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Organic synthesis Flashcards

1
Q

alkane –> halogenoalkane

A

Free radical substitution
UV light
Br2 or Cl2

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2
Q

alkene –> alkane

A

Hydrogenation (irreversible)
Hydrogen
150C
Nickel catalyst

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3
Q

alkene –> dihalogenoalkane

A

Electrophilic addition
Halogen at room temp (eg Br2)

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4
Q

alkene –> alcohol

A

Electrophilic addition
Steam (H2O)
H3PO4
300C
60-70atm

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5
Q

alcohol –> alkene

A

Dehydration/elimination
Heat w/ conc. H3PO4

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6
Q

alkene –> halogenoalkane

A

Electrophilic addition
Hydrogen halide (eg HBr)
Room temperature

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7
Q

Halogenoalkane –> alkene

A

Elimination
Alcoholic (ethanolic) KOH/NaOH
Heat under reflux

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8
Q

alcohol –> ketone

A

Oxidation
Secondary alcohol
Heat under reflux
Acidified potassium dichromate (K2CrO7)

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9
Q

ketone –> secondary alcohol

A

Reduction
LiAlH4 in dry ether

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10
Q

first/secondary alcohol –> chloroalkane

A

Halogenation
PCl5

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11
Q

tertiary alcohol –> chloroalkane

A

Halogenation
Shake with conc. HCl

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12
Q

alcohol –> bromoalkane

A

Halogenation
KBr
50% conc sulphuric acid
Room temp

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13
Q

alcohol –> iodoalkane

A

Halogenation
Red phosphorus
Iodine
Heat under reflux

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14
Q

aldehyde –> primary alcohol

A

Reduction
LiAlH4 in dry ether

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15
Q

carbonyl (aldehyde/ketone) –> hydroxynitrile

A

KCN
Acidic conditions (eg with H2SO4)

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16
Q

Why are salts formed by carboxylic acid useful for making buffer systems?

A

Salts formed by carboxylic acids are (usually) highly soluble in water and can be a useful source of conjugate bases for making buffer systems

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17
Q

carboxylic acid + metal –> ?

A

Metal carbonate (salt) + hydrogen

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18
Q

carboxylic acid + alkali –> ?

A

Metal carboxylate (salt) + water

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19
Q

carboxylic acid + metal carbonate –> ?

A

Metal carboxylate (salt) + carbon dioxide + water

20
Q

carboxylic acid + metal oxide –> ?

A

Metal carboxylate (salt) + water

21
Q

carboxylic acid –> primary alcohol

A

Reduction
LiAlH4 in dry ether

22
Q

carboxylic acid –> acyl chloride

A

Nucleophilic substitution
PCl5
Cold temperature to room temperature

23
Q

carboxylic acid + alcohol –> ester

A

Condensation/esterification
Heat under reflux
Conc. H2SO4 catalyst

24
Q

ester –> carboxylate ion + alcohol

A

Alkaline hydrolysis
Warm
Aqueous alkaline conditions

25
Q

ester –> carboxylate ion + alcohol

A

Acid hydrolysis
Warm
Aqueous acidic conditions

26
Q

acyl chloride –> carboxylic acid

A

Nucleophilic addition-elimination
H2O
Room temperature

27
Q

acyl chloride –> ester

A

Nucleophilic addition-elimination/esterification (ester formed has a sweet, fruity smell)
Alcohol at room temperature

28
Q

acyl chloride –> amide

A

Nucleophilic addition-elimination
Ammonia

29
Q

acyl chloride –> secondary amide

A

Nucleophilic addition-elimination
Primary amine

30
Q

benzene –> nitrobenzene

A

Electrophilic substitution/nitration
Conc. nitric acid (–>nitronium ion)
Conc. sulphuric acid catalyst

31
Q

benzene –> aromatic ketone

A

Electrophilic substitution/Friedel crafts acylation
Acyl chloride
AlCl3 catalyst and warm

32
Q

benzene –> alkylbenzene

A

Electrophilic substitution/Friedel Crafts alkylation
Halogenoalkane
Warm
AlCl3 or AlBr3 catalyst

33
Q

nitrile –> primary amine

A

Reduction/hydrogenation
Reducing agent (LiAlH4 in dry ether or H2 with nickel catalyst)

34
Q

nitroarene –> phenylamine

A

Reduction
Conc. HCl (followed by NaOH)
Tin catalyst

35
Q

Dicarboxylic acid + diol –> polyester

A

Condensation polymerisation

36
Q

phenol –> 2,4,6-tribromophenol

A

Electrophilic substitution/bromination

37
Q

amine + acid –> ?

A

Alkyl ammonium salt

38
Q

amine + water –> ?

A

Alkyl ammonium ion + hydroxide

39
Q

dicarboxylic acid + diamine –> polyamide

A

Condensation polymerisation

40
Q

amino acid –> polyamide/polypeptide

A

Condensation polymerisation

41
Q

alkane combustion

A

Combustion
Alkane + oxygen (excess) –> CO2 + H2O

42
Q

halogenoalkane –> alcohol

A

Nucleophilic substitution/hydrolysis
NaOH
Heat under reflux, aq

43
Q

halogenoalkane –> nitrile

A

Nucleophilic substitution
NaCN or KCN
Heat under reflux
Ethanolic conditions

44
Q

halogenoalkane –> amine

A

Nucleophilic substitution
Ammonia
Heat
Ethanolic conditions (or else alcohol is likely to form instead)

45
Q

halogenoalkane –> alcohol

A

Nucleophilic substitution
KOH
Heat under reflux
Aqueous conditions

Chemistry (8 decks)

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