Chapter 9.

0
Carbonyl
Compound
1
Student Learning Time (SLT) Allocation
Slot Lecture Tutorial Practical Total SLT

FTF 1 4 2 7

NFTF 1 4 2 7

Total = 14

2
 Marks Contribution
UPS 3 CHEMISTRY EC025

Topic CLO % Marks Allocated

Carbonyl compound 1 5.6% 3.3/60

PSPM 2 CHEMISTRY EC025

Topic CLO % Marks Allocated

Carbonyl compound 3 8.7% 7.0

3
 Learning Outcomes
Lecture Session:

9.1 Introduction to Carbonyl Compound

a) Draw the general formula of aldehydes and
ketones:

9.2 Nomenclature of Carbonyl Compounds

a) Draw stuctures and name aldehydes and
ketones (parent chain ≤ C10) according to the
IUPAC Nomenclature
 Learning Outcomes
Lecture Session:
9.3 Preparation of Carbonyl Compounds
a) Explain the preparation of carbonyl
compounds through:
i. Ozonolysis of alkene
ii. Oxidation of alcohol
iii. Friedel-Crafts acylation to produce
aromatic ketone
 Learning Outcomes
Lecture Session:
9.4 Chemical Properties of Carbonyl compounds
a) Explain the chemical properties with reference to:
i. Nucleophilic addition with KCN/H+ or NaCN/H+ , water, alcohol, sodium
bisulphite, NaHSO3 and Grignard reagent
ii. Reduction to alcohol using LiAlH4 followed by H3O+ or NaBH4 in methanol or
H2/catalyst
iii. Condensation with ammonia derivatives such as hydroxylamine, hydrazine,
phenylhydrazine and 2,4-dinitrophenylhydrazine (2,4-DNPH) as identification
test for carbonyl compounds.
iv. Oxidation with KMnO4/H+ or Cr2O72- /H+
v. Iodoform test to identify methyl carbonyl group.
 Learning Outcomes
Lecture Session:

9.4 Chemical Properties of Carbonyl compounds

b) Predict the products formed by reactions of carbonyl compounds with
reagents in (a) i, ii, iii, iv and v

c) Explain the identification tests for aldehyde and ketone using:

i. 2,4-dinitrophenylhydrazine
ii. (2,4-DNPH), Tollens’, Fehlings’, and Schiff’s reagent
 Learning Outcomes
Lecture Session:
9.4 Chemical Properties of Carbonyl compounds
d) Differentiate between:
i. Carbonyl and other compounds
ii. Aldehyde and ketone
(Experiment 6: Aldehydes and ketone)

e) Outline the synthesis of compounds related to reactions of carbonyl

compounds
 Introduction to Carbonyl Compound
Ø Functional group: Carbonyl
Ø General formula: CnH2nO
O
C

Class of compound: Aldehyde Class of compound: Ketone

O O
R C H R C R
R = alkyl, aryl or H R and R’ = alkyl or aryl 9
Introduction to Carbonyl Compound
Aldehyde Ketone

O O
R C H R C R
R = alkyl, aryl or H R = alkyl or aryl

10
 Introduction to Carbonyl Compound
Oδ −
C
δ+

Ø Carbonyl compounds are polar molecules due to different electronegativity of atoms bonded
together through the double bond

Ø Since it’s a polar molecule, the attraction force that exist between carbonyl compounds are Van der
waals forces of attraction which is Dipole-dipole interaction and London force.

Ø Carbonyl compounds of aldehyde & ketone tend to undergoes Nucleophilic Addition reaction
on C atom (due to poor electron density region, δ+) 11
 Physical Properties of Carbonyl Compound
Ø For comparative molecular mass, carbonyl compounds have higher boiling point than haloalkanes
and hydrocarbons of (alkanes & alkenes) but lower boiling point than alcohols.

