent in organic chemistry.

Aldehydes and KOH Reaction

The reaction of aldehydes with KOH primarily forms aldol condensation products.

Alkylbenzene Oxidation

The primary product formed when alkylbenzenes are oxidized is a carboxylic acid.

Best Reagent for Alkylbenzene Oxidation

KMnO4, especially hot KMnO4, is considered the best reagent for oxidizing alkylbenzenes.

Oxidative Cleavage of Alkenes

Hot KMnO4 yields carboxylic acids from the oxidative cleavage of alkenes.

Terminal Alkene Cleavage

In oxidative cleavage of alkenes, if a terminal alkene is involved, a carboxylic acid and CO2 are formed.

Ozonolysis Initial Product

The initial product of ozonolysis before reduction is an ozonide.

Ozonide Transformation

The ozonide formed during ozonolysis is then reduced to aldehydes or ketones.

Oxidative Coupling of Alkynes

The oxidative coupling of alkynes results in the formation of diynes.

Oxidative Coupling of Phenols

In oxidative coupling of phenols, the reaction typically involves the formation of dimeric products.

NaBH4 Role in Reduction

NaBH4 acts as a hydride donor, transferring a hydride ion to the carbonyl group during the reduction process.

Reduction with Acid-Labile Groups

When acid-labile groups are present, a milder reducing agent like NaBH4 is preferable over LiAlH4.

Wolff-Kishner Reduction Modification

The Huang-Minlon modification of the Wolff-Kishner reduction involves using a higher temperature and a stronger base, leading to a faster and more efficient reaction.

Nitro Group Reduction

The selective reduction of nitro groups can be achieved using H2S in aqueous alcoholic ammonia.

MPV Reduction Role of Aluminum Isopropoxide

In Meerwein-Ponndorff-Verley (MPV) reduction, Al isopropoxide acts as a catalyst and a hydride transfer agent.

Wolf-Kishner Reduction Next Step

After forming the hydrazone in the Wolff-Kishner reduction, the next step involves treating it with strong base and heat to generate the corresponding alkane.

MPV Reduction Equilibrium Shift

The equilibrium in MPV reduction favors alcohol formation when the reaction is driven towards product formation by removing the acetone formed as a byproduct.

MPV Reduction Characteristics

One characteristic of MPV reduction is that it is a non-catalytic reaction, meaning it does not require the use of a metal catalyst.

Purpose of Reductive Amination

Reductive amination is a useful method for synthesizing primary amines.

Reductive Amination Intermediate

An imine intermediate is formed during the reductive amination process.

Benzene Reaction with Alkali Metals

Benzene treated with alkali metals in liquid ammonia and alcohol generates a mixture of products, including cyclohexadiene and cyclohexene.

Rosenmund Reduction

Rosenmund reduction converts acid chlorides into aldehydes.

BaSO4 Role in Rosenmund Reduction

In Rosenmund reduction, BaSO4 is used as a catalyst poison to prevent the further reduction of the aldehyde to the corresponding alcohol.

Untreated Pd Catalyst Side Effect

Using untreated Pd catalyst in Rosenmund reduction can lead to the over-reduction of the aldehyde to the corresponding alcohol.

Benzene Hydrogenation Intermediates

Intermediates such as 1,3- and 1,4-cyclohexadiene are formed when benzene is hydrogenated under pressure.

Benzene Final Hydrogenation Product

The final product when benzene is hydrogenated using H2 and a metal catalyst is cyclohexane.

Loss of Proton and Electron

The loss of a proton and an electron usually leads to the formation of a radical.

Baeyer-Villiger Oxidation Reagent

Peracids, such as m-chloroperbenzoic acid (MCPBA), are commonly used reagents in Baeyer-Villiger oxidation.

Migration Ability in Baeyer-Villiger Oxidation

In Baeyer-Villiger oxidation, groups with electron-donating characteristics, like alkyl groups, migrate most readily.

Prilezhaev Reaction Mechanism

The general mechanism of epoxidation in the Prilezhaev Reaction involves the nucleophilic attack of the peracid oxygen on the alkene, followed by ring closure.

Cannizzaro Reaction

The Cannizzaro Reaction is a disproportionation reaction that involves the oxidation of one molecule of an aldehyde to a carboxylic acid and the reduction of another molecule of the same aldehyde to an alcohol, in the absence of an alpha hydrogen.

Oxidative Cleavage in Baeyer-Villiger Oxidation

Oxidative cleavage in Baeyer-Villiger oxidation refers to the breaking of the carbon-carbon bond adjacent to the carbonyl group.

Stabilization of Positive Charges

The best stabilization of positive charges during migratory ability in Baeyer-Villiger oxidation is achieved by groups that can effectively donate electrons to the developing carbocation.

Peracid in Epoxidation

Peracids like MCPBA, peracetic acid, and trifluoroperacetic acid are commonly used in epoxidation reactions.

Redox Disproportionation in Cannizzaro Reaction

The term 'redox disproportionation' in the Cannizzaro Reaction signifies the simultaneous oxidation and reduction of the same molecule.

End Product of Baeyer-Villiger Oxidation

At the end of Baeyer-Villiger oxidation, a lactone is formed.

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