CbD - Organic synthesis Flashcards
What do chemists use synthesis routes for?
To get from one compound to another
Why is it vital that chemists have to be able to make one compound from another?
It is vital for things like designing medicines and making imitation of useful natural substances when the real things are hard to extract.
What do you need to include if you are asked how to make one compound from another in the exam?
1) Any special procedures, such as refluxing.
2) The conditions needed, e.g. high temperature or pressure, or the presence of a catalyst.
3) Any safety precautions, e.g. do it in a fume cupboard.
How do you get from a primary amine to an N-substituted amide? (Reaction conditions)
Acyl chloride
How do you get from an alkane to a bromoalkane? (Reaction conditions)
Br2
UV light
How do you get from a bromoalkane to a primary amine? (Reaction conditions)
NH3/excess ethanoic NH3
Reflux
How do you get from a bromoalkane to a primary alcohol? (Reaction conditions)
NaOH (aq)
Reflux (primary bromoalkanes)
How do you get from a bromoalkane to a secondary alcohol? (Reaction conditions)
NaOH (aq)
Reflux (secondary bromoalkanes)
How do you get from an alkene to a bromoalkane? (Reaction conditions)
HBr
20 degrees
How do you get from an alkene to a dibromoalkane? (Reaction conditions)
Br2
20 degrees
How do you get from an alkene to an alkane? (Reaction conditions)
Ni catalyst
150 degrees
Pressure
How do you get from an alkene to a primary alcohol? (Reaction conditions)
H2SO4 catalyst
Cold H2O
OR
H3PO4 catalyst
Steam
300 degrees
How do you get from a primary alcohol to an alkene? (Reaction conditions)
Conc. H2SO4
170 degrees
Reflux
How do you get from a primary alcohol to an aldehyde? (Reaction conditions)
K2Cr2O7
H2SO4
Heat then distil
How do you get from an aldehyde to a cyanohydrin? (Reaction conditions)
HCN
How do you get from an aldehyde to a carboxylic acid? (Reaction conditions)
K2Cr2O7
H2SO4
Reflux
How do you get from a secondary alcohol to a ketone? (Reaction conditions)
K2Cr2O7
H2SO4
Reflux
How do you get form a ketone to a cyanohydrin? (Reaction conditions)
HCN
How do you get from a primary amide to a carboxylic acid? (Reaction conditions)
H+ (aq)
Heat
How do you get from a carboxylic acid to an ester? (Reaction conditions)
Alcohol
H+ catalyst
Reflux
How do you get from an ester to a carboxylic acid? (Reaction conditions)
H+ (aq)
Reflux
How do you get from an acyl chloride to an ester? (Reaction conditions)
Alcohol
What process makes nitrobenzene from benzene?
Nitration
What process makes chlorobenzene from benzene?
Chlorination
Reaction conditions for nitration
H2SO4
HNO3
55 degrees
Reaction conditions for sulfonation
Fuming H2SO4
40 degrees
Reaction conditions for acylation
RCOCl
AlCl3 catalyst
Reflux
Reaction conditions for chlorination
Cl2
AlCl3 catalyst
Warm
Reaction conditions for alkylation
RCl
AlCl3 catalyst
Reflux
Reaction conditions for turning aminobenzene into benzenediazonium chloride
HNO2/HCl
<5 degrees
Reaction conditions for turning benzenediazonium chloride into a yellow/orange azo compound
Phenol
NaOH (aq)
<5 degrees
Reactions conditions for turning phenol into sodium phenoxide
NaOH
20 degrees
Reactions conditions for turning phenol into phenyl ethanoate
CH3COCl
20 degrees
What sort of process will organic chemists often use when they have to work out how to make a target molecule from existing reagents?
Multi-stage process.
What is retrosynthesis?
A way of planning a synthetic route - starting with the products and working backwards.
What method should you use if you are struggling to find the right steps to get from the reactants to the target product?
Retrosynthesis (start with the products and work backwards).