Ø Order of Boiling Point:

Hydrocarbons (alkanes & alkenes) < Haloalkanes < Carbonyl < Alcohol

Ø This is due to the fact that alcohol is a polar molecule in which it can form Hydrogen bond
attraction force between Itself. As we know, hydrogen bond has stronger attraction force than dipole –
dipole interaction and London force. Hence, boiling point of alcohol is the highest compared to the other
compound.
Ø Carbonyl compound is a polar molecule but it can only form Van Der Waals Forces (VDWF) of
attraction of (Dipole-Dipole interaction & London force) between itself.
Ø Carbonyl has higher boiling point than Haloalkanes due to Strength of VDW forces of attraction of
carbonyl is stronger than VDWF of attraction between haloalkanes (Oxygen atom is more
electronegative than Cl or Br atom) 12
 Learning Outcome

9.1 Introduction to Carbonyl Compound

a) Draw the general formula of aldehydes and ketones:

9.2 Nomenclature of Carbonyl Compounds

a) Draw stuctures and name aldehydes and ketones (parent chain ≤ C10)
according to the IUPAC Nomenclature

14
IUPAC Nomenclature of Carbonyl Compound

Structure IUPAC name Common name

O
Methanal Formaldehyde
H–C–H
O
Ethanal Acetaldehyde
CH3–C–H
O
Propanal Propionaldehyde
CH3CH2–C–H
15
IUPAC Nomenclature of Carbonyl Compound

Structure IUPAC name Common name

O
butanal n-butyraldehyde
CH3CH2CH2–C–H
O
CH3(CH2)3–C–H pentanal n-valeraldehyde

O phenylmethanal
C–H ( benzaldehyde )
16
IUPAC Nomenclature of Carbonyl Compound

Structure IUPAC name Common name

O
propanone Acetone
CH3–C–CH3
O
butanone Methyl ethyl ketone
CH3CCH2CH3
O Methyl propyl
2-pentanone
CH3CCH2CH2CH3 ketone

17
IUPAC Nomenclature of Carbonyl Compound
Structure IUPAC name Common name
O
CH3CH2CCH2CH3 3-pentanone Diethyl ketone

O Acetophenone
C–CH3 phenylethanone (phenyl methyl
ketone)

diphenylmethanone
Benzophenone
(diphenyl ketone)
18
18
 Learning Outcomes
Lecture Session:
9.3 Preparation of Carbonyl Compounds
a) Explain the preparation of carbonyl
compounds through:
i. Ozonolysis of alkene
ii. Oxidation of alcohol
iii. Friedel-Crafts acylation to produce
aromatic ketone
 Preparation of Carbonyl Compound
Ozonolysis
of alkene ii) Zn / H2O
5.2 Alkene Alkene Ketone aldehyde

Reactions to Oxidation of 1°
aldehyde

prepare carbonyl 1° & 2 ° alcohol

compound alcohol
8.4 Hydroxy
compound
Ketone
2°
alcohol

Friedel-Craft
acylation
6.3 benzene & Aromatic Ketone
its derivatives 21
 Preparation of Carbonyl Compound

Aldehyde can be prepared by oxidation of primary alcohol using mild oxidizing agent of Pyridinium
ChloroChromate in dicholormethane ( PCC in CH2Cl2 )

General equation:

1° alcohol aldehyde

Example:
1° alcohol aldehyde

22
 Preparation of Carbonyl Compound
Ozonolysis of alkenes produces aldehyde or ketone or both because it depends on the structure of alkenes.

General reaction :
ii) Zn / H2O

Unsymmetrical alkene Ketone aldehyde

Example: H
CH3 H CH3
i) O3
C C C O + O C
CH3 ii) Zn / H2O
CH3 CH3 CH3
Propanone Ethanal

ii) Zn / H2O
23
 Preparation of Carbonyl Compound
Oxidation of 2o alcohols using mild/strong oxidizing agent will yield a ketone.

General equation:

2° alcohol ketone

Example:
O
CH3CH(OH)CH3 CH3—C—CH3
2° alcohol ketone 24
 Preparation of Carbonyl Compound

A good method to prepare aromatic ketones.

Reagent : Acid chloride in the presence of a Lewis acid (FeCl3, FeBr3, AlCl3 , BF3).

General equation:

Benzene Acyl chloride Aromatic Ketone

O
O AlCl3 C—CH3
+ CH3CCl + HCl

Benzene Acyl chloride Aromatic Ketone 25

 Learning Outcomes
Lecture Session:
9.4 Chemical Properties of Carbonyl compounds
a) Explain the chemical properties with reference to:
i. Nucleophilic addition with KCN/H+ or NaCN/H+ , water, alcohol, sodium
bisulphite, NaHSO3 and Grignard reagent
ii. Reduction to alcohol using LiAlH4 followed by H3O+ or NaBH4 in methanol or
H2/catalyst
iii. Condensation with ammonia derivatives such as hydroxylamine, hydrazine,
phenylhydrazine and 2,4-dinitrophenylhydrazine (2,4-DNPH) as identification
test for carbonyl compounds.
iv. Oxidation with KMnO4/H+ or Cr2O72- /H+
v. Iodoform test to identify methyl carbonyl group.
 Learning Outcomes
Lecture Session:

