precursor to

# Important Common Names - capsaicin.

0 CHO
◦ i 0
och, CHO vanillin
isobutyraldehyde - CHO mesityl oxide O
pthaldehyde OC43
acetone acetophenone bentophenone 0
0 OH
valeraldethe CHECHCHO
# Physical properties acrolein (allyl ald.) cinnamaldehyde-smell of cinnamon
(phenyl acrolein)
- Methanol is a gas while other RCHO are colorless, volatile liquids at room temperature.

- Lower RCHO have pungent smell, higher ones have fruity smell. Ketones have pleasant smell.

- Lower RCHO & Rico are soluble in water since they can form H-bonds w/water, but as size of

-
hydrophobic C- chain increases, the solvation decreases. > ↳ are insoluble in water.

However, they are soluble in organic solvents like ether, benzene, Hells, etc.

- ROH & RCHO are less dense than water.

- BP order: alkane < ethers all/one < alcohol Loic acid ← For one corresponding Hydrocarbon.
carbonyl carbon
- Aldehydes are more reactive than ketones due to: p to
o

i) Inductive effect: More alkyl groups reduce the electrophilicity of the carbonyl carbon. REFER y¼k

i. ENG increases reactivity, EPG decreases it → These gr. are on carbonyl carbon

(Ii) Steric effect: R2 offers more steric hindrance as compared to R.

b/w Cdd ⇒ use DNP rule.
e.g. Compare Reactivity: a. CHSCHO b. CH3 CH3 C. CECH CHO d. NO2-1HZ CHO (Ans: (> do as b)

# Methods of Preparation

⇒ From alcohols
1° 20 3° 1° 2° 3°
① Oxidation: Mild oxidation → at one ✗ Strong oxidation → oil acid one ×

Cut ♂?"I mild oxidising agent that gives alkene Him. rxⁿ) on 3° alcohol.

NBS oxidises 104 2° alcohols to aldehydes and ketones. It can also be used to convert
Br , 0
benzyl compounds to ketones: NBS Br H30
- 2HBr

Gem-dihalides can be hydrolysed to gem-diols which become carbonyl compounds due to instability.

② Dehydrogenation R-CHLOH Ioc ← CHO + HL 7-OH 4%0

③ Oppemaur oxidation °" + ♂ oppemaur
oxidh ♀ + *OH
A
Reagent: i(ProbAL
'MPV Red" a.k.a. A/(comes)3
[Hydride Exchange) R R R R

Reverse process: MPV Reduction - Meerwein-Ponndorf-Verley Reaction

≠
Mech of MPV: 0-C1H 0=24 not 0 OH
O-C "H
bt + +1
LIPROKAL ◦ = Crt LiprokAl ◦ Irv 2. (Prov)ALo=CRL
R R
aldehyde +
alcohol + aldehyde 6 MCTS alcohol

⇒ From acid & acid derivatives

④ Heating Ca salts of Fatty acids:

mixed:
0
e.g. (ROO), Ca: R-I­

- Δ

CA-calo} R-E-R (RCOOLCatCHCO%Ca-a.co, HCHO + RER + HIhaior.

R-4-
I
0
Upon raising the temperature more, the collision free. increases, making intermolecular

products more stable. Hear rxⁿ: HO0H + me COOH mn: 7=150"

- HE03 HCHO + Me!tf, + me Éme
⑤ Thermal decomph of carboxylic acids: CH3 COOH CH3-&-CH, + CO2 + HL0.
coupling → same as above.
⑥ Reduction of Acid Derivatives: R-E- a 4¥ R-E-H

R-E-op'¼,PIBAl-HICK R-& H DIBAL-H-di-isobutyl aluminium hydride

• H30' T=-78°C
④ DIBAL-HI CS2
① H30' #2 R-[I R-CEN DIBAL-H
nexames
R-C
H=NH "30" R-I + NHS ↑
25

Carboxylic acid isn't easily reduced, so it is converted to ROU using SOClz.

Rosenmund Reduction: R-E-a Hd

Bas Of ← Poison R-c"•- H

By using di alkyl cadmium: 2k-l-a + Ried → 2 R-E-R' + each.

