SKEMA EXERCISE CARBONYL

SK025 2019/2020 SCHEME CARBONYL

1. 67DRAW STRUCTURES

a.cyclohexanone b. acetophenone d. acetaldehyde e. f. 3,3- g. 3-bromo-2-pentanone h. 2-cyclopentylpropanal
O O ethanal
O dimethylhexanal Br O
CH3 CH O
C CH3 H3C CH3 O H3C CH 3 C H 3 CH CH
CH3 CH CH
O
2. GIVE IUPAC NAME H3C

O CH3 C O O O

C H 3 CH CH b. CH3 O CH3 C CH CH3 CH3 f. O
propanone/acetone cyclopentanone
a. C H 3 c. CH2CH d. CH3 e. C H 3
phenylethanal 3-methyl-2-butanone
2-methylpropanal 3,3-dimethylcyclobutanone

3. SUGGEST CHEMICAL TEST TO DISTINGUISH

a) benzaldehyde from ethanal b) butanone from butanal c) 2-pentanone from 3-pentanone

O CH Fehling Test Tollen Test Iodoform Test

Cu(c2o+mplex) , OH- O [Ag(NH 3)2+ OH-] no reaction O O
CH3CH2C CH3 CH3CH2CH2 C CH3 excess I2 , OH-
+CH3CH2CH2C O- CHI 3

no reaction No silver mirror formed Yellow precipitate formed
O
No brick-red precipitate formed O [Ag(NH 3)2+ OH-] +O Ag no reaction
CH3CH2CH2 CH CH3CH2CH2 C CH3 excess I2 , OH-
CH3CH 2CH 2 C-O-
O No yellow precipitate formed
Cu(c2o+mplex) , OH- Silver mirror formed
+CH3 C O- Cu2O
CH3 CH d) 2-butanol from 3-pentanol
O
Iodoform Test
Brick-red precipitate formed O
HO
H3C CH2 C CH3 excess I2 , OH- +H3C CH2C O- CHI 3
Yellow precipitate formed
no reaction
OH
CH3CH2CHCH2CH3 excess I2 , OH-
No yellow precipitate formed

4. OUTLINE SINTHESIS

a. to produce propanone from propane b. to produce butanone from ethane c. to produce butanal from 1-bromopropane

O O O

CH3 CH 2 CH3 CH3 C CH3 CH3 CH3 CH3 C CH2 CH3 KMnO4 , H+ CH3CH2 CH2 Br CH3CH2 CH2 CH
Br 2 Na 2Cr 2O 7 , H + Mg PCC
uv Br2 CH2CI2
CH3 CH CH3 uv O ether O OH
CH3 CH CH3 OH
Br NaOH (aq) CH3CH2Br Mg CH3CH2MgBr i. CH3 CH OH i. CH2 CH3CH2 CH2 CH2
ether ii. H2O , H+ CH3 CHCH2 CH3 CH3CH2 CH2 MgBr ii. H2O , H+

SK025 2019/2020 SCHEME CARBONYL
d. to produce 2-butanol from butanone
e. to produce butanone from 1-chloropropane

O

CH3 CH2 C CH3 ii.i.LHiA3lOH+4 CH3 CH2 CHCH3 CH3CH2CH2CI CH3 CH2 C CH3
O OH Mg KMnO4 , H+
ether

CH3CH2CH2MgCI
O

i. CH2 H+ OH
ii. H2O , H2O , H+ CH3 CH2 CHCH3

CH3 CH2 CH2CH2OH conc H2SO4 CH3 CH2 CH CH2

SK025 2019/2020 SCHEME CARBONYL

5. REACTIONS OF ALDEHYDE

CH3 CH2 COOH CH3 CH2 CH2OH
D
CH3 CH2 CH2OH C

CH3 CH CH 2 conc H2SO4 A PCC Na 2Cr2O7 , H+ ii.i.LHiA3IOH+4
AA
KMnO 4 , H+ CH2CI2 O CH3 CH 2 CH2OH
i. O3 E
ii. Zn , H 2O
CH3 CH2 CH NaBH 4 ,CH 3OH OH