9.4 Chemical Properties of Carbonyl compounds

b) Predict the products formed by reactions of carbonyl compounds with
reagents in (a) i, ii, iii, iv and v

c) Explain the identification tests for aldehyde and ketone using:

i. 2,4-dinitrophenylhydrazine
ii. (2,4-DNPH), Tollens’, Fehlings’, and Schiff’s reagent
 Learning Outcomes
Lecture Session:
9.4 Chemical Properties of Carbonyl compounds
d) Differentiate between:
i. Carbonyl and other compounds
ii. Aldehyde and ketone
(Experiment 6: Aldehydes and ketone)

e) Outline the synthesis of compounds related to reactions of carbonyl

compounds
 Nucleophilic Addition Reaction of Carbonyl
How does the nucleophilic addition reaction occur on carbonyl compound?
δ−
O
C
δ+

Ø From carbonyl structure, we know that the oxygen and carbon that bonded together via
double bond has different electronegativity.

Ø In C=O, the electron density is drawn more towards O atom (due to high
electronegativity), in which making the C atom becomes poor in electron density. This is
what we call as electrophilic site on C atom of Carbonyl 30
 Nucleophilic Addition Reaction
The electron in double bond delocalised
into O atom due to 𝛿 − region of O atom

d-
O O OH
H+
Cd C C
Nu- +

Nu Nu
Nucleophile species attack the
electrophilic site on C atom

Ø When Carbonyl C atom is attacked by a nucleophile, The carbonyl 𝜋 bond is broken and an
intermediate is formed.

Ø The sp! hybrid C atom changed into sp" hybrid C atom

Reminder: This is ONLY for display purpose to show how the nucleophilic addition reaction occurs.
You are NOT required to perform/write the Curly arrows (Mechanism) of this reaction. 31
 Nucleophilic Addition Reaction
Carbonyl undergoes Nucleophilic Addition Reaction with the following reagents:

KCN/H #, NaCN/H #

H2O
O
| Alcohol, R-OH
R—C—R’ Sodium bisulphite, NaHSO3
|
Aldehyde/ketone Grignard Reagent, RMgX
R’ = H or Alkyl
Reduction using NaBH4 or LiAlH4 or H2 / catalyst
32
 Nucleophilic Addition Reaction
General reaction :

O OH
KCN / H+ |
Ø Reagents : Aldehyde or ketone R–C–R’ R–C–R’
R’ = H Or Alkyl |
and
Carbonyl compound CN Cyanohydrin
Ø The HCN is prepared ‘in situ’ by
the reaction of a mixture of KCN O OH
or NaCN with H2SO4. NaCN / H+
H C CH2CH3 H C CH2CH3
Ø Product : Cyanohydrin
Propanal CN Cyanohydrin

O OH
KCN / H+ |
CH3–C–CH3 CH3–C–CH3
|
Propanone CN Cyanohydrin 33
 Nucleophilic Addition Reaction
General reaction :

O OH
Ø Reagents : Aldehyde or ketone H2O / H+ |
and water. R–C–R’ R–C–R’
R’ = H Or Alkyl |
Ø Product : Hydrate (gem-diols) Carbonyl compound OH gem-diol
OH
O
H2O / H+ H C CH2CH3
H C CH2CH3
Propanal
OH
CN gem-diol

O OH
H2O / H+ |
CH3–C–CH3 CH3–C–CH3
|
Propanone OH gem-diol 34
 Nucleophilic Addition Reaction
Ø Aldehyde reacts with alcohol to form hemiacetal
R H3O+
R OH
— O + ROH
C— C
General reaction :
H H OR
Aldehyde Alcohol Hemiacetal

Ø Hemiacetal undergoes further reaction with alcohol to form acetal

R OH R OR
C H3 O+
General reaction : + ROH C
H OR H OR
Hemiacetal Alcohol acetal

Example:
Aldehyde Methanol Hemiacetal Methanol acetal 35
 Nucleophilic Addition Reaction
Ø Ketone reacts with alcohol to form hemiketal
R H3O+
R OH
— O + ROH
C— C
General reaction :
R’ R Hemiketal OR
Ketone Alcohol