⇒ From hydrocarbons:
◦ ↗ HOYA
CS2 HCHO + CH, CHO
⑦ Reductive ozone lysis of alkenes:"
dit. His Dr H °" taut %
. ← Kucherov
⑧ Catalytic Hydration of alkynes: I ↳ sor process
((◦ ((07432
⑨ Oxo process: R-4¥12 +10 + Ha 100°, Pressure R-CH2-CH2-E-H. Anti MIN rule.
Cull
① Wacker's Process: ¥ + PdU2tHnO CH,-&-CH, + Pd +2ha.
Air/Or

⇒ Using Grignard Reagents ,

① From nitrites: HCEN + R-mgI ether # [=NMgI "30" R-CHO + NH3 + mg I

RC=N + R'-MgBr 17am R'-É=NMgBr "30" R'-{=0 + NH3 + mg=%.

① From esters: RE0R + RmgBr " "R-ER + ROH ← Also works for other acid derivatives.

Orthoesth: CHS-Mg Br + (Eto)fH CHCH SEE I mg-957

⇒ Miscellaneous Reactions:
HY OH ◦
130 Using HIOe: It can reduce , I / or °" only. Nothing else.
HO ◦ It HIOT R'CHO + RCHO
R' OH, OH R R: ◦ monk HIO R'COOH + RCOOH.PL/OOCHs)e
can also be used.
+
④ From C-N : R-CH,-NO2 NaOH R-CH = NO, H30" R-CH =O + NOL ↑ Nets Reaction.

R-C EN DIBAL-H R-CH -NH H30" R-CH20 + NH3P

DIBAL-It does not reduce CEC or CEC. #N

/ DIBALH ◦ + NH3

R-CHEN-OH H30" R-CH-O + NHS

aldoxime leg. H30"
150 Hydration/if"%EÑ: R-C- NH tanto R-E-NH2 amide
ex. Hot
R-CEN a- 910

⑥ From alkyl halides w/DMSO: HANI R-CHL-NH2

R-CH =D + Hx + filthy sulphide DMSO on Δ gives
R-CH,-× + 0=5 The nascent oxygen.
dimethyl sulphoxide
Crouch CH0 Other Reagent: A(vg0o3 • 1)
017 Etard Reaction: (ii)2/9 + hr)
H30"-
me (52/1,0"
CHINH, 40 HO CHO + NH4A.
180 Gattermann aldehyde synthesis: + HCN + HU + A 193 O

CHO
190 Galtermann -Koch synthesis: O + co + Hd 1143
H3 Ot
200 Stephen's Reduction: R-CEN.IN#aR-CH=NH R-CH-O + NH3

② Using organolithium or organo cadmium compounds:

R-E-OH + R'Li → R-E-Oli! R-E-R' + LOH

R-Mx + call → Rid + Msd, + MgXz I R2C + R-I-I → RC0R' + Redd-

-
220 Coupling Rx": with NaOH
CH3-E-H dit. Nao't (Hsg, _ H-CH =D
- / -H20 (H3-(H = CH -CH = 0

Steps to solve:(i) Make 2 boomerangs → One w/ carbonyl carbon as center & other w/ α-carbonate.

I/ Remove 140, and join the rest of the compound.

Q.CH,-I-H + CH3-I-CH3 "47 7 to + ¼:c#-Éo - H2O CH}-CH-CH-'Éo

in {1,2C- + it H-CEO - Heo 41%7-at-at-o. + approach.

 precursor to
# Important Common Names - capsaicin.
0 CHO
◦ i 0
och, CHO vanillin
isobutyraldehyde - CHO mesityl oxide O
pthaldehyde OC43
acetone acetophenone bentophenone 0
0 OH
valeraldethe CHECHCHO
# Physical properties acrolein (allyl ald.) cinnamaldehyde-smell of cinnamon
(phenyl acrolein)
- Methanol is a gas while other RCHO are colorless, volatile liquids at room temperature.

- Lower RCHO have pungent smell, higher ones have fruity smell. Ketones have pleasant smell.

- Lower RCHO & Rico are soluble in water since they can form H-bonds w/water, but as size of

-
hydrophobic C- chain increases, the solvation decreases. > ↳ are insoluble in water.

However, they are soluble in organic solvents like ether, benzene, Hells, etc.

- ROH & RCHO are less dense than water.

- BP order: alkane < ethers all/one < alcohol Loic acid ← For one corresponding Hydrocarbon.
carbonyl carbon
- Aldehydes are more reactive than ketones due to: p to
o

i) Inductive effect: More alkyl groups reduce the electrophilicity of the carbonyl carbon. REFER y¼k

i. ENG increases reactivity, EPG decreases it → These gr. are on carbonyl carbon

(Ii) Steric effect: R2 offers more steric hindrance as compared to R.

b/w Cdd ⇒ use DNP rule.
e.g. Compare Reactivity: a. CHSCHO b. CH3 CH3 C. CECH CHO d. NO2-1HZ CHO (Ans: (> do as b)

# Methods of Preparation

⇒ From alcohols
1° 20 3° 1° 2° 3°
① Oxidation: Mild oxidation → at one ✗ Strong oxidation → oil acid one ×

Cut ♂?"I mild oxidising agent that gives alkene Him. rxⁿ) on 3° alcohol.

