Summary

Summary UBC CHEM 233 Final Cheat Sheet

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Course
Organic Chemistry

Institution
Organic Chemistry

- UBC CHEM 233 cheat sheet used on the 2022W1 final exam - Comprehensive, includes fischer and newman projections, ARIO, Sn1 and Sn2 reactions, oxidation state, hydrogenation, nucleophilic acyl substitution, carbohydrate cyclization, hydrolysis of enamine, imines and acetals/ketals

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Uploaded on December 25, 2023
Number of pages 1
Written in 2021/2022
Type Summary

organic chemistry
fischer projections
newman projections
ario
sn1
sn2
oxidation state
hydrogenation
nucleophilic acyl sub
carbohydrate cyclization
hydrolysis of enamine
hydrolysis of imines
hydrolysis

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ARIO k[nucleophile][electrophile] polar aprotic

Y
# charge/e-used SN2 : Rate =
Atom : assess which atom bears
ANTI EX ,
-OH GOR

ENisameowOPEXDMSO
acid base rxn .

,
,

Lp strong NU/SB favours SN2 & El 80
Encanstabilizem wl largest
charge +

more SN/ Rate [electrophile] polar protic solvent
Intermediate carbocation solvent
-
radius
: =

:
Resonance () f C or <P more stable It can be stabilized
a
:

Stability 320) SN & El use com. o
.
.

(byresonance resonancandestabilize /charge
El : Rate = k <electrophile I stabilized by
Stereolsomer :E Alkenes
1) charge on same atome look for resonance
Always look at resonance contributors of cons B - Major & resonance
hypercons.
·
.

2
·
Fischer to Induction Stabilize (f) f C by spreading it out
:
Intermediate : carbocation .

(SA)
.

charged atoms
Kielectrophile][base] Antiperiplanar
Look for EN- & ( + )
line bond >
-
disregard size E2 : Rate =

- Lp
atomic radius
& & Good nucleophile : large
The more e-withdrawing groups on cons . 1 > better lon) · base of
-
A (polarizability
> more stabilized 2 Further away EWG is weaker effect Sp3)sp2)Sp same now
SB better Nu
-

.

, :
-

WA O

↑·
more e-
pt
3
SA of
dense EX
KIEOF II better -

che T vs
syn
.

-
.

X00 : No
- Orbital : type of or can affect stability of 2) f. -
Anions more nucleophilic than
The closer e-held to nucleus more stable
molecules
uncharged
,

IP w/ more character more stable for -) charge
↓

-or
Acid-base s orbital smaller than p orbital , bond order
base of IX SN2
↑
as NAH TT
I

T
(R)-2-bromobutane
.

cons -
Alkene(sp2) 44
b)
·

=

Sp3
34
40 Alkane pKa-bo Alkynepkav 25 --
-

I N /- obs -
L
C _
- H Ph -when proton I + - I
1
-

Delocalization
Kea =
Apka CH3 eX
0
OH -
SA
VS .

T
removed
will
,
have .Bharge S -
L -
--
F
->t reactant
on O
.

Need GB to H

,
1 To be delocalized e-must exist
&⑦
product deprotonate substrate analysis Taitsev's rule EX SN/ ?I

-
,
.

unhybridized porbital that can
7 &

accuzon
in ( ++ H
.

overlap wi p orbitals On neighbor atoms
HX -
SNI SN2 El
E2-system provides more
-- 200 ...
.e-must be on sp or sp2 hybridized atom X ~ XX
- I

+
2
H substituted (stable) -
⑦ -
-
> To allow resonance some atoms normally
- Sp3 become Sp2 /X X - x v alkene (E2) -S
-a
,

bond attached ,
* If atom airdy has double

atomcantbedelized
-N
glocalized /X
:

any P ~ ~
coming toNash R
on
Y X -

Form the one wh
state of Br on
--20
-
X ~ ~ ~ v more groups &
Start at point pH = PKa 2
. This is where there will be equal
I
1.

a mounts of ionization state present
I Look at solvent-reagent off alkene > -
-
X - C3 O H

-
pKa < put basic pKa( put acidic
Tribustituted best
L-
.
3

[
acidic
protinated -
T30 ~ X ~ ~ ⑦

-
-
Histidine - L
-

sy in In ISN2-
Inversion
↑
jaz I ar X ~ ~ X X
pH =
3 4 O at chiral C
-
·
·
occurs
.

strong nu-favours Sw Ph
basic acidic ·

deprotinated protonated
PBVz solvent

"
a) EX El Du Ph Br Ph B

cha
:

L

:
CHzON
.