CH3 CHC2CCOCISpOyrCidI i2neCH3 CH 2BCOOH H2O CH3 CH 2 CH
H2N-OH F OH
O BB NaCN
HCI
+CH3 CH CH 2
M H2NNH 2 CH 3OHN,Ha++HSO3- G CH3 CH2 OH
O CH3 CH2 CH HN CH
OH CN
AICI 3 HO N L NH2 H CH SO3Na
DD CH NO I CH3 CH
CH3 CH2
2 2

i. CH3MgBr
ii. H2O , H+
H2N N NO2 OH

O C CH2CH3 K J OH CH3 CH 2 CH
CH3 CH2 CH
CH3 CH2 CH OCH 3
N NH CH3

NO 2

NO2

SK025 2019/2020 SCHEME CARBONYL

6. REACTIONS OF KETONE OH

OH

OH CH3 CH CH3 CH3 CH CH3
O P
OH
CH3 CH CH3 KMnO 4 , H +Na 2Cr 2O 7 , H + i. LiAIH 4 QCH3 CH CH3
N ii. H 3O +

CH3 C CH3 NaBH 4 ,CH 3OH

O H2O OH

CH3 C CH3 H2N-OH NaCN S CH3 C CH3
HCI
OH
N OH Z H2NNH 2 Na +HSO 3- T OH CH3
HN NH2 OH ,H CH3 C
CH +

3

U OH CN

Y NO 2 CH3 C CH3
CH3 C CH3 SO 3Na
i. CH 3MgBr
H2N N NO 2 ii. H 2O , H +

X W V OH
CH3 C CH3 OH CH3 C CH3

HN N CH3 C CH3 OCH 3
NO 2 CH 3

NO 2

SK025 2019/2020 ALL SCHEME CARBONYL
ALDEHYDE
& KETONE 6.1 CHEMICAL TEST (FILL IN THE BLANK) IODOFORM
EXCESS I2 , OH-
BRADY`S NH2 FEHLING`S SCHIFF TOLLEN O OH

REAGENT Cu2+ complex , OH- NaHSO3 , HCI Ag(NH3)2 +, OH- CH3C @ CH3CH

HN LIGHT YELLOW PRECIPITATE
FORMED
O 2N ALIPHATIC ALL ALL
ALDEHYDE ALDEHYDE ALDEHYDE O
R C CH3
O 2N 2,4-DNPH ONLY
ex cess I2 , OH -
OBSERVATION ORANGE PRECIPITATE FORMED BRICK RED PRECIPITATE FORMED PINKISH PURPLE SILVER MIRROR FORMED
EQUATION O SOLUTION O O
FORMED R CO - + CHI 3

H2N NH R CH R CH
Cu 2+ c o mp lex , O H - [Ag(NH 3)2OH -]
NO 2

O+ NO 2 O O
R CO - + Cu 2O R CO - + Ag
R CH

R CH

N NH

+NO 2 H2O

NO 2

SK025 2019/2020 SCHEME CARBONYL

6.2 CHEMICAL TEST (WRITE EQUATION & OBSERVATION FOR EACH TEST))

COMPOUNDS BRADY`S FEHLING`S SCHIFF TOLLEN IODOFORM

O O PINKISH O O

C H 3 CH 2 CH H 2N NH CH3CH 2 CH PURPLE CH 3CH 2 CH CH3 CH2 C H
NO 2 Cu 2+ complex , OH - [Ag(NH 3)2OH -]
+ SOLUTION
NO 2 FORMED

O ex c es s I2 , OH -
CH 3CH 2 CH

CH 3CH 2 CH O O NO RE A CTION
N NH CH 3 CH 2 CO - + Cu 2O C H3C H2CO - + A g NO LIGHT YELLOW PRECIPITATE IS

+N O 2 H 2O BRICK RED PRECIPITATE IS SILVER MIRROR IS FORMED FORMED
FORMED

NO 2

ORANGE PRECIPITATE IS FORMED

O H 2N NH O O
CH3 CH2 C CH3 NO 2 CH3CH2 C CH3 CH3 CH2 CCH3
O+
O [A g(NH 3)2OH -] exc es s I2 , OH -
CH 3CH 2 CCH 3
NO 2 CH3CH 2 C CH3 NO PINKISH NO RE ACTION
Cu 2+ com ple x , OH - PURPLE NO SILVER MIRROR IS

