Ch.6 (from Alkyl
Rxn Summary
Ch.5
#
Halide
(from Alcohols)
R
-
+
oH
KX
R- OH
R- OH
R
-
-
HORR
R- x,
KOH
x +
SOC12;R-C1
PBrs;R-Br
+
R-X
SO2 HCI
+
R- x
+
So I
HzPO4
can
20Hz0+R
-
R- X
OH
partial
KSH
-
c c
-
+
-
y
R x
+
KCN
Dmso
-xic c
=
X:8
R
-
xNaNs;R
ethanol /water
R
-
x
IT
=
lky)
A
Halide - Alkene
+
-
-
Use
to
-
x
-
1) M50
y
Base
Ant:Rxn
minimize
to OR
& se
W
Bulky
and
S ulforate -> Alkene
O
on
one
X:
⑦
Vox-
H-fetsi
NoH
c
-
=c
L
over
over
SNIISr2
E2
/Bulky Base
E2
Bases for
Oppo-Markornikov
toH
X:0
Sv1, Sr2, El, or ER?
3 EL/EI over SNI
=
Bulky
+
EI/EZ
1SO2
+,0 c
X:0
Rearrangements
& Carbocation
Hz0
10.
~ oH
Nz
2E2
EI/E2
Dehydrohalogenation
H
+
(N +
iR-I+
-
Alcohol - AlkeneEI/EZ
Dehydration
H-c-k-or HsPoyc c
-
Alkyl Iodides
-> Alkenes
x
+R
->
rearrangement
+
X:0
Alkyl Azide: E = NIN-R
2 aitser's Rule & Trans
Elimination
+
↑
SNZ
net inversion & carbocation
D
X:0
(Nitrile)C-C
Ether Inf
H30
R SH
-
ethanol/water
backside attack
simplified
+
Alkyl Cyanide
+
Ch.7 ( to Alkenes
-
acetope/wateR-00R
↑
R'oNYR-OR' R'OH +x.
2R'OH
have
/
- Alcohol
2H
Sa2 has
x
-
Thio
pyridine
Solvolysis
+
-
x:0
+
RCOK
-
R x
OR'
↑
iSulfonate
Halide
-
Ester
>
Alkyl
X:*
0H +
↑
MsCIopTsC;R-Ms(orTs)
OH
-
Ether
Hz0
+
x
+
Alcohol
DMso+R
↑
pyridine
R- OH
R-
R
>
Alcohol Sr1/Sw2
↑
NaOH
-X
R
SNf/Sn2
AIcohol - Alyky1 Halide
Halides)
over
Sn2
Ch. 8
34j -c c-c-Y
↑
X-
(from Alkenes
-c c-
Addition
AIkene - Alkane
Hydrogenation
c
c
=
I
+
(Syn)
H2+M(
H
H
↑
↑
4-
-
-
->
P+, Pd,Ni,
Rh
AIkene - Alykyl Halide
Electrophilic Addition
=c-
HX
i-
CHCls
Alkene - Alcohol
-
>
c
-
c
c=
-
c
+
H
-
-
x
-I
Hydration 20on30
&
HX(Hydrohalogenation)
of
30%
HzSoy
1H 20
0H ->
H
c-c-oH
-
-"
Hydroboration -oxidation (Syn) Oppo-Markovkin
or
1) THE BIts
2) HgOz/0 HO
M
AIkene -
Xz(Anti)
x c
=
BzHo
-
S
XaIHzo
-c c-
j
CH2Is
*
>
68%
#
poxidation
=
-
CH2C2
&
c
~
O
CHzCO2I7
+
Rd0+
+
=
Ozonolysis
- c-c-
or
H28
Xt
(Anti)
↑
--OH will go
for
more
s ubstituted
Ikene-Aldehydes / Ketones / "Carboxylic
&
RooH CPBA
Halohydoi
Alcohol
A
(Syn
↑Peract
-
+
ic c Xzπ -t
-
Alkene-Epoxides
ic
AKene-Alkyl Halide
x
x2
-
=NOH
Halide
Alykyl
now
-
c
=
of
Alkenes
"
i 00 c
1) Os
=
-2) ForKUp"
6
HzOlZn
Acids
or
=
c
YCI)aS
Clearage
of
it
band)
(Alkynes)
Ch.4
Alkyne
-
Bigger AlkyneSN2C-C
NaNHzINHy
-
-
-
X
↑
=
NaNHzINHy
-
. .