NBS oxidises 104 2° alcohols to aldehydes and ketones. It can also be used to convert
Br , 0
benzyl compounds to ketones: NBS Br H30
- 2HBr

Gem-dihalides can be hydrolysed to gem-diols which become carbonyl compounds due to instability.

② Dehydrogenation R-CHLOH Ioc ← CHO + HL 7-OH 4%0

③ Oppemaur oxidation °" + ♂ oppemaur
oxidh ♀ + *OH
A
Reagent: i(ProbAL
'MPV Red" a.k.a. A/(comes)3
[Hydride Exchange) R R R R

Reverse process: MPV Reduction - Meerwein-Ponndorf-Verley Reaction

≠
Mech of MPV: 0-C1H 0=24 not 0 OH
O-C "H
bt + +1
LIPROKAL ◦ = Crt LiprokAl ◦ Irv 2. (Prov)ALo=CRL
R R
aldehyde +
alcohol + aldehyde 6 MCTS alcohol

⇒ From acid & acid derivatives

④ Heating Ca salts of Fatty acids:

mixed:
0
e.g. (ROO), Ca: R-I­

- Δ

CA-calo} R-E-R (RCOOLCatCHCO%Ca-a.co, HCHO + RER + HIhaior.

R-4-
I
0
Upon raising the temperature more, the collision free. increases, making intermolecular

products more stable. Hear rxⁿ: HO0H + me COOH mn: 7=150"

- HE03 HCHO + Me!tf, + me Éme
⑤ Thermal decomph of carboxylic acids: CH3 COOH CH3-&-CH, + CO2 + HL0.
coupling → same as above.
⑥ Reduction of Acid Derivatives: R-E- a 4¥ R-E-H

R-E-op'¼,PIBAl-HICK R-& H DIBAL-H-di-isobutyl aluminium hydride

• H30' T=-78°C
④ DIBAL-HI CS2
① H30' #2 R-[I R-CEN DIBAL-H
nexames
R-C
H=NH "30" R-I + NHS ↑
25

Carboxylic acid isn't easily reduced, so it is converted to ROU using SOClz.

Rosenmund Reduction: R-E-a Hd

Bas Of ← Poison R-c"•- H

By using di alkyl cadmium: 2k-l-a + Ried → 2 R-E-R' + each.

⇒ From hydrocarbons:
◦ ↗ HOYA
CS2 HCHO + CH, CHO
⑦ Reductive ozone lysis of alkenes:"
dit. His Dr H °" taut %
. ← Kucherov
⑧ Catalytic Hydration of alkynes: I ↳ sor process
((◦ ((07432
⑨ Oxo process: R-4¥12 +10 + Ha 100°, Pressure R-CH2-CH2-E-H. Anti MIN rule.
Cull
① Wacker's Process: ¥ + PdU2tHnO CH,-&-CH, + Pd +2ha.
Air/Or

⇒ Using Grignard Reagents ,

① From nitrites: HCEN + R-mgI ether # [=NMgI "30" R-CHO + NH3 + mg I

RC=N + R'-MgBr 17am R'-É=NMgBr "30" R'-{=0 + NH3 + mg=%.

① From esters: RE0R + RmgBr " "R-ER + ROH ← Also works for other acid derivatives.

Orthoesth: CHS-Mg Br + (Eto)fH CHCH SEE I mg-957

⇒ Miscellaneous Reactions:
HY OH ◦
130 Using HIOe: It can reduce , I / or °" only. Nothing else.
HO ◦ It HIOT R'CHO + RCHO
R' OH, OH R R: ◦ monk HIO R'COOH + RCOOH.PL/OOCHs)e
can also be used.
+
④ From C-N : R-CH,-NO2 NaOH R-CH = NO, H30" R-CH =O + NOL ↑ Nets Reaction.

