Organic synthesis Flashcards
Exam technique for answering synthesis questions?
6 steps?
- Identify functional groups
- Look for difference between start and end molecules of the pathway and deduce how they might have happened
- Identify reagents that will add or remove atoms/groups of atoms to account for the differences
- Identify conditions for said reagents
- Use nature of reagent eg: nucleophile to decide on type of mechanism/reaction
- Don’t forget other products of reactions
Give the reagent needed to form an alkane from an alkene
H2
Give the reagent needed to form a haloalkane from an alkane
A halogen (X2)
Give the conditions needed to form an alkane from an alkene
2
Over Nickel catalyst
At 200*C
Give the conditions needed to form a haloalkane from an alkane
1
UV light
Give the reagent needed to form a haloalkane from an alkene?
Halogen halide (HX)
Give the conditions needed to form a haloalkane from an alkene?
1
Room temperature
Name the type of reaction to form a haloalkane from an akene
Nucleophilic Addition
Name the type of reaction to form a haloalkane from an alkane
Free Radical Substitution
Name the type of reaction to form an alkane from an alkene
Free Radical/Catalytic Addition
Give the reagent needed to form an amine from a haloalkane
Conc. NH3
Give the conditions needed to form an amine from a haloalkane
2
Heat
in a sealed tube
Name the type of reaction to form an amine from a haloalkane
Nucleophilic Substitution
Give the reagent needed to form a nitrile from a haloalkane
KCN
Give the conditions needed to form a nitrile from a haloalkane
3
Ethanolic solution
Reflux
Heat
Name the type of reaction to from a nitrile from a haloalkane
Nucleophilic Substitution
Give the reagent needed to form an amide from an amine
2
Acyl chloride or acid anhydride
Give the conditions needed to form an amide from an amine
1
Reflux
Name the type of reaction to form an amide from an amine
Acylation
Give the reagent needed to form an amine from a nitrile
H2
or LiAlH4
Give the conditions needed to form an amine from a nitrile
Nickel catalyst
200*C
Name the type of reaction to form an amine from a nitrile
Reduction / Electrophilic addition
Give the reagent needed to form an alcohol from a haloalkane
NaOH (aq)
Give the conditions needed to form an alcohol from a haloalkane
2
Reflux, warm
Name the type of reaction to from an alcohol from a haloalkane
Nucleophilic Substitution
Give the reagent needed to form an alkene from a haloalkane
Conc. KOH
Give the conditions needed to form an alkene from a haloalkane
2
Hot
Ethanolic
Name the type of reaction to form an alkene from a haloalkane
Elimination
Give the reagent needed to form an alkene from an alcohol
Conc. H2SO4
Give the conditions needed to form an alkene from an alcohol
2
Reflux, 180*C
Name the type of reaction to form an alkene from an alcohol
Elimination
Give the reagent needed to form an alcohol from an alkene
Conc, H3PO4
Give the conditions needed to form an alcohol from an alkene
3
Steam High temp (300*C) High pressure (60 atm)
Name the type of reaction to form an alcohol from an alkene
Electrophilic Addition
Give the reagent/conditions needed to form an alkyl hydrogensulphate from an alkene
Conc, H2SO4
Name the type of reaction to form an alkyl hydrogensulphate from an alkene
Addition
Give the reagent/conditions needed to form an alcohol from an alkyl hydrogensulphate
H2O
Warm
Give the reagent needed to form an aldehyde from a primary alcohol
K2Cr2O7
Give the conditions needed to form an aldehyde from a primary alcohol
3
distill or reflux?
H+ so need H2SO4
Heat
Distill
Name the type of reaction to form an aldehyde from a primary alcohol
Oxidation
- Give the reagent needed to form a primary alcohol from an aldehyde
Aqueous NaBH4
- Give the conditions needed to form a primary alcohol from an aldehyde
heat
ethanolic
Name the type of reaction to form a primary alcohol from an aldehyde
Reduction
Give the reagent needed to form a ketone from a secondary alcohol
K2Cr2O7
Give the conditions to form a ketone from a secondary alcohol
3
distill or reflux?
