Chapter 25 (Nomenclature) Flashcards

1
Q

Define Structural Isomerism

A

Same molecular formula but different structure (atoms arranges differently along molecule).

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2
Q

What are the three types of structural isomerism?

A

Chain, Positional, Functional Group

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3
Q

Define Functional Group Isomerism

A

Compounds with the same molecula formula but atoms arranged to give different functional groups so in different homologous series.

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4
Q

Define Chain Isomerism

A

Alkyl groups move along carbon chain.

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5
Q

Define Positional Isomerism

A

Functional group moves along the chain so different number for functional group

e.g. in primary and secondary alcohols propane-1-ol propan-2-ol

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6
Q

Define Stereoisomerism

A

Compounds have the same molecular and structural formula but atoms have a different arrangement in space.

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7
Q

What are the two types of stereoisomerism?

A

Geometric and Optical

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8
Q

Why are geometric isomers created?

A

Restricted rotation about a C=C bond and two components around the bond are different.

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9
Q

Why do E-Z isomers have different properties?

A

E isomers can pack more tightly together so have higher melting points.

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10
Q

Define a chiral carbon?

A

4 different groups attached to a carbon so it is asymmetrical.

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11
Q

Define Optical Isomerism

A

When chiral carbons which have the same molecular and structural formula have non-superimposable mirror images.

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12
Q

What shape does a chiral carbon have?

A

Tetrahedral (109.5º)

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13
Q

What are 3D non-superimposable mirror images called?

A

Enantiomers

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14
Q

What are the two differences between enantiomers?

A
  • They interact differently with plane polarised light by rotating it in opposite directions but by the same amount. This is know as being optically active.
  • They react differently with other asymmetrical molecules such as enzymes and proteins.
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15
Q

Define Optically Active

A

When enantiomers rotate plane polarised light in the opposite direction by the same amount.

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16
Q

Define Racemate/Racemic Mixture

A

When there is an equal mix of both enantiomers so they are optically inactive so they cancel each other out.

17
Q

How are racemates formed?

A

When there is a trigonal planar group (e.g. carbonyl) so the molecule is equally likely to be attacked by a species from both sides.

18
Q

Why are most drugs marketed as racemates?

A

It is very difficult and expensive to separate enantiomers.

19
Q

How can a resolution (separation) of enantiomers be achieved?

A
  • Reaction with a chiral reactant, creating products with different physical properties e.g. solubility.
  • Chromatography
20
Q

What is the suffix for esters?

A

-oate

21
Q

What is the suffix for acyl chloride?

A

-oyl chloride

22
Q

What is the suffix for acid anhydride?

A

-oic anhydride

23
Q

What is the functional group of esters?

A

COO

24
Q

What is the functional group of acyl chloride?

A

COCl

25
Q

What is the functional group of acid anhydride?

A

CO-O-CO