Chapter 16 - Organic synthesis Flashcards

1
Q

What 5 elements make up the quick-fit apparatus?

A
Pear-shaped flask
Receiver
Screw-tap adaptor
Condenser
Still head
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2
Q

Why is it advantageous to heat a material under reflux?

A

If you heat organic reactants, they’ll evaporate before they can react
It also avoids the use of a naked flame

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3
Q

What does it mean to heat a reactant under reflux?

A

The mixture is heated in a flask with a vertical Liebig condenser, which continuously boils, evaporates and condenses the vapours

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4
Q

What five pieces of kit are needed to heat under reflux?

A
Pear-shaped flask
Condenser
Rubber tubing
Stand with clamp
Heat source
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5
Q

How do you heat a mixture under reflux?

A

Set up your apparatus
Add the reaction mixture, along with some anti-bumping granules, to the flask
Apply a layer of grease to the joint on the condenser, to ensure the equipment can be dismantled at the end
Connect the rubber tubing to a water outlet

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6
Q

What do anti-bumping granules do?

A

They allow the contents to boil smoothly

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7
Q

Why is it important never to put a bung in the top of the condenser?

A

There would be too much pressure building up and the apparatus may explode

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8
Q

In what way should water enter the jacket?

A

Enter at the bottom and leave at the top

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9
Q

What is distillation used for?

A

Separating substances with different boiling points

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10
Q

What nine pieces of equipment are needed for distillation?

A
Pear-shaped flask
Condenser
Rubber tubing
Heat source
Stand and clamp
Screw-tap adaptor
receiver adaptor 
Still head
Thermometer
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11
Q

How do you heat a mixture under reflux?

A

Set up your apparatus and grease the joints of still head
Connect rubber tubing to a water outlet
Heat your mixture. The chemicals with the lowest boiling points will evaporate and be collected in the flask first
The vapour will move out of the flask and into the condenser, where it will condense and drip into the receiver flask

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12
Q

Why might you need to purify the mixture obtained from distillation or refluxing?

A

It might contain water

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13
Q

How do you purify a mixture?

A

1) Add some water to your mixture. The layer that increases in size is the aqueous layer (we don’t want this)
2) Pour the mixture into a separating funnel, ensuring the tap is closed
3) Place a bung in the top and invert to mix the contents
4) Allow the layers to settle
5) Place a flask under the tap, remove the stopper and run out the entire bottom layer into the flask
6) Run off the other layer into another flask
7) Discard the aqueous layer - your organic product is now purified

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14
Q

How would you remove acid impurities?

A

Add sodium carbonate and shake whilst in the separating funnel
The tap must be slowly opened, whilst holding the stoppered funnel upside down, to release any CO2 formed by the gas
Remove the sodium carbonate layer and repeat the normal method

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15
Q

What is anhydrous calcium chloride used for?

A

Drying hydrocarbons

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16
Q

What is anhydrous calcium sulfate used for?

A

General drying

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17
Q

What is anhydrous magnesium sulfate used for?

A

General drying

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18
Q

How do you dry an organic liquid?

A

Use a spatula to add some of the drying agent to the liquid and swirl to combine
Place a stopper in the flask to prevent the liquid evaporating and leave for ten minutes
If the solid has clumped together, there is still some water present, so add some more of the drying agent until the solid disperses
Decant the liquid from the solid into another flask

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19
Q

Why might you have to carry out redistillation?

A

Organic liquids have substances that are very close in boiling point

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20
Q

How do you carry out redistillation?

A

Carry out the distillation as normal but this time, only collect the product with the boiling point of the compound you are trying to make

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21
Q

How do you get a carboxylic acid?

A

Heat a primary acid under reflux with acidified potassium dichromate

22
Q

How do you get an aldehyde?

A

Distil a primary alcohol with acidified potassium dichromate

23
Q

How do you get a ketone?

A

Heat a secondary alcohol under reflux with acidified potassium dichromate

24
Q

What is produced when you react an alcohol with sodium halide and sulfuric acid?

A

A haloalkane

25
Q

What is produced when you react a haloalkane with sodium hydroxide under reflux?

A

An alcohol

26
Q

What is produced when you create an alcohol with concentrated sulfuric acid?

A

An alkene

27
Q

What is produced when you react an alkene with steam and a H3PO4 catalyst?

A

An alcohol

28
Q

What is produced when you react an alkene with hydrogen halide?

A

A haloalkane

29
Q

What is produced when you create an alkene with hydrogen and a nickel catalyst?

A

An alkane

30
Q

What is produced when you react an alkane with a halogen under UV light?

A

A haloalkane

31
Q

What does a synthetic route tell you?

A

How you get from one compound to another

32
Q

What must you include when asked how to make a chemical?

A

Any special procedures and the conditions needed

33
Q

What is a target molecule?

A

The compound that a chemist is trying to make by organic synthesis

34
Q

What are the three steps to describing organic synthesis?

A

Identify the functional groups in your starting and target molecules
Identify the intermediate linking these two
State the reagents and conditions needed for each step

35
Q

Which of the compounds we have studied have polar bonds?

A

Alcohols - C-OH
Haloalkanes - C-X
Aldehydes/ketones - C=O

36
Q

What reactions will alkanes typically undergo?

A

Radical substitution

37
Q

What reactions will alkenes typically undergo?

A

Electrophilic substitution

38
Q

What reactions will carboxylic acids typically undergo?

A

Esterification

39
Q

What reactions will aldehydes typically undergo?

A

Oxidation

40
Q

What reactions will haloalkanes typically undergo?

A

Nucleophilic substitution

41
Q

What reactions will alcohols typically undergo?

A

Nucleophilic substitution, dehydration/elimination

42
Q

Alcohol - ketone

A

Reflux secondary alcohol with H2SO4/K2Cr2O7

43
Q

Alcohol - carboxylic acid

A

Reflux primary alcohol with H2SO4/K2Cr2O7

44
Q

Alcohol - aldehyde

A

Distil primary alcohol with H2SO4/K2Cr2O7

45
Q

Alcohol - alkene

A

Conc. H2SO4

46
Q

Alkene - alcohol

A

Steam with H3PO4

47
Q

Alkene - alkane

A

H2 + Nickel

48
Q

Alkane - haloalkane

A

Halogen + UV

49
Q

Alkene - haloalkane

A

Hydrogen halide

50
Q

Alcohol - haloalkane

A

Sodium halide + H2SO4

51
Q

Haloalkane - alcohol

A

NaOH + reflux