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OFFICIAL OCR A-Level Chemistry > Chapter 28 - Organic Synthesis > Flashcards

Chapter 28 - Organic Synthesis Flashcards

Carbon-carbon bond formation, Further practical techniques, Further synthetic routes.

1
Q

R-CHO -> R-CH(OH)CN

Aldehyde to hydroxynitrile

A

NaCN / H+

Nucleophilic addition

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2
Q

RCH2CH2OH -> RCH=CH2

Primary alcohol to alkene

A

H2SO4 or H3PO4

Heated under reflux

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3
Q

RCOCl -> RCONH2

Acyl chloride to amide

A

NH3

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4
Q

CH2=CH2 -> CH3CH2Br

Alkene to haloalkane

A

Hydrogen Halide
Rapid addition
Room temperature

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5
Q

RCH2OH -> RCH2Br

Primary alcohol to haloalkane

A

Sodium halide
H2SO4
Heated under reflux
Hydrogen halide formed in situ

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6
Q

R’COOCH2R -> RCH2OH + R’COOH

Ester to alcohol and carboxylic acid

A

Dilute acid hydrolysis
Heated under reflux with dilute aqeuous acid
Broken down by water into two products

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7
Q

RCH2CN -> RCH2CH2NH2

Nitrile to amine

A

H2 / Ni

Reduction

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8
Q

RCOOH -> RCOCl

Carboxylic acid to acyl chloride

A

SOCl2

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9
Q

RCH2Br -> RCH2OH

Haloalkane to primary alcohol

A

NaOH(aq)

Heat under reflux

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10
Q

RCH2Br -> RCH2CN

Haloalkane to nitrile

A

NaCN

In ethanol

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11
Q

RCH2OH + R’COOH -> R’COOCH2R + H2O

Alcohol and carboxylic acid to ester and water

A

H2SO4 concentrated

Esterification

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12
Q

RCH2CN -> RCH2COOH

Nitrile to carboxylic acid

A

H2O / HCl

Hydrolysis

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13
Q

R’COOCH2R -> RCH2OH + R’COO- Na+

Ester to alcohol and sodium salt of carboxylic acid

A

Alkaline hydrolysis
Heated under reflux woth aqueous hydroxide ions
Broken down by water into products

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14
Q

R-CHO -> R-COOH

Aldehyde to carboxylic acid

A

K2Cr2O7 / H2SO4
Strong heat
Under reflux
Oxidation

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15
Q

R-CH=CH2 -> RCH2CH2OH

Alkene to primary alcohol

A

H3PO4 / H2O(g)

Hydration

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16
Q

R-CH2OH -> R-CHO

Primary alcohol to aldehyde

A

K2Cr2O7 / H2SO4
Gentle heating
Distill off
Oxidation

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17
Q

RCH2Br -> RCH2NH2

Haloalkane to primary amine

A

Haloalkane + NH3 (xs)
Salt + NaOH -> primary amine
Ethanol as solvent

18
Q

R’COCl -> R’COOCH2R

Acyl chloride to ester

19
Q

RCOCl -> RCOOH

Acyl chloride to carboxylic acid

20
Q

RCOCl -> RCONHR’

Acyl chloride to secondary amide

A

R’NH2

Primary amine

21
Q

R-CHO -> R-CH2OH

Aldehyde to primary alcohol

A

NaBH4 / H2O

Reduction

22
Q

Benzene to methylbenzene

A

CH3Cl/FeCl3

Alkylation

23
Q

Benzene to phenylethanone

A

CH3CClO/FeCl3

Acylation

24
Q

Phenylethanone to phenylethanol

A

NaBH4

Reduction

25
Q

Benzene to chlorobenzene

A

Cl2/AlCl3

Chlorination

26
Q

Benzene to bromobenzene

A

Br2/AlBr3

Bromination

27
Q

Benzene to nitrobenzene

A

HNO3/H2SO4
50°C
Nitration

28
Q

Nitrobenzene to phenylamine

A 
Sn/HCl
Heated under reflux
Forms ammonium salt
Ammonium salt reacts with NaOH
Phenylamine produced
Reduction
29
Q

Phenylamine to tribromophenylamine

30
Q

Phenol to 2-nitrophenol/4-nitrophenol

A

HNO3

Nitration

31
Q

Phenol to sodium salt of phenol

A

NaOH

Neutralisation

32
Q

Phenol to tribromophenol

A

Br2
Room temp
No catalyst
Bromination

33
Q

Alkene to alkane

A

H2/Ni

423K

34
Q

Secondary alcohol to ketone

A

K2Cr2O7/H2SO4

Heated under reflux

35
Q

Primary amine to secondary amine

A

Primary amine + CH3Br
Ethanol as solvent
Salt product + NaOH forms amine

36
Q

Amino acid to ester

A

Alcohol + amino acid
H2SO4
NaOH

37
Q

Two monomers to polyamide

A

Dioic acid

Diamide

38
Q

One monomer to poly amide

A

Amino acid

39
Q

Two monomers to polyester

A

Diol

Dicarboxylic acid

40
Q

Draw a labelled diagram to show how you would safely set up apparatus for distillation and describe
a method to obtain a pure sample of cyclohexanone from the distillate? (6)

A 
Includes following components:
-distillation flask
-heat source
-thermometer at outlet (bulb level with outlet)
-still-head
-water condenser (correct direction of water
flow)
-receiving vessel
-open system.

Further purification
-Shake and leave to settle in a separating
funnel;
-Separate layers by tapping off;
-Add (a small amount of) anhydrous
magnesium sulfate/anhydrous calcium chloride
to organic layer (in a dry conical flask);
-(Re)distil the organic layer;
-Collect fraction distilling at (between 150 °C
and) 156 °C.

41
Q

Describe a method to obtain a pure sample of 3-nitrobenzoic acid from the impure solid,
determine the percentage yield and check its purity (6)

A 
1. Purification
 Recrystallisation
 Dissolve impure solid in minimum volume of hot
water/solvent
 Cool solution and filter solid
 Wash with cold water/solvent and dry
  1. Percentage yield
    - do calculation
3. Checking purity
Obtain melting point
 Compare to known values
 Pure sample will have a (sharp) melting point very
close to data book value

OFFICIAL OCR A-Level Chemistry (35 decks)

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