S
b) NaOCHy Solvent

S
E2 product

Y
a) HzSOu
EX El
O
-
EX a
13
, ,

C-c bonds all
.

equal H IIII E
Aromaticity
.
:

8 OH OH ↓ I A
length ; ring often doesn't react um
①
D &A &i X & I
gar /
-

- H
chin
-
in 40
-

"M
I >
-
- n
Delocalization : -must be on ⑧ M -
1.

sp/sp2 Orbital & Hav L 1 /
-
E2 Chair conformers
-&-

All Axial H + LG
alk-
on
- v
-Ph Ph
I
- - Hz C

7
O *
I 2 diff C
Resonance can turn sp3 + sp2
-
Twil
acHals
-

H-X solvent ↑L & a
solvent -

XBr
,

0-so
,

You
Po
. Luckel rule : Un + 2 : n is an
2 integer C 1 , Br , /- Bur H3
W
X =

↓
a
3

!
=
carbon ring-n # of e-in i system 1 I / S
-2-
-
H on

-! ↓
=
I NOT F I

/
Y -

X = -
/
56-n
Alkenes M-bond i n c C bond weaker than Co
-oh 14
: =
&

Acid catalyzed mechanism Hydrohalogenation run
&
-
IEX .

CH3OH (solvent) ↳ El Fischer projections
Hy,W Br
-
&
9) H2SOu (cat)
coo I

⑭
-Or EX -
I ,
W

O
.

-
in
H3C

Y-a
[pdu -
40 back Ph

O
- Front
↓/Let
on

Y
Br =
+
n- au / O-CH3 ACT & catalyzed solvation
E HCLIH
C
-
-
- 1

-

I
- - --
1110
&

de
-
EX I pul-
↑ CHyCH > Ol =

Kil
N-a) H2SOn I
# 3
-

-U
+ g- BV
2
SNow
.

- S
,
HE
-o&
-- Chiral · Ch3 CH3
Il
LI Nyx
Du
I &
I /
Ph Pu
-Y
-

- + -Ma +
products Terpene biosynthesis
1 I L -
-

H2SOu(cat) H20
EX
P
- -XOCH3 a) ,

Look for 5 carbon units
EX
I 4H &
products/QXON OM -
X I branched
.

H
I ·I
CHzOW OX unbroken w/
-

a) H2SOn
.

o -
Mon
-

11 #
Extine-
-S M
k
↳ T
-& i W
I
,
/
In carbon
#
.
2 .
3
...-S I
H I O
& lo
-

&a 10 O
2:0
H
-10
- -
- -
u o = - .

I &
11 1 = / I -
T
-Y
-

- H - 0- - Acetal Ketal
I H RO
OR
.

"-O
S
-
H Aldehyde OR
Ro
-
&
L
-
+ R OU -
/H R/R =>

Oxidation state : e- goes to most E
Ex. -z Oxidation : gain of e- Nucleophilic acyl substitution 1 . Attack Nu Into #C otbreak =

z Reform Carbonyl I bond

W
L-N
PCC : Cros pyr . , uCl
-

EN-atom

I En
; If atom is same
bonds
ji
1
Of O
25
,

agent :
,

= IC eject a
break homolytically EX C-Cbond
.
⑦
T
Jones' re chromic
/g 1111 La
Less basic than Nu
gets le-from bond T
↳ each
2
atom
-
O &
H2SO4 H20 Cros
acid
n Ya R,
Dav A LG
force + basicity
, ,
,
NUE -
driving
&G aldehyde
-

Hydrogenation 1 : He or D pd/C+ C-C bond .
10 alc
Reactivity of cool derivatives Inductive & resonance effects
O alpd/C H2 Hu no stereochem 10 alsJones' Cool Acid P S 0 mixed
magnitude of of correlates to
,

<Esters (amides

Y
<
=
. ,

pcc/Jones' Ketone
-

↑
+ =
-
C coa chloride anhydrides electrophilicity-less steric bulk
(always ( esterification : acid cat
T
> more reactive
111 : Nally or
NaBHu : can
Fischer &i 2) -
-

Hydrogenation 11 reduce HasOn O
-H20 ↳ Of
Lindlar's
RCHOHE 428) very
: +
/C - I
Ne CectC-C
solven tones Cl①
+ aldehydes
, /-
-
I reactive
is
,
-- Catalyst mines
/ o + 420 0
at
Of
10
o /Po #
,
alkene
o O
-
~ E transisterification-
LI
O ester -
LiAllu reduces everything coon+R-on
z alkene I
I -
:

