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Chemistry > Synthesis > Flashcards

Synthesis Flashcards

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1
Q

Alkene to alkane

A
  • hydrogenation
  • 150 degrees
  • nickel catalyst
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2
Q

Alkene to dihaloalkane

A
  • Br2/Cl2 etc used

- draw the reaction mechanism

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3
Q

Alkene to alcohol

A
  • hydration
  • steam
  • high temp and pressure (300 degrees 65 atm)
  • hot phosphoric acid catalyst
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4
Q

Alkene to haloalkane

A
  • HBr/HCl used

- draw mechanism

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5
Q

Alkene to polymer

A
  • addition polymerisation

- monomers have the pi bond broken and the electrons from each pi bond make a sigma bond with another monomer

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6
Q

Alcohol to aldehyde

A
  • Oxidise a primary alcohol
  • acidified potassium dichromate
  • distillation
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7
Q

Alcohol to carboxylic acid

A
  • oxidise a primary alcohol
  • acidified potassium dichromate
  • reflux
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8
Q

Alcohol to ketone

A
  • oxidise a secondary alcohol
  • acidified potassium dichromate
  • heat
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9
Q

Alcohol to alkene

A
  • dehydration
  • elimination reaction
  • heated with strong acid e.g conc H2SO4
  • 170 degrees
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10
Q

Alcohol to haloalkane

A
  • halide substitution
  • ROH + HX –> RX + H2O
  • acid catalyst such as H2SO4
  • mixture is warmed
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11
Q

Haloalkane to alcohol

A
  • nucleophilic substitution
  • hydrolysis
  • water often used, or NaOH
  • draw reaction mechanism
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12
Q

Alkanes to haloalkanes

A 
- radical substitution
Initiation: 
- CL2 --> 2Cl'
Propagation: 
- CH4 + Cl' --> 'CH3 + HCl
- 'CH3 + Cl2 --> CH3Cl + Cl'
Termination:
- 2Cl' --> Cl2
- 2'CH3 --> C2H6
- 'CH3 + Cl' --> CH3Cl
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13
Q

Benzene to nitrobenzene

A
  • nitration
  • substitution reaction
  • reagent is concentrated nitric acid
  • sulfuric acid catalyst
  • C6H6 + HNO3 –> C6H5NO2 + H2O
  • reflux
  • draw mechanism
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14
Q

benzene to halobenzene

A
  • halogenation
  • halogen carrier is required as the benzene ring is too stable
  • iron halides or aluminium halides are used to generate a positive halogen ion
  • For chlorination, AlCl3 or FeCl3
  • For bromination, AlBr3 or FeBr3
  • Br2 + FeBr3 –> Br+ + FeBr4- (bromide ion acts as electrophile)
  • draw reaction mechanism
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15
Q

benzene to alkylbenzene

A
  • friedel-crafts
  • electrophilic substitution
  • haloalkane mixed with halogen carrier which acts as a catalyst and is regenerated at the end
  • mixture of products made that can be separated using fractional distillation or chromatography.
  • draw mechanism
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16
Q

Benzene to ketone

A
  • friedel-crafts
  • acylation
  • Acyl chloride used as halogen carrier
  • 60 degrees under reflux
  • AlCl3 catalyst
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17
Q

phenol to bromophenol

A
  • triple substitution reaction
  • reaction with bromine water
  • C6H5OH + 3Br3 –> C6H2Br3OH + 3 HBr
  • product is a white precipitate of 2,4,6-tribromophenol
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18
Q

Phenol to nitrophenol

A
  • single substitution reaction with dilute nitric acid at room temperature
  • mixture of 2-nitrophenol and 4-nitrophenol (2- and 4- directing effect)
  • NO catalyst needed
  • If conc nitric acid is used, a triple substitution reaction occurs forming 2,4,6-trinitrophenol
  • C6H5OH + HNO3 –> C6H4(NO2)OH + H2O
19
Q

Carbonyl to alcohol

A
  • reduction
  • NaBH4 used as reducing agent, source of hydride ion, H-
  • CH3COC3H7 + 2[H] –> CH3CH(OH)C3H7
  • draw mechanism
20
Q

esterification

A
  • carboxylic acid and alcohol
  • gently heated
  • sulfuric acid catalyst
  • reversible reaction with slow rate of reaction
  • ester is separated using distillation
  • To prepare large esters, reflux used and then separated using fractional distillation
21
Q

Acid anhydride with alcohol

A
  • produces an ester and a carboxylic acid
  • irreversible so produces a higher yield than using a carboxylic acid
  • rate is slow but can be increased by warming mixture
  • ethanoic anhydride+ methanol –> methyl ethanoate + ethanoic acid
22
Q

Hydrolysis of esters in acidic conditions

A
  • when refluxed with catalyst of hot aqueous acids such as dilute H2SO4 or dilute HCl, ester decomposes reversibly into an alcohol and a carboxylic acid.
  • propyl ethanoate + water <=> ethanoic acid + propan-1-ol
23
Q

Hydrolysis of esters in alkaline conditions

A
  • When refluxed with hot aqueous alkali such as KOH or NaOH, decomposes into alcohol and a carboxylate salt
  • irreversible reaction
  • this is saponification (to make soaps)
  • ethyl propanoate + NaOH –> sodium propanoate + ethanol
24
Q

