Chapter 28 Organic Synthesis Flashcards

1
Q

What type of mechanism is involved in the reaction between haloalkanes and cyanide ions?

A

Nucleophilic substitution

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2
Q

What type of reaction is involved in the reaction between carbonyl compounds and cyanide ions?

A

Nucleophilic addition

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3
Q

How do you form a carboxylic acid from nitrile?

A

Acid hydrolysis

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4
Q

What type of catalyst is used for a Friedel-Crafts reaction?

A

A halogen carrier (e.g. AlCl3)

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5
Q

How could you use a Friedel-Crafts mechanism to add a methyl group to a benzene ring?

A

Use a halogenoalkane and AlCl3 to create an electrophile that can attack benzene.

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6
Q

When purifying by recrystallisation, why is the minimum volume of hot solvent used?

A

So that a saturated solution is created, so that as many crystals will fall out of solution as possible when it is cooled.

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7
Q

Why is the solution filtered hot when purifying by recrystallisation?

A

To remove insoluble impurities and ensure that the crystals do not form in the filter paper.

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8
Q

Why is the solution cooled in an ice bath when purifying by recrystallisation?

A

To ensure that as many as possible fall out of solution - yield is higher

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9
Q

Why are the crystals washed with cold water when purifying but recrystallisation?

A

To remove soluble impurities

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10
Q

How could you separate the crystals from the reaction mixture when purifying by recrystallisation?

A

Filter under reduced pressure using a Büchner funnel

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11
Q

Why might percentage yield be below 100%? (Practical reasons)

A

Product is lost during filtration, drying and weighing spills, not all transferred from one piece of apparatus to the other.

Product is left dissolved in the solution - some does not crystallise. Some left on filter paper. Sample still wet.

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12
Q

Describe how quick fit apparatus is connected.

A

Grease the joints using some petroleum jelly on the inside of the joints before connecting the pieces together.

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13
Q

In a distillation set up, why is it necessary to have a continuous water flow around the condenser?

A

So that the water remains cool in order for the mixture to be distilled.

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14
Q

Describe a method that can be used to separated immiscible liquids.

A

. pour the mixture into a separating funnel and some distilled water

. Add the stopper and invert the flask to mix the mixture.

. Equalise the pressure by opening the stopper as required.

. Continue shaking until there is no ‘whistle’ sound

. To collect the water in the lower layer, open the stopper and place a beaker under the spout

. Use another beaker to collect the desired organic layer

. Shake the liquid with some drying agent

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15
Q

Name 2 drying agents.

A

Magnesium sulphate

And

Calcium chloride

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16
Q

How is a drying agent used?

A

. Add a sealed drying agent to the organic layer

. If the drying agent forms clumps add some more until they are moving freely

. Use gravity filtration to collect the dry product

. Filtrate is the product

17
Q

What does re-distillation mean?

A

When a liquid is purified by using multiple distillations,.

18
Q

What are the 3 key steps to purify an organic solid?

A
  1. Filtration under reduced pressure
  2. Recrystallisation
  3. Measurement of melting points
19
Q

Define a radical

A

An atom or groups of atoms with an unpaired electron

20
Q

What conditions are needed for alkanes to react with halogens?

A

Sunlight (UV radiation)

Halogen (e.g. Cl2, Br2

21
Q

What is the type of mechanism for the reaction of alkanes with halogens?

A

Free radical substitution

22
Q

What is the organic product formed when alkanes and halogens react together?

A

Haloalkane

23
Q

What are the 3 stages in free radical substitution?

A

Initiation

Propagation

Termination

24
Q

What conditions are needed for the hydrogenation of alkenes?

A

Hydrogen

Nickel catalyst at 423K

25
Q

What type of reaction is the hydrogenation of alkenes? And what organic product is formed?

A

Addition reaction

Alkane formed

26
Q

What conditions are needed for alkenes to react with halogens?

A

Halogen (Chlorine/bromine)

Room temp