-
Il
T
-
same side (ECF) C-C polar aprotic solvent stable (unreactive Enolates : used Enolate
- -

om/8-R JR
Nu O O low
of amides

i
Hydrolysis O I as
II 100
-
-

NaBHu + I mine W
TR H M-o-H
almp 120 THIN
R/VR
-

NaBHu + aldehyde/Ketone R O
I
1
W
↑
- -

&N-R 11
⑦
HO ⑦ w
H
,
-
> H & R-
+R
&IN -
Tur ↓
C
-
BHut I t
&
-BU --
+ L

&R RI wi * --
-
G R /
RLR ↓
RSR
H
only add
= H or C
reduceso R= H or C &
amine stays protonated as product electrophile to carbon
atom
LiAlHu + COOL - To % ni i
to R-OU
& Y II OAIHz in wor , we Ion) /electrophic
Aldol : run of nu : lenolate
+ a
Il +
4- ↳--
,
H2
Al-n + - --
No1NV
~
-
Al

&Al
/N
-

AlHu H
Gi
HEAT
+ - /or He o - XO - / -P - -
H
nu can react
we itself
laldehyde/ketone)
In
⑦ ↳ 48 /L
-
10-4 v E
-
that denyde
IV man F -N ②
of 0 ⑦ - Sa ①E O +one--tron
H -
ester
LiAIHu H -
+ G + OR zo
von Il /-
A u ↳H-o-M - HO R pro
Allut/orrt
+ T

I I S-
-

I > aldol
in run

Jo
-
A
&P &
an
XM carbonyl gone
Irreversible Heat in aldol run H
-p - V
/
-
R
I mine > elimination Carbohydrate cyclization
3
- -

amide
&
RIN . Neutral mechanism
3 stereoisomers
1Ho
4 //a
+
LiAlly NRz n
Clacid (1) Anhydrides Ealkene *↓C Ou DorOM
&I
mi Typical 2
H
43 AID H
+ &

it9
V :

i
Al Hu / ,
40
-O - NR2 110
-
⑦ I t 40 11
20 Allu +-
n Al-H t &V Y - O /- 2 / + ,

I
+ + --4 H - 3

/
11
NR2 -wrz h S
-NR2 & Tartomers Tollens test aldehydet (t) reducing
:
sugar
for ,
F -

for , or
pla8-a n
40
P phaz-5
Pl Ho -
"
-o Anomers : diastereomers w/
P CHIOH / I /
7.
Hydrolysis of acetals/ketals
-
on R0
-
+
worn a
: -
HO
Stereolsomerism at anomeric
(

7
7

-n
Nuz A ONL no
&
-H
Mr positive no
7
N Keto-end CH2OW
1 .
43CO
"a
E 10 CH3 as H2SOn 420 U20
-
· 4 0 -4 = + 420
,
-

U oon
-
D : Dir
I
10
pra 13-14 open-form b
-

convert
CHO
to pyranose
4004
H
>HO
form
H
/H-Oh
-R
CHO
0 Il
- HOII
-

Un
⑦&- Ej T
ketosts provide (t) test
I
+
-- can CHO
- .

u a R VR /- - u own on OH
4/
ve -pra I
Y ↳
you I

XenoneInd
: -4 won & 11 n 20-22 bottom CHzOU
N 40- on Rotate
R
u
.
H-p-n3 ON
-

--
&
-

2 H RNH - Oh W

en I
--

plag-1 . U
so 04 points
&
-

you
W
I
HaC
- C
I
-

H
O
43
He HO -
City 1 CH2OL D
On H
1
Oh

Int
Ov
S--
O H Hz CO
-S down
iI .
5 0
-

=
-

-
H
&
-

ou & t
I H
V& enamine
no turanose
Or
E On Form

L
- I

=
I on
pla
nin20-27 di
48 -
/
-

+ R For
11 I-OhI I
HO
H fatomer

I n out 3
R mine form turn 48
7 O -
OH
ru p
& into H
of mines CH3
·
Hydrolysis H2N
"Hydrolysis enamine
-
+
of
-

m W

I ital
So h To
#o -
↓
H
-It a H2SOn ,
420 7 . -H
11 +

/ Hij-W #
Last chiral carbon
R or S ?
what
do >
- you see ?
functional
- grp
O II
--

17 N
-IG a H -0-H
In/
u Enamine
Hrs
aldehyde I c= C
H
nin-r-n-RI obondL ↓
Lf
&
.
-

↓ ne -
O
O
-
IV
- i N + 6
24 -H-j-4 Ketonemine L1 11 2 3

15
1
.

Xu
~
- -
R
U
-H
Gl
j H&n N
-H IV
R
R n-do
U
N
1-
M
&0 -Y
Y 2 .
5
n =
↓ %
-

I H
= s
I -
How many atoms Relation between
--M Or
-
& &
9) &

-n
-

H-p-H & Y ring ? OH & -CHOU

gu
--
in
anomeric
34
H
- &- ⑦
jn -
-n
Inor
3
Nu # j Vja
-

Fir
- I
I
↑

voN
&
-

V --
-
I
#
-W
T
.

- 4
u
-n
=

↳
In

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