6.1 - Isomerism and Carbonyl Compounds Flashcards

1
Q

What is optical isomerism?

A

A type of stereoisomerism where the molecule has a chiral carbon atom. This allows the molecule to be arranged differently in space and therefore causes two enantiomers to be produced.

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2
Q

How does an optical isomer change light?

A

Optical isomers rotate plane polarised light.

One enantiomer rotates light in a clockwise direction, the other in an anti-clockwise direction.

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3
Q

What is a racemic mixture?

A

A mixture that contains equal quantities of each enantiomer.

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4
Q

How does a racemic mixture affect light?

A

Racemic mixtures are optically inactive and therefore do not affect light passing through.

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5
Q

How does an aldehyde differ from a ketone?

A

An aldehyde has a carbonyl (C=O) group on the end of its carbon chain whereas a ketone has a carbonyl group in the middle of its carbon chain.

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6
Q

How does Tollens’ reagent distinguish between an aldehyde and a ketone?

A

Aldehyde - a silver mirror forms.

Ketone - No visible change.

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7
Q

How does Fehling’s solution distinguish between an aldehyde and a ketone?

A

Aldehyde - Turns brick-red from blue.

Ketone - No visible change.

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8
Q

What is an aldehyde reduced to?

A

A primary alcohol.

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9
Q

What is a ketone reduced to?

A

A secondary alcohol.

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10
Q

What chemical can be used to reduce an aldehyde or a ketone?

A

Sodium tetrahydridoborate(III) - NaBH4.

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11
Q

What is a hydroxynitrile?

A

A molecule that contains a hydroxyl group (OH) and a nitrile group (CN).

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12
Q

How are hydroxynitriles produced?

A

Reacting an aldehyde or ketone with acidified potassium cyanide.

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13
Q

Why can hydroxynitriles produce racemic mixtures.

A

Double bonds are planar and so nucleophiles can attack from either side of the double bond.

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14
Q

How is an ester produced?

A

Heating a carboxylic acid with an alcohol in the presence of a strong acid catalyst.

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15
Q

How is an ester named?

A

Name the alcohol side first (the single bond O) and then name the carboxylic acid side (double bond 0).

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16
Q

What are the two types of hydrolysis for an ester?

A

Acid hydrolysis and base hydrolysis.

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17
Q

What is produced during the acid hydrolysis of an ester?

A

A carboxylic acid and an alcohol. It is a reversible reaction.

18
Q

What is produced during the base hydrolysis of an ester?

A

A carboxylate ion and an alcohol. It is not a reversible reaction.

19
Q

How is a fat or oil made?

A

An esterification reaction between glycerol and fatty acids.

20
Q

What is the IUPAC name of glycerol?

A

Propane-1,2,3-triol.

21
Q

What are the two types of fats?

A

Saturated and unsaturated fats.

22
Q

Why do saturated fats have a higher boiling point than unsaturated fats?

A

Saturated fats can be packed closer together which increases the van der Waals forces between them.

23
Q

How can a fat/oil be hydrolysed?

A

Heat with sodium hydroxide.

24
Q

What does the hydrolysis of a fat produce?

A

Glycerol and a sodium salt.

25
Q

What is an acyl chloride?

A

A molecule with a COCl functional group.

26
Q

What is the general formula for an acyl chloride?

A

CnH2n-2OCl.

27
Q

How is an acyl chloride named?

A

Similar to a carboxylic acid but they end in -oyl chloride.

28
Q

What does an acyl chloride make when reacted with cold water?

A

A carboxylic acid and HCl.

29
Q

What is made when an acyl chloride is reacted with an alcohol?

A

An ester and HCl.

30
Q

What is made when an acyl chloride is reacted with ammonia?

A

An amide and HCl.

31
Q

What is made when an acyl chloride is reacted with a primary amine?

A

An N-substituted amide and HCl.

32
Q

What is an acid anhydride?

A

When two identical carboxylic acid molecules are joined together.

33
Q

How is an acid anhydride made?

A

Two identical carboxylic acids react to produce an acid anhydride and water.

34
Q

How is an acid anhydride named?

A

Take the name of the carboxylic acid used to produce the acid anhydride and take away the acid and add -anhydride.

35
Q

What is produced when an acid anhydride reacts with water?

A

Two carboxylic acids.

36
Q

What is produced when an acid anhydride reacts with an alcohol?

A

An ester and a carboxylic acid.

37
Q

What is produced when an acid anhydride reacts with ammonia?

A

An amide and a carboxylic acid.

38
Q

What is produced when an acid anhydride reacts with an amine?

A

An N-substituted amide and a carboxylic acid.

39
Q

How is aspirin produced?

A

By reacting salicylic acid with ethanoic anhydride or ethanoyl chloride.

40
Q

Why is ethanoic anhydride often used over ethanoyl chloride?

A

It is cheaper.

It is much safer as it doesn’t produce HCl fumes.