racLlce roblems on AddlLlon 8eacLlons Lo Alkenes - Answers

1. uraw Lhe sLrucLure of Lhe producL(s) of each of Lhe followlng reacLlons.

f) 1) Hg(OAc)
2
/ THF, CH
3
CO
2
H
2) NaBD
4
/ NaOD
D
O
O
Mix of Stereoisomers;
see final page
2. ueLermlne Lhe sLrucLure of an lsomer of A (C
10
P
16
) wlLh Lhe followlng chemlcal properLles.
a) Compound A reacLs wlLh P
2
/ d(C) Lo produce cls and Lrans lsomers of 1-lsopropyl-4-
meLhylcyclohexane.
b) 8romlnaLlon of Lhe A produces 1,2,4,3-LeLrabromo-1-lsopropyl-4-meLhylcyclohexane.









3. A cycloalkene wlLh molecular formula C
9
P
16
forms Lhe same Lwo cycloalkyl halldes, shown
below, when elLher reacLlng wlLh P8r or P8r ln Lhe presence of peroxldes. rovlde Lhe sLrucLure
of such alkene.












4. Show an arrow-pushlng mechanlsm for each of Lhe followlng:










3. 1he followlng LransformaLlon occurs Lhrough a radlcal mechanlsm. use Lhe flsh-hook pushlng
mechanlsm Lo follow Lhe LransformaLlon. uraw all resonance sLrucLures for Lhe very sLable
radlcal lnLermedlaLe.










O
CH
3
CH
3
O
O
O
very sLable
O
O








roblem 1 (f)
Cn Lhls parLlcular problem you geL a mlxLure of 4 sLereolsomers, all shown below.





O
O
CH
3
H
3
C
OH
O
2
CCH
3
OH
O
2
CCH
3
OH
H
3
CCO
2
OH
H
3
CCO
2
+ +
+
enantiomers
enantiomers
repared by !ose Laboy