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