Aldehydes and Ketones and Optical isomerism Flashcards

1
Q

What is structural isomerism?

A

Same molecular formula but different structural formula

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2
Q

What is stereoisomerism?

A

Same structural formula but different arrangement of atoms in space

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3
Q

What are the three types of structural isomerism?

A

Chain, Positional and Functional

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4
Q

What are the two types of stereoisomerism?

A

Geometrical isomerism (E/Z)
Optical isomerism

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5
Q

What are optical isomers?

A

Non-super imposable mirror images

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6
Q

When can optical isomerism occur?

A

When a carbon atom bonds to 4 different groups

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7
Q

Definition of optical isomers

A

Rotate the plane of polarised light. One isomer will rotate it clockwise, the other isomer will rotate it anti-clockwise

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8
Q

What is an enantiomer?

A

Each optical isomer can be called enantiomer

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9
Q

What does enantiomerically pure mean?

A

If a sample contains only one optical isomer it is said to be enantiomerically pure

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10
Q

What does optically active mean?

A

An enantiomerically pure compound is optically active as it will rotate the plane of polarised light

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11
Q

What does racemic mixture mean?

A

A mixture which contains equal quantities of enantiomers

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12
Q

List the similar properties of optical isomers

A

same melting and boiling point
same solubility in a range of solvents
same Mr
same peaks in their NMR spectrum, IR spectrum and mass spectrum

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13
Q

What is the mechanism for the reduction of aldehydes and ketones?

A

Nucleophilic addition

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14
Q

What is the reagent of nucleophilic addition when forming an alcohol?

A

NaBH4

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15
Q

What is the condition of nucleophilic addition when forming an alcohol?

A

Acidic solvent

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16
Q

What is the mechanism when aldehydes and ketones form a hydroxyl nitrile?

A

Nucleophilic addition

17
Q

What is the reagent of nucleophilic addition when forming a hydroxyl nitrile?

A

KCN and HCl

18
Q

What is the conditon of nucleophilic addition when forming a hydroxyl nitrile?

A

acidic solvent

19
Q

Why can nucleophilic addition to aldehydes and ketones result in a racemic mixture to optical isomers?

A

The bonding about a C=O group in an aldehyde and ketone is planar
This means there is a 50:50 chance of the nucleophile attacking from one side of the molecule or the other
This results in equal proportions of each optical isomers forming and so a racemic mixture is formed