-
-
Terminal
-
-
Y
...
X
Alkyl Halide
L
x
-R
RN
x
in
+
Germinal
3 NaNHzINHs
x
-
x
H 20
Alkyoe
Alkane
-
2H2
-
Y
=
"TMC'
Alkyne
--HX
Alkyne
Ikyne
A
Cis Alkene
-
H2
-
I
-
Yor
-
i
=
&
Lindar's
Catalyst
-
=
2 HX
I
2xzj
xx
~
-
xX
c-c
-.
--
-
-
x2
Ikyne, Aldehydes/ Ketones ("Carboxylic
-
Geninal
Trans Alkene Dihalide
Alkyne
**
A
-
-
CiS
&x here
j
-Tetrahaloalkanes
Ozonolysis
HOT
(Syn)
> Ketone/Aldehyde
Hg Cl
-E-
Alkyne
-
Hz SOH
-
(Syn)
Terminal
i Alkyl Halides
-
-
yX-
I
w
....
R-E-R' Internal
-
vincinal
*
x
Alkyne
↑
R'2NaNHz
·
Or
Internal
-
of
1) Os
2)Hz0
Alkynes
Acids
↑
-
RCOH
+
Rort
"
I
.
x
=x
Ch. 10 (Free Radical
AIkane
Alkyl
-
*2
M- H
U or ho
AIkene
(I not
Halide
Br
R-x +Hx
-
picky
very
picky
Halide
JOppo-MarkouniKov Alkyl
↑
HBrg
ROOR
Mir
Peroxide
Alkyne-Trans
R
-
C= 2
-
lylic
A
R
Allylic
-
R
react faster
H
through Allylic
Alkene Halide
+
Dienes)
Carbocations
Prep
-
[YUSTE
+ Hc
A- c1
-
Br
1
T
Conjugated
↓
1)
All
L
Brex
CHzC
Diels-Alder
Conjugated
Dienes
are
preferred
Resonance Forms
ust be available
Halide
↑
*
n
Minor
↑
~
-
j
Kinetic
"1,2-
BR
+
Br
H13M
N
Br
Br
+
NBr
Thermo
"
I,4Y
N'Br
Major
C-C
O
-III
Dienes from Ch.7oxns
Allylic Hydrogens
2)
Both
Diene
j
SN7
must be equivalent
~
#HX
N
benzene
Y
↓
cisdiene dienophile
-
c
R
Carbocations, Radicals, & Avions
Radical
W
W
-
=C
Halides also react faster SN2
212
A
j
NH
Halides
Allylic
1)
H
Na(Li, 12)
(Allylie
Ch.11
Alkere
my
x
Stereo specific
Endo Preferred
k
[Pry)
E
Ch.12
(Areres
&
enzylic Halides react fast than allylichalides
Free Radical Bromination
lkyl
A
Benzene
uses
Carboxylic
↓
NBS
(see
in
SNE/Sr2
Ch. 11)
Acid
Oxidation
X
aacro po
or
10.
*
1
Vinyl
1
Kmn0+1H2018
~
2)H+
a
Po
1
W
Benzenes made from Ch.7rxns
Avene
Non-conjugated Diene
-
Birch Reduction
*
↑xsaqcr6
-
1
alftsIme
out
=>
N
+
j
1
N
I
Isomers
Constitutional
↓
Completely
locations
Stereoisomers
different
it
◦
↓
×
Diastercomers
{H
Switching
Enantiomers
completely changed
Rls to SIR
some
chirality from
Rts to SIR
meso
>
Achiral but
has chiral
centers
Plane of
symmetry
conformational
J
rotation
or
"
cci
"
like
process
Functional Group
Anatom/group
responsible
under
for
in
its
a
reactivity
given set of
a
↑
c-c-alkane
-
-I
c =c
-
-
-C-o-H
-
0
-
a
c
ic c
+)
(R0
(OR)
-
8
avere
I
-
(Benzene
Ring S
-Q
-
alkyl
x
Ketone
R
(FHalosethe
O
aldehyde
-L
H
R
O
P
Carboxylic Acid
- c-0H
&
R-%
R
-
C
OR
O
~
-
0
-c- R
Ester
Anhydride
halide
(haloalkane)
C
-
alkene
=
alcohol
I
-
conditions
alkyne
ether
-
molecule
1
R
-
c
-
x
acylhalide
Rei
Nitro
-Amine