ALKOXYMERCURATION
EPOXIDATION
A A
1) Hg(OAc)2/ROH
A
A
H mCPBA
2) NaBH4 B
B RO B
B O
HYDROBORATION
OSMYLATION
A A
A
1) BH3 /THF
A
1) OsO4
OH
OH
2) H2 O2 /HO B 2) NaHSO3 B
B H
SYN B HO
SYN
HYDROGENATION
OZONYLSIS
A A
H2-Pd/C A
A D O D
H 1) O3
EtOH
B
B +
H SYN 2) H2O 2 B O
B OH
BROMINATION
A A A REDUCTION OF ALKYNES
Br2
A
Br + Br
CCl4 B Br H2
B A SYN
Br B
Pd/C -- Lindlar
BROMINATION/NUCLEOPHILIC MEDIA A
Na
ANTI
A A A
NH3
Br2
Br + Br
ROH B RO
B neutral RO B
E1 E 1 Z1
EWG EWG
Z1 HEAT
OXIDATION of ALCOHOLS/REDUCTION of CARBONYLS
R2 Z2 Z3
R1 R2 E3 Z3
Oxidizing Agent E3
O E2 E 2 Z2
[O]
H OH R1 at least one of these there may be more the mirror image is
should be an EDG, than one EWG on also obtained
Reducing Agent to make the rxn go well the dienophile (product is racemic)
[H]
Chemistry Homework Solutions
#59324
Synthesis
Carry iut a FIVE-STEP SYNTHESIS using a reaction from AT LEAST FOUR BOXES, and any other reaction that you know of anything at all, starting from one molecule having SEVEN carbons and one chiral center, and adding anything with FIVE or fewer carbons in each step (YOU WILL MOST LIKELY ADD NO CARBONS IN AT LEAST ONE OF THE STEPS). YOU MUST USE ONE REACTION FROM FOUR OF THE FIVE CATEGORIES OF REACTIONS ON THE SHEET PROVIDED.
There is no difinitive starting material or target product given. It is up to the person doing the problem to make up their own molecules that comply with the above conditions: 7 C's 1 chiral center as a starting material + 5 or fewer C's(reagents) for 5 steps. I have to use any one reaction from 4 of the boxes on the PDF attached.
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- orgsynth.doc
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