ALDEHYDE by KETONE OXIDISEINKMn04.

tt ALDEHYDE / KETONE
→
-
ALCOHOL

STRUCTURES CARBON NUCLEOPHILE

→
aldehyde C- CHO ) → ketone C- co ) -

→
product and mechanism depends on reagent
% É Grignard reagent
-

Ar ,R - -
H Ar ,R - -
Riar ' -
Cyanide
aromatic
-
Organolithium
→ Ar R aliphatic
-

alkynide
- -

,
_

→ carbonyl functional group

8-
:p, carbonyl oxygen 19 ✗ carbon ( alpha )
DGRIGNARD REAGENT
carbon
gjc , carbonyl ,Cy / → 1) R ng ✗
-
-
-

2) 1-130-1
→ product -

Aldehyde SM → 20 alcohol
PHYSICAL PROPERTIES " " "" "

¥""
→
melting point and Boiling point is higher than HC / Ether → mechanism
thisisdue.to dipole dipole interaction of polar carbonyl group g- St

FEAST
-
-

⊕
-
but there are not -

bond between 2 aldehyde / ketone ◦ -

mgx
I
SOMP and BP is still lower than alcohol Mgx R
"
- → ✓
→ can dissolve in water when there are carbon atom
"* .
"
R
- due to carbonyl oxygen forming H -
bond w/ water

↓
REACTIVITY
OH
→
Aldehyde and ketone reactions are mostly nucleophilic 1-1-10 I
+
G ,R
-
→ two factors : steric effect and electronic effect R
-
H
✗
HO Mg
-
-

-
steric effect R
"

L↓ steric effect ,Nu⊖cango into react with carbonyl carbon

easier thus more reactive A CYANIDE
H④
L
aldehyde His smaller than R / Argrovponketonesotreactive → NACNORNZCN /

→ product cyanohydrin inracemix

electronic effect
-

carbon ↑ reactive 0 HO CIN

Lthemoretvewecanget carbonyl NACN
LR , Arisa EDG soit make carbonyl carbon less positive ,
there are
R
'
11
-1-1,12
'

7,7 >/ - H ,R
'
+ Nat
more of this
groupon ketone so ↓ reactive R

→
summary :
reactivity Aldehyde > ketone the nitrile into
→
group can
change
-
amine
- ketone

NUCLEOPHILIC ADDITION -
amide →
carboxylic acid
<
Hydride
L Carbon nucleophiles
Oxygen nucleophiles
L
OXYGEN NUCLEOPHILE →
give acetal / Ketel

overall mechanism
→
1-1-01 OH
H⊕

%
µu%E⊕
E I
enantiomer
.
.

+
RQ " ←
R' f- 1-1,12 R'
→ + '
C- + 1-1
#
N" / ,

"
" ' R +1,12
R
'
R OR
R

HYDRIDE REACTION → reduction reaction to give alcohol

in acidic Jf
condition
→
reagent : 1.) LiAlHyorNaBHu or Hzlpd for catalytic hydrogenation 1-1-01
2) 1-130-1 1012
'

→ product -

aldehyde SM → 1- alcohol
◦

R
/
4-1-1,12
+
HQ .
-

-
ketone SM → 20 alcohol
OR
→ Mechanism ↑

,
' H Li -01
s
⊖
H -
Al H -
I O

r%+*
→
f- HIR
.

↓
OH -0

( %
O -
M

LIOH +
/ 2) 1-130-1 1

GIR
§
/ <
Allott) } Ritt / _ '

R HIR
H ,

→ hidride can
only reduce polar compound so it does not react
with alkene
group
 CARBOHYDRATES
→
types of carbohydrates
NUCLEOPHILIC SUBSTITUTION - Monosac -

Nu
L
Nitrogen -

Oligosac
-

L reaction w/ ✗ -
carbon Poly
- -

monosaccharides
NITROGEN NUCLEOPHILE
→

aldehyde group called Aldose

" "
-
have
→ 10 amine / 2° amine ketone
group called ketose
"
have
product depends on nucleophile
-

-
1- amine
◦ -
imine
amine enamine → Fischer projection ( Dort depend
-
on where -01-1 group is )
-
2 -

" "
- Dextro right-

N R O ' '
left
Levo
-

N - -

1°
d-
¥+1,12 %
11 I
> c- C- +1,12 ,
← H -

y=C → Haworth projection

\ µ , ,z
-
, ,

H ' Anomers
I
-

imine enamine
< the Fischer projections is the same

→ mechanism : addition elimination Lwhenthechain enclose into a ring the -01-1

group of
hemiaceta.IR-0 -

& -0-1-1 can be above or below

a. B- glucose are another

✗ -

CARBON CARBANION
→ formation of a- carbon carbanion
- 0 REACTIONS OF MONOSACCHARIDES
tiff OH

/
C-
c-
I
µ ,R
, →
a-
'
C=c '
/
is

1-1,12
'
¥
/
-

¢+1,12 , GLYCOSIDE FORMATION

→ monosaccharide talc →
glycoside
acidic condition
→
CHZOH
→ the carbanion undergoes CHZOH
EH }
Alkylation
1-4,04
-

Aldol condensation OH CH } -0-1-1 + H2O

+
101-1
-

,
- Crossed Aldol
OH
101-1 OH
glycoside

OXIDATION DISACCHARIDE } POLYSACCHARIDE

-

Aldehy.de/ketonefurthuroxidisetogive-cooH → form glycosidic bong

-

type of this bond determine the carb structure } functn

→ kmn04.tt

OXIDATION
→
reducing sugar canoxidises
→
Aldehyde canoxidise directly
→ ketone need totautomerise.to aldehyde before oxidising

→ Benedict 's Test for reducing sugar