Ø Hemiketal undergoes further reaction with alcohol to form ketal

R OH R OR
H3 O+
General reaction : C + ROH C
R OR R OR
Hemiacetal Alcohol acetal

Example:
ketone Methanol Hemiketal Methanol ketal 36
 Nucleophilic Addition Reaction
Ø Reagents : Aldehyde or ketone and O OH
NaHSO3. NaHSO3 |
Ø Product : Bisulphate salt. R–C R–C– SO3-Na+
| |
Ø This reaction is used for purification R’ R’
of aldehyde @ ketone from other Carbonyl compound Bisulphate salt
colourless crystal
non-soluble organic compounds.

37
Nucleophilic Addition Reaction of Carbonyl
H
1° 𝑎𝑙𝑐𝑜ℎ𝑜𝑙
C H methanal H
i O CH3CH2C H + Mg(OH)Br
ii.H3O+
OH
H Ethanal @
aldehyde other H
CH3CH2MgBr i CH3C O than methanal
CH3CH2 C CH3 + Mg(OH)Br
ii.H3O+
Grignard reagents OH
2° 𝑎𝑙𝑐𝑜ℎ𝑜𝑙

CH3 CH3

i CH3C O ketone CH3CH2C CH3 + Mg(OH)Br

ii.H3O+ OH
3° 𝑎𝑙𝑐𝑜ℎ𝑜𝑙
 Reduction Reaction of Carbonyl
Reduction of C=O group

Ø Aldehydes and ketones can be reduced to alcohols using several common reducing
agents
Ø Reduction process: Remove Oxygen and gain Hydrogen atom

Ø Reducing agents :
1. Lithium Aluminium Hydride, LiAlH4 in ether followed by H3O+
2. Sodium BoroHydride, NaBH4 in methanol

3. Catalytic hydrogenation ,H2/Pt or H2/Ni

39
Reduction Reaction of Carbonyl

O OH
NaBH4 in methanol
CH3–C–CH3 CH3CCH3
H

O OH
H2 , Ni
C CH3 C CH3
D
H
40
 Reduction Reaction of Carbonyl
When a compound contains both C=O and C=C, selective reduction of one functional group by proper
choice of reducing agent :
1. LiAlH4 : Does not reduce C=C and C≡C
2. NaBH4 : Does not reduce C=C , C≡C and C=O in acid and esters
3. H2/Pt : Reduce C=C, C≡C and C=O
i.LiAlH4 in ether OH
ii. H3O+ H
Only C=O group is
reduced to alcohol
O NaBH4 in methanol OH
H

Compound contains C=O and C=C

functional group
OH It can reduce both C=C and C=O
H2 , Ni
H 41
 Oxidation Reaction of Carbonyl
Ø Oxidation process means : Gain Oxygen and Loss Hydrogen atom.
Ø Ketones are resistant to oxidation because no hydrogen is attached to the carbonyl carbon atom.

O Carbonyl Carbon atom has no H atom

R C R
Ketone

Ø Aldehydes are easily oxidised to carboxylic acid by using strong oxidising agents because
aldehyde has one Hydrogen atom attached on carbonyl Carbon atom

O Carbonyl Carbon atom has one H atom.

R C H
Aldehyde

Ø Hence oxidation reaction can be used to differentiate between aldehydes and ketones 42
 Oxidation Reaction of Carbonyl
Common oxidizing agents for oxidation reaction with aldehyde:

Type of Oxidising Oxidizing Agent Molecular Observation for positive

agent Formula reaction
§ Purple colour of KMnO4 turn
to colourless.
Hot acidified potassium KMnO4 / H+ ,
permanganate heat § Brown precipitate formed
(MnO2)
Strong Oxidising
agent
Na2Cr2O7 / H+,
Hot acidified chromic heat Orange colour of chromic acid
acid changes to green.
K2Cr2O7 /H+ ,
heat
43
 Oxidation Reaction of Carbonyl
Oxidation of aldehyde
Ø Reactant : Aldehydes.
Ø Reagent : Hot acidified KMnO4, K2Cr2O7, Na2Cr2O7,
Ø Product : Carboxylic acids.
General reaction :
KMnO4 / H+
O ∆ O
|| ||
R—C—H R—C—OH
K2Cr2O7 / H+
Aldehyde Carboxylic acid
Aldehyde can be oxidized due to 1 H ∆
atom bonded on C=O functional group
44
Oxidation Reaction of Carbonyl

45
 Condensation Reaction of Carbonyl with ammonia derivatives
Ø A condensation reaction is a chemical reaction in which two molecules combine to form a larger
molecule with the elimination of a smaller molecule such as water

Condensation with Ammonia Derivatives

Ammonia derivatives are compounds that has substituent (y) in place of one of the hydrogens of
ammonia (NH3).

