CH25 Isomerism Flashcards

1
Q

What property must a C have to display optical isomerism

A

4 different substituents attached to 1 C atom

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2
Q

Similarities between 2 optical isomers

A

Same atoms and bonds

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3
Q

Differences between 2 optical isomers

A

Differ in the way they rotate plane polarised light

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4
Q

Word used to describe optically active molecules

A

Chiral

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5
Q

What is a pair of isomers called

A

Enantiomers

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6
Q

What is a chiral centre

A

The carbon that has 4 different substituents attached to it

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7
Q

How is the chiral centre denoted

A

C*

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8
Q

How is light polarised

A

Passing it through a polaroid filter, so oscillations are only in one plane

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9
Q

What effect does the racemic mixture have on plane polarised light

A

None, as the rotation by each enantiomer cancels out to nothing

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10
Q

What effect does the + isomer have on plane polarised light

A

Rotates plane of polarisation by x degrees clockwise

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11
Q

What effect does the - isomer have on plane polarised light

A

Rotates plane of polarisation by x degrees anti-clockwise

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12
Q

What is the structure of a polarimeter

A

Light source –> polarising filter –> polarised light

passes through compartment with sample–> Detector determines angle of rotation of the plane of polarised light

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13
Q

What are polarimeters used for

A

To identify which enantiomer is present, the purity of the sample, the conc of the sample

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14
Q

First stage of synthesis of lactic acid

A

CH3CHO + HCN –> CH3CH(OH)CN

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15
Q

Why is CH3CH(OH)CN molecule chiral

A

Has H, CH3, OH and CN groups attached to it

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16
Q

Second stage of synthesis of lactic acid

A

CH3CH(OH)CN + HCl + 2H2O –> CH3CH(OH)COOH + NH4Cl

17
Q

How does this second stage affect chirality

A

Does not affect it - still racemic as chirality not affected by this stage

18
Q

Are racemic mixtures formed in nature - why

A

Not often - enzyme mechanisms 3D so only form 1 enantiomer

19
Q

Why is optical isomerism a problem for drug industry

A

Sometimes, only 1 enantiomer is effective due to 3D active site

20
Q

Options to resolve issue of 1 enantiomer being effective

A

Separate enantiomers - difficult + expensive
Sell racemate - wasteful as half inactive
Design alternate synthesis to only produce 1 enantiomer

21
Q

Example of optically active drugs

A

Ibuprofen

Thalidomide