SME
Organic Chemistry II
Multistep synthesis
Use this for “Make 3-bromoaniline from benzene. In what order do the three steps go?”
Put in order
Put the steps from benzene to 3-bromoaniline in order.
1
?
2
?
3
?
Assumptions
•
A group already on the ring decides where the next one goes: –NO₂ sends it meta; –NH₂ and –Br send it ortho and para.
•
Brominate while the meta-director is on the ring; reduce last, or the NH₂ sends Br ortho and para.
•
Each step’s product is drawn under it once it is placed, with the new group lit.
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Primary, secondary or tertiary amine?
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Overall yield of a multistep route
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More problem types
Overall yield of a multistep route
Use this for “A four-step route has yields of 92%, 75%, 80% and 64%. What is the overall yield, and how much product do 25 mmol give?”
Atom economy of a reaction
Use this for “Bromoethane (108.97 g/mol) and NaOH (40.00 g/mol) give ethanol (46.07 g/mol) and NaBr. Find the atom economy.”