4 Synthetic Routes Flashcards

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1
Q

Haloalkane to alcohol

A

NaOH (aq) (or water or ammonia???)
Reflux
(Halogen is replaced by -OH. Makes Sodium halide)

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2
Q

Alkane to haloalkane

A
Halogen/UV
Haloalkane and hydrogen halide
E.g. bromomethane and HBr
Radical substitution 
Initial stage
Propagation
Termination
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3
Q

Alkene to haloalkane

A

Hydrogen halide or halogen
Electrophilic addition
Curly arrow from double bond to electropositive atom. Single bond to electroneg atom.

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4
Q

Alkene to alkane

A

H2
Ni catalyst
423Kelvin (150oC)

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5
Q

Alkene to alcohol

A

H2O(g) (steam)
H3PO4 catalyst
Hydration

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6
Q

Alcohol to haloalkane

A

Sodium halide
H2SO4
Substitution reaction
Sodium halide + sulfuric acid -> NaHSO4 + Hydrogen halide
The hydrogen halide produced is used in reaction
Alcohol + hydrogen halide -> haloalkane + H2O
Produces water

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7
Q

Alcohol to alkene

A

Dehydration
Water molecule removed
Heated under reflux in presence of phosphoric acid catalyst

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8
Q

Primary alcohol to carboxylic acid

A
K2Cr2O7/H2SO4 
Heated under Reflux 
Oxidation
Alcohol + 2[O] -> carboxylic acid + H2O
Produces water
The dichromate ions change colour from orange to green
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9
Q

Primary Alcohol to aldehyde

A
K2Cr2O7/H2SO4
Distilled
Oxidation
Alcohol + [O] -> aldehyde + water
Produces water
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10
Q

Secondary alcohol to ketone

A
K2Cr2O7/H2SO4
Heated under reflux
Oxidation
Alcohol + [O] -> Ketone + water
Produces water
The dichromate ions change colour from orange to green
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11
Q

haloalkane to nitrile

A

NaCN

ethanol

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12
Q

haloalkane to amine

A

NH3

ethanol

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13
Q

primary alcohol to ester

A

carboxylic acid

conc H2SO4

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14
Q

nitrile to amine

A

H2

Ni catalyst

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15
Q

nitrile to carboxylic acid

A

H2O
HCl
heat
forms carboxylic acid and NH4Cl

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16
Q

carboxylic acid to ester

A

alcohol

conc H2SO4

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17
Q

carboxylic acid to acyl chloride

A

SOCl2

produces acyl chloride + SO2(g) + HCl(g)

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18
Q

aldehyde to primary alcohol

A

NaBH4/H2O

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19
Q

aldehyde to carboxylic acid

A

K2CR2O7/H2SO4

reflux

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20
Q

aldehyde to hydroxynitrile

A

HCN

H2SO4/NaCN

21
Q

ester to carboxylic acid and alcohol

A

dil acid hydrolysis
H+/H2O
heat

22
Q

ester to sodium salt of COOH and alcohol (carboxylate)

A

NaOH/H2O
alkaline hydrolysis
heat

23
Q

acyl chloride to ester

A

alcohol

24
Q

acyl chloride to carboxylic acid

A

H2O

25
Q

acyl chloride to primary amide

A

NH3

26
Q

acyl chloride to secondary amide

A

primary amine

27
Q

benzene to nitrobenzene

A

HNO3
H2SO4
50oC

28
Q

nitrobenzene to phenylamine

A

Sn/conc HCl

NaOH?????

29
Q

phenylamine to tribromophenylamine

A

Br2

30
Q

benzene to bromobenzene

A

Br2

FeBR3

31
Q

benzene to chlorobenzene

A

Cl2

AlCl3

32
Q

benzene to methylbenzene

A

CH3Cl

AlCl3

33
Q

benzene to benzene ketone ??

C6H5COCH3

A

CH3COCl

AlCl3

34
Q

phenol to nitrophenol

A

dil HNO3

35
Q

phenol to sodiumphenoxide

A

NaOH(aq)

36
Q

phenol to tribromophenol

A

Br2

37
Q

nitrobenzene to bromonitrobenzene

A

Br2
FeBr3
high temp

38
Q

ROH + NaCl + H2SO4 –>

A

RCl + NaHSO4 + H2O

39
Q

water in and out of condenser

A

water in at bottom

40
Q

RCN + acid

A

RCOOH

41
Q

MP of impure compound

A

lower than MP of pure compound

42
Q

reason for heating under reflux

A

to prevent any substances escaping

43
Q

haloalkane + H2O (+AgNO3 + ethanol)

A

alcohol + AgX

44
Q

radical substitution limitations

A

further substitution

substitution at diff positions on chain

45
Q

homologous series

A

same functional groups, diff carbon chain length

each successive member differs by CH2

46
Q

anhydrides and alcohol

A

ester

anhydrides dont react w carboxylic acids

47
Q

kekule and delocalised model similarities

A

overlap of p orbitals

pi ring above and below

48
Q

kekule and delocalised model differences

A

K has alternating pi bonds

delocalised has pi ring