C16 - Organic Synthesis Flashcards

1
Q

What is the equipment for heating under reflux?

A
  • Round-bottom flask
  • Condenser
  • Rubber tubing
  • Stand and clamp
  • Heat source
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2
Q

What is reflux?

A

The continual boiling and condensing of a reaction mixture back to the original container to ensure that the reaction takes place without the contents of flask boiling dry.

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3
Q

Why is reflux used for organic reactions?

A

Organic reactions (compounds involving carbon) are slow and are usually flammable and volatile so have low boiling points.
Therefore if you heat them with a Bunsen burner they’ll evaporate or catch fire before they can react.
Reflux means that the liquid continuously boils, evaporates and condenses back to the flask, giving them time to react. And safer as avoids naked flames.

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4
Q

What is distillation?

A

Gently heating a mixture in a distillation apparatus, the substance will evaporate out of the mixture in order of increasing boiling point.

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5
Q

Equipment needed for distillation:

A
  • Round-bottom flask
  • Condenser
  • Rubber tubing
  • Heat source
  • Stand and clamp
  • Screw-cap adaptor
  • Receiver adaptor
  • Thermometer
  • Still head
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6
Q

What is distillation commonly used for?

A

To separate a pure liquid from its impurities. As you know it’s boiling point

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7
Q

Why is redistillation used?

A

If a product and its impurities have different boiling points, then redistillation can be used to separate them. Your heating an impure product instead of a reaction mixture in distillation.

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8
Q

How does redistillation work?

A

When the liquid you want boils, you place a flask at the open end of the confessor ready to collect your product. When the the thermometer shows the tempreture is changing, put another flask at the condenser as a different liquid is about to be delivered.

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9
Q

What is a synthetic route?

A

A synthetic route shows how you get from one compound to another. It shows all the reactions with immediate products, and the reagents needed for the reaction.

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10
Q

What does separation do?

A

If a product is insoluble in water then you can use separation to remove any impurities that do dissolve in water such as water (e.g salts or alcohols).

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11
Q

Explain how separation works?

A
  1. Once the reaction to form a product has formed pour this into a separating funnel and add water.
  2. Shake the funnel and then allow it to settle. The organic layer and the aqueous layer (which contains water soluble impurities), don’t mix and separate into two distinct layers.
  3. You can then open the tap and run each layers into seperate containers.
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12
Q

What is the problem with using separation to purify a product?

A

The organic (desired) layer will end up containing trace amounts of water, so has to be dried.

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13
Q

How do you get rid of the trace of water in the organic layer in separation?

A

Add an anhydrous salt, like magnesium sulphate (MgSO4) or calcium chloride (CaCl2). The salt is a drying agent so binds to any water present to become hydrated.

When you first add the salt it will be lumpy however keep adding it to the solution until you swirl the mixture. Then filter the mixture to remove the solid drying agent.

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14
Q

What is a functional group, properties and typical reactions for an Alkane?

A

Functional Group - C—C

Properties - Non-polar, unreactive

Typical Reactions - Radical Substitution

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15
Q

What is a functional group, properties and typical reactions for an Alkene?

A

Functional Group - C=C

Properties - Non-polar, electron-rich double bond.

Typical Reactions - Electrophilic addition

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16
Q

What is a functional group, properties and typical reactions for an Alcohol?

A

Functional Group - C—OH

Properties - Polar C—OH bond. Lone pair on O acts as nucleophile.

Typical Reactions - Nucleophilic Substitution and Dehydration/Elimination.

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17
Q

What is a functional group, properties and typical reactions for a Haloalkane?

A

Functional Group - C—X

Properties - Polar C—X bond

Typical Reactions - Nucleophilic Substitution

18
Q

What is a functional group, properties and typical reactions for an Aldehyde and a Ketone?

A

Functional Group - C=O

Properties - Polar C=O bond

Typical Reactions - Aldehydes will oxidise

19
Q

What is a functional group, properties and typical reactions for a Carboxylic Acid?

A

Functional Group - —COOH

Properties - Electron deficient carbon centre

Typical Reactions - Esterification

20
Q

If your asked how to make one compound from another in the exam, what must you make sure to include?

A
  1. Any special procedures, such as reflexing.
  2. The conditions needed, e.g high temperature or pressure, presence of a catalyst.
21
Q

What is the synthetic route for alkane to haloalkanes?

A

Halogen (X2), UV light.