SOLUTION FORMED

FORMED

O
+CH 3 C H2 C O-
CH 3CH 2 CCH 3 CHI 3
N NH
NO RE ACTION
+N O 2 H 2O

NO BRICK RED PRECIPITATE LIGHT YELLOW PRECIPITATE IS
IS FORMED FORMED

NO 2

ORANGE PRECIPITATE IS FORMED

SK025 2019/2020 SCHEME CARBONYL
O
O CH O CH H 2N NH PINKISH
PURPLE O
NO 2 O CH SOLUTION
CH CH
+ FORMED
NO 2
[Ag(NH 3)2OH-]
exce ss I2 , OH -
CH N NH Cu 2+ complex , OH - O
NO RE A CTION
+N O 2 H 2O NO REA CTION +C O- Ag
NO LIGHT YELLOW PRECIPITATE IS
NO BRICK RED PRECIPITATE SILVER MIRROR IS FORMED FORMED
IS FORMED
NO 2

ORANGE PRECIPITATE IS FORMED

O C CH3 O C CH3 H 2N NH

NO 2 O
C CH3
+ O CCH 3 NO PINKISH O excess I2 , OH-
NO 2 C CH3
PURPLE O
H 3C SOLUTION [Ag(NH 3)2OH -]
C FORMED +C O- CHI 3
NO REACTION
N NH NO SILVER MIRROR IS LIGHT YELLOW PRECIPITATE IS
FORMED
+N O 2 H 2O Cu 2+ complex , OH - FORMED

NO 2 NO REA CTION

ORANGE PRECIPITATE IS FORMED NO BRICK RED PRECIPITATE
IS FORMED

SK025 2019/2020 NO PINKISH SCHEME CARBONYL
PURPLE OO
O
SOLUTION
O H 2N NH O
Cu 2+ complex , OH - FORMED
NO 2

+ [ Ag(NH 3)2OH -] ex ces s I2 , OH -
NO 2
NO REACTION NO RE A CTION
N NH NO RE A CTION NO SILVER MIRROR IS
NO BRICK RED PRECIPITATE NO LIGHT YELLOW PRECIPITATE IS
+N O 2 H 2O FORMED FORMED
IS FORMED

NO 2

ORANGE PRECIPITATE IS FORMED

O O H 2N NH O O O
CH3 CH C H 3C H H 3C CH CH CH3 C H
+ NO 2 Cu 2+ c o mp lex , O H - PINKISH H 3C excess I2 , OH-
OH PURPLE
CH3 CHCH2CH3 H NO 2 [A g(NH 3) 2OH -]
C H3 C SOLUTION
FORMED

N NH O O
CH3CO - + Cu 2O CO - + Ag
+N O 2 H 2O O
H 3C +H CO-
CHI 3

NO 2 BRICK RED PRECIPITATE IS SILVER MIRROR IS FORMED
FORMED
ORANGE PRECIPITATE IS FORMED LIGHT YELLOW PRECIPITATE IS
FORMED
H2N NH HO NO PINKISH HO
OH CH 3CH 2 C HC H3 PURPLE CH3CH2 CH CH3 OH
NO 2 Cu 2+ com ple x , OH -
+C H 3 C H 2 C H C H 3 SOLUTION [A g(NH 3)2OH -] C H3 C H 2CH C H3

FORMED NO RE A CTION e x ces s I2 , O H -
NO SILVER MIRROR IS
NO 2
FORMED
N O R E A C T IO N O

NO ORANGE PRECIPITATE IS FORMED +C H 3 C H 2 C O - CHI 3

NO RE A CTION

NO BRICK RED PRECIPITATE LIGHT YELLOW PRECIPITATE IS
IS FORMED FORMED