Acyl chloride to ester

A
  • reacted with an alcohol
  • not reversible so higher yield than using a carboxylic acid
  • CH3COCl + CH3CH2OH –> CH3COOCH2CH3 + HCl
25
Q

Phenol to ester

A
  • React with an acyl chloride
  • can’t use a carboxylic acid
  • however reaction is violent and produces corrosive fume of HCl
26
Q

Acyl chloride to carboxylic acid

A
  • small acyl chloride added to water
  • quickly hydrolyses
  • very exothermic and fumes of HCl are given off
  • CH3COCl + H2O –> CH3COOH + HCl
27
Q

Acyl chloride to primary amide

A
  • reacts with ammonia
  • CH3COCl + 2NH3 –> CH3CONH2 + NH4Cl
  • ethanoyl chloride + ammonia –> ethanamide + ammonium chloride
28
Q

Acyl chloride to secondary amide

A
  • Acyl chloride reacts with a primary amide to produce a secondary amide
  • nitrogen atom will have two organic groups attached so it is N-substituted
  • CH3COCl + CH3CH2NH2 –> CH3CONHCH2CH3 + HCl
  • ethanoyl chloride + ethanamide –> N-ethylethanamide + HCl
29
Q

Preparation of an acyl chloride

A

-OH group on a carboxylic acid must be substitued for a chlorine atom
CH3COOH + SOCl2 –> CH3COCl + SO2 HCl
Acyl chloride is separated using distillation

30
Q

Reaction of amine with dilute inorganic acid (HCL and HNO3)

A

An alkylammonium salt is made
CH3CH2NH2 + HCl –> CH3CH2NH3+Cl-
If nitric acid is used:
CH3CH2NH2 + HNO3 –> CH3CH2NH3+NO3-

31
Q

Preparation of a primary aliphatic amine

A

A haloalkane, ammonia and ethanol are heated together. Reflux can’t be used because ammonia is so volatile and would escape out of the condenser.
Stage 1: CH3CH2Cl + NH3 –> CH3CH2NH3Cl
Stage 2: Additional ammonia reacts, CH3CH2NH3Cl + NH3 <=> CH3CH2NH2 + NH4Cl

32
Q

How would you increase the yield of a primary aliphatic amine?

A

The reaction is reversible so excess ammonia will drive the reaction to the right and increase the yield of the desired primary amine product

33
Q

Preparation of a secondary aliphatic amine

A

Haloalkane and primary amine
Additional substitution of the hydrogen atoms on the nitrogen atom can occur
CH3CH2Cl + CH3CH2NH2 <=> (CH3CH2)2NH + HCl

34
Q

Preparation of a tertiary aliphatic amine

A

Further substitution

CH3CH2Cl + (CH3CH2)2NH <=> (CH3CH2)3N + HCl

35
Q

Haloalkane + tertiary amine

A

Quaternary ammonium salt is produced
Each hydrogen on the ammonium ion has been replaced by an alkyl chain
CH3CH2Cl + (CH3CH2)3N <=> (CH3CH2)4N+Cl-

36
Q

Preparation of an aromatic amine

A

Nitrobenzene reduced to phenylamine
Reducing agent is a mixture of tin and hydrochloric acid
Reflux at 100 degrees
After a while strong alkali such as NaOH is added to undergo a neutralisation reaction and to remove excess HCl and produce the amine.
C6H5NO2 + 6[H] –> C6H5NH2 + 2H2O

37
Q

How is the aromatic amine separated?

A

multi stage process including steam distillation, solvent extraction and further distillation

38
Q

Formation of a polyester

A

Condensation polymerisation
reaction of a dicarboxylic acid and a diol
ester link forms between molecules
polyester repeat unit - [-O-R-O-CO-R’-CO-]n

39
Q

Formation of a polyamide

A

Condensation polymerisation
Reaction of a dicarboxylic acid and a diamine
Amide link forms between molecules
repeat unit - [-NH-R-NH-CO-R’-CO-]n

40
Q

Haloalkane to nitrile

A 
Nucleophilic substitution
Haloalkane mixed with potassium cyanide
Heated under reflux
Ethanol solvent
CH3CH2Br + KCN --> CH3CH2CN + KBr
41
Q

Cyanide to hydroxynitrile

A

Carbonyl
Hydrogen cyanide can be used to generate cyanide nucleophile
Nucleophilic addition
Cyanide ion will be attracted to carbon of C=O bond and will form a covalent bond. pi bond opens and the oxygen accepts the extra pair of electrons. This means the negative oxygen can accept a proton and become a hydroxyl group. Racemic mixture made when an aldehyde or an asymmetric keytone is used.
Draw mechanism

42
Q

Nitrile to amine

A

Reduction
Hydrogen can react directly with a nitrile to form a primary aliphatic amine
Two hydrogen atoms are added to the nitrogen atom of the nitrile group
Transition metal catalyst such as nickel
Heated to 150 degrees at raised pressure
RCN + 2H2 –> RCH2NH2

43
Q

Reduction of nitrile using a reducing agent

A

Reducing agent of LiAlH4

RCN + 4[H] –> RCH2NH2

44
Q

Nitrile to carboxylic acid

A

Acid hydrolysis
Reflux
Dilute HCl
CH3CN + 2H2O + HCl –> CH3COOH + NH4Cl

Chemistry (6 decks)

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