Substitution reaction

22
Q

What is the synthetic route for alkene to alkane?

A

H2, Nickel Catalyst.

Addition reaction

23
Q

What is the synthetic route for alkene to haloalkanes?

A

Hydrogen Halide (HX).

Addition reaction

24
Q

What is the synthetic route for haloalkane to alcohol and back (alcohol to haloalkane)?

A

H to A - warm NaOH or KOH, Water (H2O), reflux. Substitution reaction.

A to H - Sodium Halide (NaX) and H2SO4 (Sulphuric Acid).

25
Q

What is the synthetic route for alkene to alcohol and back (alcohol to alkene)?

A

Alkene to Alcohol - Steam (H2O (g) ), H3PO4 catalyst, high temperature and pressure. Addition reaction

Alcohol to Alkene - Concentrated H2SO4 or H3PO4, heat. Elimination reaction.

26
Q

What is the synthetic route for a primary alcohol to aldehyde to carboxylic acid?

A

Alcohol to aldehyde - K2Cr2O7 (potassium dichromate)/H2SO4 (sulfuric acid), distillation. Oxidation reaction

Aldehyde to carboxylic acid - K2Cr2O7 (potassium dichromate)/H2SO4 (sulfuric acid), reflux. Oxidation reactions.

27
Q

What is the synthetic route for secondary alcohol to ketone?

A

K2Cr2O7 (potassium dichromate)/H2SO4 (sulfuric acid), reflux. Oxidation reaction.

28
Q

What can alkane go to on a synthetic route?

A

Haloalkane (only).

29
Q

What can alkene go to on a synthetic route?

A

Alkane, Haloalkane, Alcohol, Dihaloalkane.

30
Q

What can Haloalkane go to on a synthetic route?

A

Alcohol (only).

31
Q

What can alcohol go to on a synthetic route?

A

Haloalkane
Aldehyde (primary alcohol)
Ketone (secondary alcohol)
Alkene

32
Q

What can aldehyde go to on a synthetic route?

A

Carboxylic Acid

33
Q

What do you need to include when converting a starting molecule to the target molecule?

A
  1. Identify the functional groups in your starting and target molecules.
  2. Identify the intermediate that links the starting and target molecules.
  3. State the reagents and conditions for each step.
34
Q

State the reagents and conditions for the two-stage synthesis of propanol from 1-chloropropane.

. Step 1 Step 2
CH3CH2CH2Cl —> Intermediate —> CH3CH2COH

A

Step 1: Requires NaOH (aq) under reflux to turn an Haloalkane to a primary alcohol.

Step 2: Requires Potassium Dichromate and sulfuric acid under distillation to turn a primary alcohol into a aldehyde.

35
Q

What does the term of target molecule mean?

A

The compound that the chemist is attempting to prepare by organic synthesis.

36
Q

State the reagents and conditions for the two-stage synthesis of butanone from but-2-ene. State the functional groups and reaction as well it changes to.

A

Stage 1: A ketone (target molecule) can be made form the oxidation of a secondary alcohol.
Reagents- steam, H2O (g).
Conditions- Acid Catalyst (H3PO4 or H2SO4)

Stage 2: A secondary alcohol can be made by the hydration of an alkene (starting molecule).
Reagents- Potassium Dichromate (VI) and Sulfuric Acid
Conditions- Reflux

37
Q

Predict the reagents and conditions for each of each step.

. Step 1 Step 2 Step 3
CH2=CHCHBrCH2 —> CH3CH2CHBrCH3 —> CH3CH2CH(OH)CH3 —> CH3CH2COCH3

A

Step 1: Requires H2 and Nickel catalyst to convert the alkene into an alkane.

Step 2: Requires NaOH (aq) and reflux to covert the Haloalkane into an alcohol.

Step 3: Requires K2Cr2O7 and H2SO4 and reflux to convert the secondary alcohol into a ketone.

38
Q

What is an addition reaction?

A

A reaction in which a reactant is added to an unsaturated molecule to make one saturated molecule.

39
Q

What is a substitution reaction?

A

A reaction in which one atom or group of atoms is replaced by another atom or groups of atoms.

40
Q

What is an elimination reaction?

A

The removal of a molecule from a saturated molecule to make an unsaturated molecule.

41
Q

What is the synthetic route for alkene to dihaloalkane?

A

Halogen (X2), 20°c. Addition reaction