R-C EN DIBAL-H R-CH -NH H30" R-CH20 + NH3P

DIBAL-It does not reduce CEC or CEC. #N

/ DIBALH ◦ + NH3

R-CHEN-OH H30" R-CH-O + NHS

aldoxime leg. H30"
150 Hydration/if"%EÑ: R-C- NH tanto R-E-NH2 amide
ex. Hot
R-CEN a- 910

⑥ From alkyl halides w/DMSO: HANI R-CHL-NH2

R-CH =D + Hx + filthy sulphide DMSO on Δ gives
R-CH,-× + 0=5 The nascent oxygen.
dimethyl sulphoxide
Crouch CH0 Other Reagent: A(vg0o3 • 1)
017 Etard Reaction: (ii)2/9 + hr)
H30"-
me (52/1,0"
CHINH, 40 HO CHO + NH4A.
180 Gattermann aldehyde synthesis: + HCN + HU + A 193 O

CHO
190 Galtermann -Koch synthesis: O + co + Hd 1143
H3 Ot
200 Stephen's Reduction: R-CEN.IN#aR-CH=NH R-CH-O + NH3

② Using organolithium or organo cadmium compounds:

R-E-OH + R'Li → R-E-Oli! R-E-R' + LOH

R-Mx + call → Rid + Msd, + MgXz I R2C + R-I-I → RC0R' + Redd-

-
220 Coupling Rx": with NaOH
CH3-E-H dit. Nao't (Hsg, _ H-CH =D
- / -H20 (H3-(H = CH -CH = 0

Steps to solve:(i) Make 2 boomerangs → One w/ carbonyl carbon as center & other w/ α-carbonate.

I/ Remove 140, and join the rest of the compound.

Q.CH,-I-H + CH3-I-CH3 "47 7 to + ¼:c#-Éo - H2O CH}-CH-CH-'Éo

in {1,2C- + it H-CEO - Heo 41%7-at-at-o. + approach.

 precursor to
# Important Common Names - capsaicin.
0 CHO
◦ i 0
och, CHO vanillin
isobutyraldehyde - CHO mesityl oxide O
pthaldehyde OC43
acetone acetophenone bentophenone 0
0 OH
valeraldethe CHECHCHO
# Physical properties acrolein (allyl ald.) cinnamaldehyde-smell of cinnamon
(phenyl acrolein)
- Methanol is a gas while other RCHO are colorless, volatile liquids at room temperature.

- Lower RCHO have pungent smell, higher ones have fruity smell. Ketones have pleasant smell.

- Lower RCHO & Rico are soluble in water since they can form H-bonds w/water, but as size of

-
hydrophobic C- chain increases, the solvation decreases. > ↳ are insoluble in water.

However, they are soluble in organic solvents like ether, benzene, Hells, etc.

- ROH & RCHO are less dense than water.

- BP order: alkane < ethers all/one < alcohol Loic acid ← For one corresponding Hydrocarbon.
carbonyl carbon
- Aldehydes are more reactive than ketones due to: p to
o

i) Inductive effect: More alkyl groups reduce the electrophilicity of the carbonyl carbon. REFER y¼k

i. ENG increases reactivity, EPG decreases it → These gr. are on carbonyl carbon

(Ii) Steric effect: R2 offers more steric hindrance as compared to R.

b/w Cdd ⇒ use DNP rule.
e.g. Compare Reactivity: a. CHSCHO b. CH3 CH3 C. CECH CHO d. NO2-1HZ CHO (Ans: (> do as b)

# Methods of Preparation

⇒ From alcohols
1° 20 3° 1° 2° 3°
① Oxidation: Mild oxidation → at one ✗ Strong oxidation → oil acid one ×

Cut ♂?"I mild oxidising agent that gives alkene Him. rxⁿ) on 3° alcohol.

NBS oxidises 104 2° alcohols to aldehydes and ketones. It can also be used to convert
Br , 0
benzyl compounds to ketones: NBS Br H30
- 2HBr

Gem-dihalides can be hydrolysed to gem-diols which become carbonyl compounds due to instability.

② Dehydrogenation R-CHLOH Ioc ← CHO + HL 7-OH 4%0

③ Oppemaur oxidation °" + ♂ oppemaur
oxidh ♀ + *OH
A
Reagent: i(ProbAL
'MPV Red" a.k.a. A/(comes)3
[Hydride Exchange) R R R R

Reverse process: MPV Reduction - Meerwein-Ponndorf-Verley Reaction

≠
Mech of MPV: 0-C1H 0=24 not 0 OH
O-C "H
bt + +1
LIPROKAL ◦ = Crt LiprokAl ◦ Irv 2. (Prov)ALo=CRL
R R
aldehyde +
alcohol + aldehyde 6 MCTS alcohol

⇒ From acid & acid derivatives

④ Heating Ca salts of Fatty acids:

mixed:
0
e.g. (ROO), Ca: R-I­

- Δ

CA-calo} R-E-R (RCOOLCatCHCO%Ca-a.co, HCHO + RER + HIhaior.

