3.14 organic synthesis

Created by

Heather ward

Cards (40)

How do you get from benzene to nitrobenzene?
Nitration of benzene (electrophillic substitution)

Reagents: concentrated nitric acid in the presence of concentrated sulfuric acid (catalyst)

Conditions: 60 degrees
How do you get from a benzene to a phenyl ketone?
Friedel crafts Acylation (electrophillic substitution)

Reagents: acyl chloride in the presence of anhydrous aluminium chloride catalyst

Conditions: heat under reflux (50 degrees)
How do you get from nitrobenzene to phenyl amine?
Reduction with tin catalyst, HCL, and sodium hydroxide. Heat under reflux.
How do you get from a primary phenyl amine to a secondary phenyl amine?
Nucleophilic substitution with a haloalkane
How do you get from a primary phenyl amine to an n substituted phenyl amide?
Nucleophilic addition elimination with an Acyl chloride.
How do you get from a phenyl ketone to a phenyl hydroxy nitrile?
Nucleophilic addition with NaCN and H2SO4
How do you get from a phenyl hydroxy nitrile to a phenyl nitrile?
Reduction with LiAlH4
How do you get from a phenyl ketone to a secondary phenol?
Reduction with NaBH4
How do you get from a secondary phenol to a phenyl ester?
Esterification with a carboxylic acid, H2SO4 and heat.
How do you get from an alkane to a haloalkane
Reaction - substitution
Mechnism - free radical
Condition - UV or 400 degrees, halogen
How do you get from an alkene to a haloalkane?
Reaction - addition
Mechanism - electrophillic
Condition - aqueous hydrogen halide and room temp
How do you get from an alkene to an alkane?
Reaction - addition
Mechanism - electrophilic
Condition - H2, Ni catalyst, 150 degrees, 5 atms.
How do you get from an Alkene to an alkyl hydrogen sulphate?
Reaction - addition
Mechanism - electrophilic
Conditions - conc H2SO4, room temp.
How do you get from an alkene to an alcohol?
Reaction - addition
Mechanism - electrophilic
Conditions - strong aqueous acid catalyst.
How do you get from a haloalkane to an alkene?
Reaction - elimination
Condition - hot ethanolic sodium hydroxide and reflux
How do you get from a haloalkane to an alcohol?
Reaction - substitution
Mechanism - nucleophilic
Condition - warm aqueous sodium hydroxide and reflux
How do you get from a haloalkane to a nitrile
Reaction - substitution
Mechanism - nucleophilic
Conditions - warm ethanolic potassium cyanide and reflux
How do you get from a haloalkane to a primary, secondary, tertiary amine or quaternary ammonium salt?
Reaction - substitution
Mechanism - nucleophilic
Condition - warm excess ethanolic ammonia in a sealed container
How do you get from an alcohol to an alkene?
Reaction - dehydration
Condition - hot acid catalyst
How do you get from a primary alcohol to an aldehyde?
Reaction - oxidation
Condition - acidified potassium dichromate, heat and distil
How do you get from a primary alcohol to a carboxylic acid?
Reaction - oxidation
Condition - excess acidified potassium dichromate, reflux
How do you get from an aldehyde to a carboxylic acid?
Reaction - oxidation
Condition - acidified potassium dichromate and reflux
How do you get from a secondary alcohol to a ketone?
Reaction - oxidation
Condition - acidified potassium dichromate, heat and distil.
How do you get from a carboxylic acid to an ester?
Reaction - Esterification
Condition - alcohol and H2SO4 catalyst.
How do you get from an alcohol to an ester?
Reaction - Esterification
Condition - carboxylic acid and H2SO4 catalyst
How do you get from an ester to a carboxylic acid?
Acid hydrolysis with dilute acid and reflux or base hydrolysis with alkali, acid, and relfux
How do you get from an Acyl chloride to a carboxylic acid?
Reaction - addition elimination
Mechanism - nucleophilic
Conditions - room temp and water
How do you get from an Acyl chloride to an ester?
Reaction - addition elimination
Mechanism - nucleophilic
Condition - room temp and alcohol
How do you get from an acyl chloride to an amine?
Reaction - addition elimination
Mechanism - nucleophilic
Condition - room temp and 2x ammonia
How do you get from an acyl chloride to an N-substituted amide?
Reaction - addition elimination
Mechanism - nucleophilic
Condition - room temp and 2x amine
How do you get from an acid anhydride to a carboxylic acid?
Reaction - addition elimination
Mechanism - nucleophilic
Condition - room temp and water
How do you get from an acid anhydride to a carboxylic acid and ester?
Reaction - addition elimination
Mechanism - nucleophilic
Condition - room temp and alcohol
How do you get from an acid anhydride to an amine?
Reaction - addition elimination
Mechanism - nucleophilic
Condition - room temp and 2 x ammonia
How do you get from an acid anhydride to an amide?
Reaction - addition elimination
Mechanism - nucleophilic
Condition - room temp and 2 x amine
How do you get from a nitrile to a primary amine?
Reaction - reduction
Condition - either LiAlH4 in ether or H2 and nickel catalyst
How do you get from a primary amine to a secondary amide?
Reaction - addition elimination
Mechanism - nucleophilic
Condition - room temp and Acyl chloride.
write the equation for the formation of the species that reacts with nitrobenzene
HNO3 + H2SO4 = HSO4- + H2O + NO2+
how do you get from an alkene to a polyalkene  
Reaction - addition polymerisation
conditions - pressure and a catalyst
How do you get from an aldehyde/ketone to a hydroxynitrile  
Reaction - addition
mechanism - nucleophilic
conditions - NaCN/HCN and H2SO4
how do you get from a ketone to an alcohol  
reaction - addition / reduction
mechanism - nucleophillic
conditions - NaBH4