26.1 Carbonyl compounds Flashcards by Maya Hennig

What is the structural formula of the aldehyde group?

CHO

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What is the structural formula of the ketone group

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What is the suffix for aldehydes

______al

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what is the suffix for a ketone

_________one

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what is the suffix for a dialdehyde (2 aldehyde groups on a carbon chain)

______dial

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what is the suffix for a diketone (2 ketone groups on a carbon chain)

_______dione

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what is the suffix for a carbonyl group attached to a benzene ring?

_____carbaldehyde

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What is the prefix and suffix when both a hydroxy snd a carbonyl group are on a C chain

hydroxy_____al
hydroxy_______one

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What are the reagants and conditions for the oxidation of aldehydes to form carboxylic acids

-K2CR2O7, dilute H2SO4, reflux (oxidation)

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Do ketones undergo oxidation?

no, the C is making both C-C bonds and C=O have high enthalpy values so are unlikely to break

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Why is there a difference in reactions of alkenes and carbonyl functional groups

-C=C bond in alkenes is non-polar, reacts with electrophiles by electrophilic addition
-C=O bond in carbonyl compounds is polar so react with some nucleophiles in a nucleophilic addition reaction

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Why is a carbonyl compound a polar molecule?

-oxygen is more electronegative than carbon so the electron density in the double bond lies closer to the oxygen atom making the oxygen end slightly negative

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What is the C=O bond in carbonyl compounds made up of

a sigma bond
-a pi bond

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When reacting carbonyl compound with NaBH4 what is the role of NaBH4?

it is used as a reducing agent

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What are the reagents and conditions required for reducing an aldehyde

-compound is warmed with NaBH4 in aqueous solution
(NaBH4/H2O)

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What are aldehydes reduced to?

Primary alcohols

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What is the symbol used for a reducing agent?

[H]

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What are ketones reduced to?

Secondary alcohols

What are the properties of hydrogen cyanide (HCN)?

-colourless
-extremely toxic
-volatile as it is a small covalent compound
-boils slightly at room temperature

How do we reduce to toxicity of HCN (hydrogen cyanide)?

-it is mixed with NaCN to lower volatility and increase boiling point

Why is the reaction of hydrogen cyanide (HCN) with carbonyl compounds very useful?

as it increases the length of a carbon chain

What are the reagents used for the reaction of carbonyl compounds with HCN (hydrogen cyanide)

H2SO4 (sulfuric acid),NaCN (sodium cyanide)

What does the reaction of carbonyl compounds with HCN produce?

Hydroxynitriles

What happens during the reaction of carbonyl compounds with HCN?

The double bond breaks from the C=O to form a C-O which reacts with a hydrogen ion (H+) to produce an alcohol group (OH). The :-CN forms a bond with the C from a carbonyl group

What are the steps for the nucleophilic addition mechanism for reaction of carbonyl compounds with NaBH4/H20?

1. The lone pair of electrons from the hydride ion :H- is attracted and donated to the elctropostive carbon atom in the C=O bond 2. A dative covalent bond is formed between the hydride ion and the carbon of the C=O bond 3. The pi-bond in the C=O bond breaks by heterolytic fission forming a negatively charged intermediate 4. The oxygen atom of the intermediate donates a lone pair of electrons to a hydrogen atom in a water molecule. The intermediate has been pronated to form an alcohol

What is optical isomerism

non rotational, non-superimposable, mirror images, producing a racemic mixture (50/50)

What are the steps for the nucleophilic addition mechanism for reaction of carbonyl compounds with NaCN/H+?

1. The lone pair of electrons from the cyanide ion :-CN is attracted and donated to the the electropositive carbon atom and a dative covalent bond forms 2. the pi-bond in the C=O bond breaks by heterolytic fission forming a negatively charged intermediate 3. the intermediate is pronated by donating a lone pair of electrons to a hydrogen atom to form a product 4. the product is hydroxynitrile

What is the functional group of aldehydes and ketones?

Carbonyl functional group (C=O)

What is the prefix for an alcohol?

hydroxy____

What can aldehydes be oxidised to?

Carboxylic acids

What is the equation for the oxidation of butanal?

What are the products of the oxidation of aldehydes?

Carboxylic acids

Why is a carbonyl group polar?

Oxygen is more δ− than carbon, so the electron density in the double bond lies closer to he oxygen atom, makes the carbon end of the bond slightly positive (δ+) and oxygen slightly negative (δ−)

Why does the C=O bond in aldehydes and ketones react with nucleophiles?

The nucleophile is attracted to and attacks the slight positive carbon atom resulting in addition across the C=O

What is the equation for the reduction of butanal?

What is the equation for the reduction of propanone?

What is the name of the mechanism for reducing a carbonyl compound (aldehyde, ketone)?

Nucleophilic addition

What is the mechanism for reaction of ketone with NaBH4?

What is the nucleophile for reaction of carbonyl compound with NaBH4?

:H- (hydride ion)

What is the equation for the reaction of propanol with hydrogen cyanide?

What type of reaction is the reaction of carbonyl compounds with HCN?

Addition

What is the name of the mechanism for reaction of carbonyl compounds with NaCN/H+?

Nucleophilic addition

In the nucleophilic addition of carbonyl compounds with NaCN/H+ what are the two options for protonation?

Acid - H+ Water - H2O

How does the nucleophilic addition with NaCN involve heterolytic fission?

-Oxygen atom receives both electrons -Breaking of a covalent bond