Carbonyls and isomers Flashcards

1
Q

What are the two main types of isomerism?

A

Structural isomerism and stereoisomerism

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2
Q

What are the three types of structural isomerism?

A

Chain isomerism, position isomerism, functional group isomerism

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3
Q

What are the two types of stereoisomerism?

A

Geometric isomerism and optical isomerism

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4
Q

Which organic molecules demonstrate optical isomerism?

A

Ones containing chiral carbons

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5
Q

How can chiral carbons be identified?

A

Carbon atoms with four different groups surrounding them

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6
Q

What are enantiomers?

A

Molecules with the same structural formula but exhibiting optical isomerism

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7
Q

How do enantiomers differ in terms of their mirror images?

A

They are non-superimposable upon their mirror images

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8
Q

How do enantiomers differ in terms of their effect on plane polarized light?

A

They rotate it in opposite directions

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9
Q

What is a racemic mixture?

A

A 50:50 mixture of two enantiomers

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10
Q

Explain the effect of a racemic mixture on plane polarized light

A

One enantiomer rotates the light clockwise and the other anti-clockwise, resulting in no net rotation.

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11
Q

Which homologous series are considered “carbonyls”?

A

Aldehydes and ketones

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12
Q

How can aldehydes and ketones be distinguished?

A

Fehling’s solution or Tollen’s reagent

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13
Q

How can aldehydes be formed?

A

Oxidation of a primary alcohol or reduction of a carboxylic acid

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14
Q

How can ketones be formed?

A

Oxidation of a secondary alcohol

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15
Q

Name the reagent and conditions for the reduction of carbonyl compounds

A

NaBH₄, aqueous

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16
Q

How is the reductant represented in equations?

A

[H]

17
Q

What is the name of the mechanism for the reduction of carbonyls?

A

Nucleophilic addition

18
Q

Under which conditions are hydroxynitriles formed?

A

Addition of KCN followed by dilute acid to a carbonyl

19
Q

Explain how nucleophilic additions of carbonyls with KCN can result in a racemic mixture

A

Carbonyl is planar, KCN can attack from above or below with equal probability, 50:50 chance of forming each enantiomer

20
Q

Which hazards are associated with using KCN?

A

It is highly toxic