Generally, the formula of ammonia derivative is: Y-NH2

NO2
H
H-NH2 (Ammonia) NH2-NH2 (hydrazine) |
H—N-N NO2

R-NH2 (10 amine) HO-NH2 (hydroxylamine) 2,4-dinitrophenylhydrazine

46
These are the Ammonia derivatives that you need to memorize
 Condensation Reaction of Carbonyl with ammonia derivatives
General Equation:

elimination reaction occurs at this step

O (eliminate H2O)
H
I addition -H2O C
C H
C=O + Y–N-H
Y-N-H Y-N
Compound
with imine group
(C=N)

47
Condensation Reaction of Carbonyl with ammonia derivatives

This is stage where

elimination reaction occurs
(eliminate H2O)
R R
addition R OH elimination
C=O + NH3 C C=N H + H2O
R N–H
R | R
H
Carbinolamine Imine
‘Unstable intermediate’

48
 Condensation Reaction of Carbonyl with ammonia derivatives
Ø In condensation reaction, NH3 & its derivatives act as nucleophile.
Ø The process involved addition reaction followed by elimination (dehydration)

Ø Condensation with ammonia derivatives can be the Identification Test for the presence of Carbonyl
group, C=O in a compound
Example : carbonyl + ammonia, H2N– H
H H
CH3 – C = O + H2 N –H CH3 – C = N –H + H2O
ethanal ammonia Imine

CH3 CH3
CH3 – C = O + H2 N –H CH3 – C = N –H + H2O
propanone ammonia Imine
49
Condensation Reaction of Carbonyl with ammonia derivatives
Example : Carbonyl + amine, H2N– R

H H
CH3 – C = O + H2 N –CH3 CH3 – C = N –CH3 + H2O
ethanal methylamine Imine

CH3 CH3
CH3 – C = O + H2 N –CH3 CH3 – C = N –CH3 + H2O

propanone methylamine Imine

50
Condensation Reaction of Carbonyl with ammonia derivatives
Example : Carbonyl + Hydroxylamine, H2N – OH

H H
CH3 – C = O + H2 N – OH CH3 – C = N – OH + H2O
ethanal hydroxylamine oxime

CH3 CH3
CH3 – C = O + H2 N – OH CH3 – C = N – OH + H2O

propanone hydroxylamine oxime

51
Condensation Reaction of Carbonyl with ammonia derivatives
Example : Carbonyl + hydrazine

CH3 H H CH3 H
| | | | |
CH3—C O H—N-N — H CH3—C N-N H + H2O

||
||

ketone hydrazine Hydrazone

52
Condensation Reaction of Carbonyl with ammonia derivatives
Example : Carbonyl + phenylhydrazine

CH3 H H CH3 H
| | | | |
CH3—C O H—N-N CH3—C N-N +H2O

||
||

ketone Phenyl hydrazine Phenylhydrazone compound

53
Condensation Reaction of Carbonyl with ammonia derivatives
Example : Carbonyl + 2,4-Dinitrophenylhydrazine

NO2 NO2
CH3 H H CH3 H
| | | | |
CH3—C O + H—N-N NO2 CH3—C N-N NO2 +H2O

||
||

2,4-dinitrophenyl hydrazone compound

2,4-DNPH yellow @ orange
ketone Brady’s reagent precipitate

54
Condensation Reaction of Carbonyl with ammonia derivatives
Summary of Condensation Reaction
NH3 derivatives Name Product Product’s Name
R-NH2 or Ar-NH2 primary amine C=N-R or C=N-Ar Imine
NH2NH2 hydrazine C=NNH2 Hydrazone

NH2-OH hydroxylamine C=N-OH Oxime

NH2NHC6H5 phenyl hydrazine C=NNHC6H5 phenylhydrazone

2,4,dinitrophenylhydrazine C=NNHC6H5(NO2)2 2,4-

C6H3(NO2)2NHNH2
(2,4-DNPH) dinitrophenylhydrazone
55
 Chemical Test of Carbonyl Compounds
Chemical Test of Carbonyl compounds

Brady’s Test Fehling’s Test Tollen’s Test Schiff’s Test Iodoform Test

Ø To detect the To identify

presence of To differentiate aldehyde from ketone methyl carbonyl
carbonyl group, group in
C=O in compound
compound
To differentiate
Ø To differentiate aliphatic
carbonyl compounds
from other
aldehyde from
Hydrocarbon aromatic
compounds aldehyde 56
 Brady’s Test
Ø Purpose of test: to test the presence of carbonyl functional group in compound.