R-4-
I
0
Upon raising the temperature more, the collision free. increases, making intermolecular

products more stable. Hear rxⁿ: HO0H + me COOH mn: 7=150"

- HE03 HCHO + Me!tf, + me Éme
⑤ Thermal decomph of carboxylic acids: CH3 COOH CH3-&-CH, + CO2 + HL0.
coupling → same as above.
⑥ Reduction of Acid Derivatives: R-E- a 4¥ R-E-H

R-E-op'¼,PIBAl-HICK R-& H DIBAL-H-di-isobutyl aluminium hydride

• H30' T=-78°C
④ DIBAL-HI CS2
① H30' #2 R-[I R-CEN DIBAL-H
nexames
R-C
H=NH "30" R-I + NHS ↑
25

Carboxylic acid isn't easily reduced, so it is converted to ROU using SOClz.

Rosenmund Reduction: R-E-a Hd

Bas Of ← Poison R-c"•- H

By using di alkyl cadmium: 2k-l-a + Ried → 2 R-E-R' + each.

⇒ From hydrocarbons:
◦ ↗ HOYA
CS2 HCHO + CH, CHO
⑦ Reductive ozone lysis of alkenes:"
dit. His Dr H °" taut %
. ← Kucherov
⑧ Catalytic Hydration of alkynes: I ↳ sor process
((◦ ((07432
⑨ Oxo process: R-4¥12 +10 + Ha 100°, Pressure R-CH2-CH2-E-H. Anti MIN rule.
Cull
① Wacker's Process: ¥ + PdU2tHnO CH,-&-CH, + Pd +2ha.
Air/Or

⇒ Using Grignard Reagents ,

① From nitrites: HCEN + R-mgI ether # [=NMgI "30" R-CHO + NH3 + mg I

RC=N + R'-MgBr 17am R'-É=NMgBr "30" R'-{=0 + NH3 + mg=%.

① From esters: RE0R + RmgBr " "R-ER + ROH ← Also works for other acid derivatives.

Orthoesth: CHS-Mg Br + (Eto)fH CHCH SEE I mg-957

⇒ Miscellaneous Reactions:
HY OH ◦
130 Using HIOe: It can reduce , I / or °" only. Nothing else.
HO ◦ It HIOT R'CHO + RCHO
R' OH, OH R R: ◦ monk HIO R'COOH + RCOOH.PL/OOCHs)e
can also be used.
+
④ From C-N : R-CH,-NO2 NaOH R-CH = NO, H30" R-CH =O + NOL ↑ Nets Reaction.

R-C EN DIBAL-H R-CH -NH H30" R-CH20 + NH3P

DIBAL-It does not reduce CEC or CEC. #N

/ DIBALH ◦ + NH3

R-CHEN-OH H30" R-CH-O + NHS

aldoxime leg. H30"
150 Hydration/if"%EÑ: R-C- NH tanto R-E-NH2 amide
ex. Hot
R-CEN a- 910

⑥ From alkyl halides w/DMSO: HANI R-CHL-NH2

R-CH =D + Hx + filthy sulphide DMSO on Δ gives
R-CH,-× + 0=5 The nascent oxygen.
dimethyl sulphoxide
Crouch CH0 Other Reagent: A(vg0o3 • 1)
017 Etard Reaction: (ii)2/9 + hr)
H30"-
me (52/1,0"
CHINH, 40 HO CHO + NH4A.
180 Gattermann aldehyde synthesis: + HCN + HU + A 193 O

CHO
190 Galtermann -Koch synthesis: O + co + Hd 1143
H3 Ot
200 Stephen's Reduction: R-CEN.IN#aR-CH=NH R-CH-O + NH3

② Using organolithium or organo cadmium compounds:

R-E-OH + R'Li → R-E-Oli! R-E-R' + LOH

R-Mx + call → Rid + Msd, + MgXz I R2C + R-I-I → RC0R' + Redd-

-
220 Coupling Rx": with NaOH
CH3-E-H dit. Nao't (Hsg, _ H-CH =D
- / -H20 (H3-(H = CH -CH = 0

Steps to solve:(i) Make 2 boomerangs → One w/ carbonyl carbon as center & other w/ α-carbonate.

I/ Remove 140, and join the rest of the compound.

Q.CH,-I-H + CH3-I-CH3 "47 7 to + ¼:c#-Éo - H2O CH}-CH-CH-'Éo

in {1,2C- + it H-CEO - Heo 41%7-at-at-o. + approach.