Chapter 26 - Carbonyls and Carboxylic acids Flashcards

1
Q

What are the two carbonyl compounds and what are their functional groups?

A

Aldehyde -CHO
Ketone -CO

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2
Q

What does a primary alcohol form when oxidised?

A

Aldehyde

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3
Q

Under what conditions does a primary alcohol form an aldehyde?

A

Distillation
Acidified dichromate

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4
Q

What does a secondary alcohol form when oxidised?

A

Ketone

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5
Q

Under what conditions does a secondary alcohol form a ketone?

A

Reflux
Acidified dichromate

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6
Q

What do tertiary alcohols form when oxidised?

A

No reaction - tertiary alcohols cannot be oxidised

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7
Q

What colour change occurs when acidified dichromate is reduced by the alcohols?

A

Orange - to - green

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8
Q

What do aldehydes form when oxidised? And under what conditions?

A

Carboxylic acids
Reflux
Acidified dichromate

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9
Q

What does propanal form when oxidised?

A

Propanoic acid

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10
Q

What is the observation when aldehydes are oxidised?

A

Colour change from orange to green

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11
Q

Can ketones by oxidised? And what is the observation?

A

No
Colour remains orange

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12
Q

What is an addition reaction?

A

2 molecules joining together making a single product
Reaction has 100% atom economy

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13
Q

What is a nucleophile?

A

An electron pair donor

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14
Q

What is the nucleophile attracted to on the aldehyde?

A

The polar bond
Oxygen atoms are more electronegative and so there are partial charges

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15
Q

What are the two nucleophiles?

A

Hydride ion
Cyanide ion

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16
Q

What is the reducing agent for each of the nucleophiles?

A

NaBH4
HCN

17
Q

Can both aldehydes and ketones be reduced to alcohols?

A

Yes

18
Q

What do aldehydes form when reduced?

A

Primary alcohols

19
Q

What do ketones form when reduced?

A

Secondary alcohols

20
Q

What is the mechanism for nucleophilic addition with NaBH4 (aq)?

A

Dative covalent bond is formed
Undergoes heterolytic fission (C=O pi bond). Forming a negatively charged intermediate

21
Q

Draw out the mechanism for nucleophilic addition with HCN?

A
22
Q

What is used to make HCN in the least dangerous way?

A

Sodium cyanide
Sulfuric acid
Forming HCN in situ

23
Q

What is HCN useful for?

A

Extending carbon chain length.