Example : Carbonyl + 2,4-Dinitrophenylhydrazine

CH3 NO2 NO2

+ H H CH3 H
| | | | |
CH3—C O H—N-N NO2 CH3—C N-N NO2
||

||
2,4-DNPH yellow @ orange
Brady’s reagent precipitate

+H2O
Observation:Yellow /orange Precipitate is formed after reaction
Carbonyl (ketone & aldehyde) give positive reaction with Brady’s reagent 57
 Fehling’s Test
Ø Fehling’s reagent will oxidise aldehydes but NOT ketones.
Ø Used to distinguish aliphatic aldehydes from aromatic aldehydes and
ketones.
Ø Reaction with aliphatic aldehydes will produce carboxylate ion and
copper(I) oxide which is brick-red in colour.
Ø In this reaction, copper(II) is reduced to copper(I).
Cu2+ + e à Cu+

58
General equation :
Fehling’s Test
O O
|| ||
R—C—H + Cu2+ + OH- R—C—O- + Cu2O(s)
Blue carboxylate ion Brick-red
precipitate
Example :
CH3C- O- + Cu2O(s)
CH3C- H + Cu2+ + OH- ||
|| Blue O Brick-red
O carboxylate ion precipitate

Observation :
Formation of brick red
59
Fehling solution precipitate with aldehyde.
 Tollen’s Test
Ø Tollen’s reagent: a mixture of aqueous silver nitrate and ammonia. It contains [Ag(NH3)2]+.
Ø Product : Carboxylate ion and Ag mirror.
Ø Also called the silver mirror test.
Ø Aldehyde is oxidised to carboxylate ion.
Ø Ag+ is reduced to Ag (silver)
Ag+ + e- Ag

Ø Observation :
Silver is deposited on the wall of the test tube = silver mirror.

60
General equation :
Tollen’s Test
O O
|| [Ag(NH3)2]+ (aq) ||
R—C—H R—C—O- + Ag
Aldehyde carboxylate ion Silver mirror
Silver mirror
Example :

Propanal propanoate ion Silver mirror

Example :
Benzaldehyde Benzanoate ion Silver mirror
61
Observation : Silver is deposited on the wall of the test tube = silver mirror.
 Schiff’s Test
Ø Purpose: to differentiate aldehyde from ketone
Ø Aldehyde reacts with Schiff’s reagent to give a pinkish purple solution
Ø Ketone gives negative result for Schiff’s test.

Ø No equation of reaction is required for Schiff’s Test

62
 Iodoform’s Test O
||
Ø To detect the presence of methyl carbonyl group.
R — C — CH3
Ø Reagent : Excess I2 in NaOH(aq)
General equation : Methyl carbonyl
group
Observation :
light yellow
precipitate is
formed

Observation :
light yellow
precipitate is
formed 63
 Reduction reaction Oxidation reaction
1° Alcohol i. LiAlH4 in ether KMnO4/H+
formed ii. H3O+ ∆
when aldehyde
Carboxylic acid
is reduced NaBH4 in methanol
(RCOOH)
Na2Cr2O7/H+ Exception for ketone.
2° Alcohol ∆
Ketone cannot be oxidized
formed H2, Pd CrO3/H+ due to no H atom on C=O
when ketone is ∆ functional group
reduced

Condensation reaction
Nucleophilic addition reaction NH3
&
Imine
gem-diol H2O/H+
NH2OH
Aldehyde Ketone oxime
NaHSO3
Bisulphate salt
NH2NH2
Cyanohydrin KCN@NaCN/H+ hydrazone
CH3OH, H3O+ CH3OH, H3O+
acetal/ Hemiacetal/
ketal Hemiketal
phenylhydrazone
i. CH3MgBr
1°, 2° 3° alcohol
ii. H3O+
2,4-nitrophenylhydrazone 65