Reactions + Mechanisms chart

ReactionType Reagents Outcome Mechanism

riko
"
Hzoprqesent rt
do mechanism # I 1st

Oxidation(hydrous) Cross,HzQHzSOg 't

os.IS#i*F*::sonamesi .

0€ Nazcrog ,HzQHzSOeRr¥÷Hs
d
" pKa Fraga Hg
← Rtt
Howat
aqueous Cr .
r R
:/ .at h't

)
'll
no.

veryelectrophilic
B
←
typed OH
-

Cr

tomoxygenchtoarge RAH RTE :B

no H2O present OH I / F
T
off!eEagent pay
-

l
Oxidation(Anhydrous) Cros
,E¥¥¥¥ agio
'
E' an:B
ran
H
R R
r
,
"
(a) Anhydrous or
r④←¥¥EE
't
ha
yo ! crew's
"'
(b)
SHEREE
,
Sworn oxidation +

↳1)1€
'
o_O •

I eked x%Mm d

RT"s
C H Ci
, ¥ coz E
oxayfcwon.de HEE're?
, ,

Dmso

-
R
friend a

2) NI
✓
rrs Nkr otsu
GHB
'
"

right
"

-
ri ,
tax

Oxidation WHN (basically 2nd round)

r¥Ha5
°
H2O, acid A
GENERAL MECHANISM P 12 -
WHnt¥-hGb¥ I
A" ""

qq.ogjoen.tt#
:B
't't't
B
r Fa acid

7577k¥43
oH÷÷kqooy
1) PBB not -

s.org#z.3broIEoEIIx
Halides
Alkyl ,

2)
I
inversion

-0
t.sc .
.
-0
'"

PB.rs
Cl
Chalice)
EEE
either Bror
Mechanism
(
-

n →
. sock
- Cl
inversion
mechanism
c. Bl
"Yy )
-

N⑦a,R-NHz etc)
Good nucleophile (
}÷a¥¥
R o least substituted C attacked
IfI
• - •
is
,
,

think type ¥'s ansnenmesnzPREFER leszsobymofsub

Poxide Opening
,

A and 1B
#
nuaeopniieonsnyea inventor protonation

r÷Ei o¥n¥÷→r÷÷
,

1) Basic conditions ¥1753.4999's; 9:29am: In

act as a basel?) .
' "'

" mHz
inversion
protonation
most substituted carbon is attacked
(
•

this q.BA
Weak
nucleophiles (ROH, H2O p÷Eao④-HIt [7%5]
•
2) Acidic Conditions is because
epoxide will
get protonated .
Hzsoa
p
Think of type DIII nudeopn.me#c)o-n Since oxygen does NOT like
being ⑦ charge , aye
-

µ
It

say, chart .
go too and leave
Cregg profile
Pre # much
reacts me
cuz
more electrophilic and therefore

[)££B%
=

more substitution help stabilize

y:B
will
""
the carbon?. "
H outs ab

iii. ← "
aiii
 Chem 215 Reactions + mechanisms

:÷ i ÷ ÷ :÷ f÷ :÷ ÷ ÷
Rxn type Reagents Outcome Mechanism
-

/ qp%Ea.ggded.caritberemovedreyq.io#iifo p?¥i¥
reacts
slowly "

forename 't:#pinioning; 's

0µg pH
, Dharma

Carbonyl Addition
.

XiAtH4E '
That to an
WAIHI : the sown →
¥Bl H
= •
- It

Ishaan
-

2) H3O④ Wolfe
: always
Mami
.

Evora
's

1) Irreversible Nucleophiles
.

incense
-

't
like E- Ezo or THE
countertop
NIT :NaH,kH,LiH
Fiene
&
(only bases)

÷:no¥? ;
-- ?
STRONG d •
Y's base
mi
'
BASE # due issue)
NUCLEOPHILE NOT VERY get * zag
product , 2) H30+wrkuP
Very good nucleophile
•

SOLUBLE @ very FLAMMABLE

OH

* pvim.at#hrYodI&eg)agents.H:canaddfont/back -
stenos forstereocenter.Drzoawh.us#t:eitnerfpJoncsponc Albright :
~¥t
•
aldehydes @ketones actsaonuueophiie
tss
vs%a,

General
n::¥eggin÷*i÷ %i÷
'

mechanism es emanate
ga.sig÷÷÷:p
"

for carbonyl Addition

i :÷
:÷ ÷ ÷ ÷ ÷ : ÷ ÷ ÷ :÷ ÷ ÷ ÷i
:÷÷±÷
÷
j0R~Brt2hi°
#twrkP¥¥qqf
)
"

Carbonyl Addition alcohol (

carbonyl addition a
irreversible .

