chem 8a alkene reaction worksheet - chapter 8...chem 8a alkene reaction worksheet - chapter 8...
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Chem 8A Alkene Reaction Worksheet - Chapter 8 Predict the product(s) of the reaction of alkenes 1 through 5 with each of the reagents below. Include relative stereochemistry where appropriate (syn or anti).
1 2 3 4 5 (a) HBr (b) HBr, ROOR (c) Cl2 (d) Cl2, H2O (e) H2, Pd/C (f) 1. BH3, THF; 2. H2O2, NaOH (g)* 1. Hg(OAc)2, THF, H2O; 2. NaBH4 (h) H2O, H2SO4 (cat.) or H3O+ (i) 1. O3; 2. Zn, H2O (or 1. O3; 2. DMS) (j) 1. OsO4; 2. NaHSO3, H2O (or OsO4 catalyst, NMO or cold KMnO4, NaOH) (k) 1. mCPBA (RCO3H); 2. H3O+ 6. Fill in the missing reagents over the arrows
OH
OH
BrO
H
O+
O O
OH
OHOHOH
7. Draw the possible alkene(s) and reagents needed to synthesize the following compounds.
OHBr OHOH
OHO O
(a) (b) (c) (d) (e)
PredictProducts Br Br
y a
p tOH figorh
THE c
y rtd aHale o XPtv 1
OH
HLot
H
fi OH
transit J racemic
JK 1mcPBA OH
OH O
t.sn Enyracemigtrans
racemic
ItBr IIIB a
Eat f f IIb
DI que 47 Clanti stereochem
fl d shenowdoneyffindalkene
at d ye IzzieOH4 y te
DI EatOH
As
ITETE HMi
j 7 aoH
Jkracemic
OH
ata
t
acedracemic
TII
methyl mixturePredictproducts shiftzr I FIBpH
I racemic
r.am z rn sea
anti additionfixture HIT cracemia it1 d p
de or 17KOHpreferstogo tomore substitutedC
it A
gie
j B racemicy 3
KI E
1 581 7 Iacenicracemic
50 5012 5racemic
EI Em1122 gah
ha
oftenon ye
i Into
et
H tan
9EIT j EEEEo'tfk
LETHA at
PredictProductsmixture ofdiastereomers
Br
q if inM Cl 8 mixtureof
fa T diast'sEat
maxi'aIFs 9X Mr d c
H
f S TH If a mixtureof
B re B diast'sI
no longerchiral
OHAH mH A
hito o
OH
A a tons
yk Js l a
hudridthft L dikg't7 tog
mixture of RIS
Draw the possible alkeneG reagentsto make
thorny Br ME ca
re
Ny LETHE net b2HackNaf
or in Eg IO c
Hasty
1HycoFdzHOTHF2 NaBAy
orDMS
OHe
ra E's ne2 NAH503 lot
mCPBA g.LY 1h30