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Chemistry > 3.3.14-Organic Synthesis > Flashcards

3.3.14-Organic Synthesis Flashcards

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1
Q

What needs to be thought of in organic synthesis

A
  • Reagents required
  • Presence of other functional groups
  • conditions required
  • rate of reaction
  • yield
  • atom economy
  • Costs , plants, chemicals
  • safety, toxicity, flammability
  • problems of purification
  • possibility of optical activity
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2
Q

Problems of chiral compounds

A

May not be as effective -higher dosage

Cause dangerous side effects

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3
Q

Consequences of chiral compounds

A

Isomers have to be separated to obtain effective result
Separation can be expensive and complicated
Non separation lead to larger dosage being used cause side effects

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4
Q

Solutions to chiral compounds

A

Use natural chiral compounds as starting
Use reactions that give specific isomers
Catalysts to give specific isomers
Enzyme or bacteria which are stereoselective

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5
Q

Thermal cracking reaction

A

Alkane to alkanes,alkenes

Need high T,high P

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6
Q

Catalytic cracking reaction

A

Alkane to alkenes and branched alkanes

High T , zeolite

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7
Q

Complete combustion

A

Alkanes to water and carbon dioxide

Need excess O2

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8
Q

Reaction of free radical substitution

A

CH4 to CH3Cl +HCl

Cl2 UV light

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9
Q

Alkene reaction hydrogenation

A

H2/Ni 150C

C2H4 to C2H6

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10
Q

Alkene reaction with Br2

A

C2H4 to CH2BrCH2Br

Br2 room temp
Electrophilic addition

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11
Q

Alkene reaction with HBr

A

C2H4 to CH3CH2Br

HBr room temp
Electrophilic addition

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12
Q

Alkene reaction with conc H2SO4

A

Alkene to CH3CH2-O-SO3H

Electrophilic addition
Conc H2SO4

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13
Q

Alkene reaction with H2O

A

C2H4 to CH3CH2OH

H3PO4 ,high T , high P
Hydration

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14
Q

What is the reaction when

CH3CH2-O-SO3H +H2O and what does it make

A

Hydrolysis

To make CH3CH2OH

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15
Q

CH3CH=CH2

To make CH3CH(OH)CH3

A

1) conc H2SO4
Electrophilic addition
2) H2O
Hydrolysis

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16
Q

CH3CH=CH2 to CH3CH(Br)CH3

A

HBr room temp electrophilic addition

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17
Q

Haloalkane to CH3CH2CN +KBr

A

KCN , ethanol

Nucleophilic substitution

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18
Q

Haloalkane to CH3CH2OH +NaBr

A

NaOH/KOH
Warm/aq
Nucleophilic substitution

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19
Q

Haloalkane to CH3CH2NH2

A

Ammonia
Ethanol/high p
Nucleophilic substitution

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20
Q

Haloalkane to CH2=CH2

A

KOH ethanol

Elimination

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21
Q

Nitrile to CH3CH2CH2NH2

A

LiAlH4
Ethoxyethane
Reduction

22
Q

Primary alcohol to Aldehyde

A

K2Cr2O7 / H+ distill off

Oxidation

23
Q

Primary alcohol to alkene

A

Conc H2SO4 180C

Dehydration/elimination

24
Q

Primary alcohol to R-COO- CH2CH3

A

R-COCl

Nucleophilic addition elimination

25
Q

Primary alcohol to CH3COOCH2CH3 + H2O

A

Ethanoic acid
Conc H2SO4
Esterification

26
Q

Secondary alcohol to CH3CHOCH3 (ketones)

A

K2CR2O7/H+

Oxidation

27
Q

Secondary alcohol to CH3CH=CH2

A

Conc H2SO4
180
Dehydration

28
Q

Carboxylic acid to CH3COONa +CO2+H2O

A

NaHCO3 room temp

Acid base

29
Q

Carboxylic acid to CH3COOR +H2O

A

ROH conc H2SO4

Esterification

30
Q

CH3COOR to CH3COONa + ROH

A

NaOH reflux

Hydrolysis

31
Q

Aldehydes to CH3CH(OH)CN

A

KCN
Add HCl in situ
Nucleophilic addition

32
Q 
CH3CH(OH)CN 
To CH3CH(OH)CH2NH2
A

LiAlH4
Ethoxyethane
Reduction

33
Q

Aldehyde to CH3COOH

A

Fehlings solution
Heat
Oxidation

34
Q

Aldehyde to CH3CH2OH

A 
NaBH4 aq,warm 
Reduction 
Or 
H2/Ni 150 
Reduction
35
Q

Ketone to (CH3)2C(OH)CN

A

HCN from KCN and HCl

Nucleophilic addition

36
Q

Ketone added fehlings solution

A

No reaction

37
Q

Ketone to CH3CH(OH)CH3

A 
NaBH4 
Nucleophilic addition 
Or 
H2/Ni 
150 
Reduction
38
Q

C6H6 to C6H6NO2

A

Conc HNO3 and conc H2SO4

Nitration

39
Q

C6H6 to C6H12

A

H2/Ni
150
Reduction

40
Q

C6H6 to C6H5COCH3 +HCl

A

CH3COCl /ALCl3

Electrophilic substitution

41
Q

Amino acid — H3N+CH2COOH

A

HCl

Acid base

42
Q

Amino acid to H2NCH2COO-

A

NaOH

Acid base

43
Q

Amino acid to H2nCH2COOCH3 +H2O

A

CH3OH
Conc H2SO4
Esterification

44
Q

Amino acid to CH3CONHCH2COOH

A

CH3COCl room temp

Acylation

45
Q

Amino to H2NCH2COHNCH2COOH

A

Amino acid

Condensation

46
Q

Test

Bromine water

A

Add Br 2
Tests for C=C
Orange to colourless positive

47
Q

Acidified K2CR2O7 test

A 
Heat K2Cr2O7/H+ 
Test for 
Primary, secondary alcohol 
Aldehydes 
Go orange to green
48
Q

Tollens reagent test

A

Warm AgNO3
NaOH and NH3
Aldehydes
Silver mirror

49
Q

Fehlings solution test

A

Fehlings A and B boil
Blue to brick red
Tests for aldehydes

50
Q

Hydrolysis followed by acidified AgNO3 year

A 
NaOH heat then add AgNO3 
Tests for haloalkane 
Cl - white 
Br- cream 
I - yellow
51
Q

Hydrolysis test

A

Add H20
Test for acyl chloride
Steamy misty fumes

Chemistry (29 decks)

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