NBR wi a,

Organolithium reagents n'

"
Li Br
de
I
+ I
-

" "
-

r -
Li .
'

make ufacidbasechem .

-
= it
-

-
=
T
base
any strong

Acetal Formation
o
1, 2roH
→ either
alcohol or thiols
E'sat
products that look like
9¥
AH
Iz jHory
,

1%8%40%3
If
N - 't O

catttzsodstracn.gg HTT R
ro or R R + H2O from E always acidic

Hht MR unstable
↳
(H) Lyra) conditions, a
,

hemiacietallketal
€04
R R always I ¥ocH3 Ho
herniated
pity!
"

unstable ↳a¥E intermediate

"t ) NEVER NEUTRA or
-
ether attach ,

If
Orthioaceta' unstable
-0
REVERSIBLE Nuc OR forward
can go
0 oar backwards
Alcohols @ thiols M
OH
④
QY *oabj¥÷
"
HON 49 OR
I Eoe Mt H2O ④ ← ~
X
assisted
FINAL
Ionization -

(helps push o¥RoH )

 Chem 215 Rxn, Exam I

Reaction Type
Reagents Outcome Mechanism
~H R HOCH 's

goats Bj
fifteen aldehyde ketone
-
to
you go back
Hydrolysis of Acetals Homo# of
•
⑦ *µ
+ →
Had pn^H F D
you Ojetdiolldithiol pay
• ' It
t it ←
backwards rxnfom
-

strong
acid
pin
assisted
formation Acetal
.

Usualyfeater HAB ionization

ff
,¥E÷ →←P¥oH
← H3

Inking : Acetal Ph
Espn f
:B

"÷÷::;rEF↳ pyo
"
unstable
EJ
't assisted
ionization henri acetal

din
%pnIyFNAI
'
X
more favorable

" OH Eioeseeeougntotorm
D HAB
Acetal , another acetal 9 Hz Fernand ⑤ H
f
,

Transaoetylizalionsnongacid
÷÷÷÷
'
"
""

footage cat Hzsoe

is
replace 1 acetal w/ another reason .

Lf
Note : Itis t
likely all off# §¥f
+
can "
get ,
⇐so I tho
protonated but
nothing can
happen By IT * ' ,

wit .
R
'
f Hoyt
R
favorable depvotenate
ring
is
generally .

E FINAL
order of photon /
Addition RXN
0
R i Addition, El
.doesmF¥r
similar to
µeB
depot
11 -
imines :

① HEB
tHzN Rs
~ Y 1- H2O N R
-

tN-04324%1424,n*×µ+
-

a:B
OH OR
tf
,
R R N
-

n
-
N O
→
'

Formation of Imines CH ) fr L L L .

R R ⑦ kHz
NRIsgoodenotg.in)
R R R R
reversible no
•
no acid needed oxime
oxime ether
hydrazone * ⇐ n G
:B IT
,
cuz , ④

TH=HZ° ty
541¥,EiE¥n
Hap
a,
can have ←
small amounts of cat acid aiasxnners
• -

ok a

CEIZstureooemf.hn
-

It
.
,

N
^ bad ( ni
I butno lequw decent
-
-
- -
.

get protonated)
R R R
base @ .

i.
ydrolysisot Imines • addition IEE , ITIL I' ¥99:B
You .
" '
" " '

pitt#3
MEE ✓
LN ←→Mnemi
havingjust Hzoissww .

X H2O
X
antral X

f IE: g+¥soiHsN⑦ g-g-

-
" ' -
Ph

99:B Ph
it
✓
⑦ pit *
=
,NqoH
Has M ←
FT
Ith ph X
-
-

- -

-
assisted
FINAL ionization