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Summary - Unit 17 - Organic Chemistry II
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ORGANIC CHEMISTRY ItOPTICAL
ISOMERS
↳ form of stereoisomerism I
formula, different arrangement
"
some structural in space
mirror images
↳ have a chiral carbon
↳ carbon atom
4 different groups attached to a
↳ the groups can be arranged in
z wo different
ways which farms two different molecules-enactioners
↳ mirror images of each other that are
·
non-superimposable I will not overlap
↑
i
draw the U
I
I
"
nooch
PLANE POLARISED LIGHT OPTICAL ACTIVITY & REACTION MECHANISMS
-optically active isomers plane polaised light with
this method of
will rotate
Molecules planar profiles can male racenic products
detecting optically
·
an active compound c .
g .
Su1 mechanisms e .
g Su2 mechanisms
.
NOT RACEMIC !
(s-
enationer
One
CH3
↳F
can attack from
Hs--y
I
clockwise , the other
I
-
= either above or
M M
-
commi
%
standard below faming 2
light
,
oscillates in 1 different enactioners
+
-
iX
H !
due to its planar shape
,
-
L
"
Cly Cus .
RACEMATES
there is an even chance
I
zm
-
of each
nucleophile attacking Cus
u single single
a over
y
-
from the bottan/top both reaching in one
u
"
product
Step
↳ rotates place polarised
RACEMIC MIXTURE -
equal amount of each enactioner light differently
C don't rotate place polarised light as
they concer out
So / So
↳ Often achiral substances >
- chiral racemic mixture
racemic mixture
C in a reaction there is on even chance of forming each enantioner
C
difficult and expensive to adapt a reaction to only produce 1 enactioner
- i -
ALDEHYDES AND KETONES
ALDEMUDES US LETONES
POlASSIUM CYANIDE AND CARBONYL GROUPS
-
one
godboiling can'tbeside
mild oxidising
alcohols agent -
points compared to
Dirritant
Cr2017 - Cr
+ acidified -
HCN
~ lab coats gloves TEST
potassium dichromate air ~
D reacts with
- intermolecular forces - to farm toxic goggles V fume cupboards
Glondon forces K2 Cr, 01 potassium + carbony >
- hydroxynitriles or
dipole-dipole cyanide compounds
E
↳ pananent
↳ no O-H suno hydrogen bonding Cra0y" + 14 H +
+ be - -
> 263
+
+ THO B
:soluble in water - 10 silver
↳
dissolved in
dissociates
l + CN-
into -
HCN can also be used
ONLY smaller ones : dissolve
silver coats
it s
but
acid is
laden Reagent
acidic solution
the inside of me
required
larger ones :
have nonpolarhydrocarboning flash
large enough : London forces between non-polar U Me
Mc chairs will be stronger than AgINHz) zaq) + e
-
>
-
Agis) +
INHylag)
:
Y Foc- any
11 Yu
hyorogen banding will not dissolve
H RCO
vi)-n
-
c
-
>
-
-
n - - -
-
c -
a c on
2Ag (NH3)2
-
+
- -
RCHO(aq) 30H -laq) e 2Ag(s) RCO0 (ag) 4NH3 (aq)
-
2420(1)
(
+ + + + +
(ag)
-9
" ↓ " in ii in
REDUCTION :
CU20
Cu2t #
3 fromthe hydroxynitrile
+
Fehling's/Benedict's
reducing agents -
NaBHy dissolved in Methanol
blue >
-
brick
red
solution
no colour
-
change : CN- Snucleophile
[H] and water
Cu2+aa) + e ALDEHUDE-RCUO1ag UCNiaa) H +
(n9) RCH(OH) CN19) +
(aq)
anotwatera
- -
> Cu
+
(s) + + >
- + n
reduce aldehydes/ketones ladnudes UETONE-RCOR"199) + UCN(aq) + M+
(ag) -
> RCRYOn)(Nag) + U
+
lag)
ouced
Ketones- secondary
2 Cring) + RCH0(ag) + SOU-1991 >
- CreO(s) + RCO0- lag) + 34201
alcohols
I
primary)
CARBOXYLIC ACIDS
.
-
coon ... /soluble in water
CARBOXYLIC ACID REACTIONS
the C on the carboxyl group is always C -
hydrogen bond with H20-
weal acids
U nu
--not carbonates CO2 128
DIMERS can fo when ↓ >
- + + salt
O two carboxylic acids hydrogen
-- c
I / bond to each
O over
c
+
a C - -
/x ↑
↑ molecule boing point 2 CHiCOOniag) + NazCO3 (s) >
-
CO2 +
H2O + 2CHsCOONalaq)
U
I I I Ou O
4-
n on u smaller ones. dissolve
have nonpolarhydrocarboning
R-
c -
-
chloro-3-hydroxybutanoic acid larger ones :
position of equilibrium lies left
large enough : London forces between
non-polar
Mc chairs will be stronger than Idissociates poorly-weal acid)
hydrogen banding - will not dissolve
MAKING CARBOXYLIC ACIDS - hydroxides ->
120 + salt
OXIDATION OF HYDROLYSIS OF NITRILES
OR
PRIMARY ALDEHUDES/UETONES
CHycOOniag + NaOn >
-
120 + CH > COONa
44
-
H M G
44 [O] 11
n -
c i- - c -
ou - n -
-
- -
U
in h in hu
0-n
OR
Y
-
↓
-
cen + 2120 +
24 O -
U
ESTERIFICATION
carboxylic reflux di HYDROLYSIS
TERYLENEP
HSOx
alcohols # acids - esters(-coof ester hydrolysis is sped up by acid HC
reflux
sulfuric dilute
acid
BASE HYDROLYSIS NaOHregux
catalyst + socium carbonate
ester hydrolysis is sped up by base
BENZENE-7 ,
4-DICARBOXULI + ETHANE-1 2-DIOL ,
o
using
8
R- - [este
dicarboxylic + did -> > polyester
acid
mu
↳ 120
M U
O -
OIC -
oate perfumesfoodflavouringa eliminated
co
I
I
H
n c c
M solvents
- - -
I compounds dissolve reading in esters
polar
-
other polar
-
- C
-
U low points/evaporate
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