H+ so need H2SO4
Heat
Reflux
Name the type of reaction to form a ketone from a secondary alcohol
Oxidation
- Give the reagent needed to form a secondary alcohol from a ketone
NaBH4
- Give the conditions needed to form a primary alcohol from an aldehyde
dry ether
- Give the conditions needed to form a secondary alcohol from a ketone
heat
ethanolic
- Give the reagent needed to form a secondary alcohol from a ketone
LiAlH4
- Give the conditions needed to form a secondary alcohol from a ketone
dry ether
Give the reagent/conditions needed to form a 2-hydroxynitrile from a ketone
HCN
Name the type of reaction to form a 2-hydroxynitrile from a ketone
Nucleophilic addition
Give the reagent needed to form a carboxylic acid from an aldehyde
3 options
K2Cr2O7 or Tollens reagent or Fehlings solution
Give the conditions needed to form a carboxylic acid from an aldehyde
3
Heat
Reflux
H+ so needs H2SO4
Name the type of reaction to form a carboxylic acid from an aldehyde
Oxidation
Give the reagent needed to form an ester from a carboxylic acid
Alcohol
Give the conditions needed to form an ester from a carboxylic acid
Conc H2SO4
Name the type of reaction to form an ester from a carboxylic acid
Esterification
Give the reagent needed to form a carboxylic acid from an ester
2 options
H+ or OH-
so acid eg: H2SO4 or an alcohol
Give the conditions needed to form a carboxylic acid from an ester
Reflux
Name the type of reaction to form a carboxylic acid from an ester
Hydrolysis
Give the reagents needed to form an ester from an alcohol
3
Carboxylic acid or Acyl chloride or Acid anhydride
Give the conditions needed to form an ester from an alcohol
Conc H2SO4
Name the type of reaction to form an ester from an alcohol
Esterification
Give the reagents needed to form an amide from an acyl chloride
NH3 or 1/2 amine
Name the type of reaction to form an amide from an acyl chloride
nucleophilic substitution
Give the reagents and conditions needed to form an ester from an acid anhydride
Alcohol
H+
Name the type of reaction to form an ester from an acid anhydride
esterification
Give the reagents needed to form a hydroxynitrile from an aldehyde
NaCN(aq) / H+(aq)
name the type of reaction to form a hydroxynitrile from an aldehyde
Nucleophilic addition
Give the reagents and conditions needed to form a carboxylic acid from an acyl chloride
warm water with H+ or OH-
Give the conditions needed to form an acyl chloride from a carboxylic acid
SOCl2
Give the reagent needed to form a carboxylic acid from a nitrile
Acid/ H+(aq)
Name the type of reaction to form a carboxylic acid from a nitrile
Acid hydrolysis
Give the reagent needed to form cyclohexane from benzene
H2
Give the conditions needed to form cyclohexane from benzene
Nickel catalyst
150*C
Name the reaction to form cyclohexane from benzene
Reduction
give the reagents needed to form nitrobenzene from benzene
conc HNO3
conc H2SO4
give the conditions needed to form nitrobenzene from benzene
50*C
Name the reaction to form nitrobenzene from benzene
Electrophilic substitution
nitration
Give the reagents and conditions needed to form phenylamine from nitrobenzene
NaOH
conc H2SO4
Sn catalyst
Name the type of reaction to form pheylamine from nitrobenzene
Reduction
Give the reagent needed to form N-phenylethanamide from phenylamine
Ethanoyl Chloride
Name the type of reaction to form N-phenylethanamide from phenylamine
Acylation
Give the reagents and conditions needed to form phenylethene from benzene
CH3CH2O
AlCl3 catalyst
Name the type of reaction to form phenylethene from benzene
Electrophlic substitution
(friedel-crafts acylation)
then catalytic dehydrogenation
Give the conditions needed to form polystyrene from phenylethene
Ziegler catalyst
Name the reaction to form polystyrene from phenylethene
Polymerisation
Give the reagents and conditions needed to form methylpheylketone from benzene
HCOCl
AlCl3 catalyst
40*C
Name the type of reaction to form methylphenylketone from benzene
Electrophilic substitution (friedel-crafts acylation)
Give the reagents and conditions to form methylbenzene from benzene
RCl
AlCl3 catalyst
40*C
Name the reaction to form methylbenzene from benzene
Electrophilic substitution (friedel-crafts alkylation)