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Organic Chemistry > Aldehyde, Ketones and Carboxylic acid > Flashcards

Aldehyde, Ketones and Carboxylic acid Flashcards

1
Q

1.Strong O.A.
KMnO₄/ H⁺
K₂Cr₂O₇/ H⁺

2.Mild O.A.
DMSO
PCC
PDC
Jones Reagent
Fenton’s Reagent
Collins/saretts Reagent
CAN
Ex.: Jones reagent acts as strong O.A. in 1° Alcohol

A

DMSO - Dimethyl Sulfoxide
Jones Reagent - CrO₃ + H₂SO₄ in acetone
Fenton’s Reagent - FeSO₄ + H₂O₂
Collins/saretts Reagent - CrO₃ + Py in CH₂Cl₂
CAN - Ceric Ammonium Nitrate (Ce⁴⁺)

1° Alcohol + mild O.A. → Aldehyde

2° Alcohol + mild O.A./Strong O.A. → Ketone

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2
Q

3° Al butoxide

Al isopropoxide

A

Oppenauer Oxidation

R₂CHOH + 3° Al butoxide → R₂C=O

R₂C=O + Al isopropoxide → R₂CHOH

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3
Q

O₃/THF
Zn/H₂O

A

Reductive Ozonolysis

Add O to the = bond

CH₂=CH₂ → HCHO + HCHO

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4
Q

CO + H₂O - Water/syn gas
Co₂(CO)₈

A

Oxo process/ Hydroformylation

R-CH=CH₂→ R-CH₂-CH₂-CHO

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5
Q

Dry distillation
Δ

A

Acid derivative of Ca→ Ketone/Aldehyde + CaCO₃

Refer Notes

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6
Q

Pd / BaSO₄

A

Rosenmund Reduction

R-CO-Cl + H₂ → R-CHO + HCl

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7
Q

SnCl₂ / HCl

A

Stephens Reduction (Non selective - strong R.A.)

R-CN + SnCl₂/HCl → R-CH=NH + H₃O⁺→ RCHO + NH₄Cl

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8
Q

DIBAL-H

DiIsoButylALuminium Hydride

A

Selective Reduction (Weak R.A.)

R-CH=CH-CN + DIBAL-H→ R -CH=CH-CH=NH + H₃O⁺→ R-CH=CH-CHO + NH₃

= bond intact

RCOOR’ + DIBAL-H → RCHO = R’-OH

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9
Q

GR → Carbonyl compounds

A

Refer notes

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10
Q

H₂O

A

Gem-di-hal → Carbonyl compounds

refer notes

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11
Q

1.CrO₂Cl₂ + CS₂/CCl₄
2. H₃O⁺

A

Etard rxn

C₆H₅-CH₃ → C₆H₅-CH(OCrOHCl₂)₂ → C₆H₅-CHO

the terminal CH₃ is converted into CHO

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12
Q

CO/CO₂ + dry HCl + anhydr. AlCl₃ + CuCl

A

Gatterman Koch

C₆H₆ → C₆H₅CHO

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13
Q

HCN + HCl + H₂O

A

C₆H₆ → C₆H₅CHO

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14
Q

NaOH + I₂

A

Iodoform rxn

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15
Q

SeO₂
Oxidation

A

EWG-CH₂- → EWG-CO-

CHO-CH₃ → CHO-CHO (Glyoxal)

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16
Q

Zn-Hg
HCl

A

Clemenson’s reduction

RCOR’ → RCH₂R’

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17
Q

NH₂NH₂, KOH
(CH₂OH)₂, Δ

A

Wolff Kishner reduction
RCOR’ → RCH₂R’

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18
Q

HCN + -CO-

A

-C(OH)CN - cyanohydrin

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19
Q

NaHSO₃+ -CO-

A

-C(OH)SO₃Na

All Aldehydes give
Only methyl ketone give (CH₃-CO-R)

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20
Q

RMgX + -CO- + H₃O⁺

A

-C(OH)R

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21
Q

NH₂G + -CO-

A

Refer notes, pH = 3-4

  • Brady’s reagent
  • Schiff’s Base
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22
Q

dil. NaOH / Δ
dil. KOH
dil. Ca(OH)₂, etc

A

Aldol Condensation
- self
- cross
- intermolecular

1.in presence of α-H
2. Forms β-Hydroxy compound and on heating α,β - unsaturated compound

1.Crotonaldehyde
2. Acrolein

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23
Q

Conc. NaOH, KOH, Ca(OH)₂

A

Cannizzaro reaction (redox - disproportionation rxn)
- Self
-Crossed (Methanal always forms acid)
-Intermolecular

  1. Absence of α-H
  2. Only aldehydes
  3. EWG increases rate
  4. Exception:
    - Cl₃CCHO , Ph₃CCHO - no cannizaro
    - (CH₃)₂CHO - gives cannizzaro, not aldol
24
Q

CN⁻

A

Benzoin Condensation

Ph-CHO → Ph-CH(OH)-CO-Ph

formation of Benzoin

25
Q

CH₃COOK

A

Parkin’s Condensation

similar to Aldol, but aromatic aldehyde reacts with aliphatic acid anhydride

26
Q

Tollens Reagent

A

mild OA - Both aromatic and aliphatic aldehydes

NH₄OH + AgNO₃ → [Ag(NH₃)₂]OH or Ag₂O

Rxn : RCHO + Ag₂O → RCOO⁻ + Ag(silver)

27
Q

Fehling’s Reagent

A

mild OA - only aliphatic aldehydes

Fehling A - aq. CuSO₄
Fehling B - Sodium Potassium Tartrate (Rochelle salt)

A + B - CuO
Rxn : RCHO + CuO → RCOO⁻ + Cu₂O (red)

28
Q

Benedict’s Reagent

A

mild OA - only aliphatic aldehydes

Benedict’s solution - Sodium Citrate + Sodium Carbonate + alkaline CuSO₄

  • Gives Brown ppt.
29
Q

Schiff’s reagent

A

mild OA - Both aromatic and aliphatic aldehydes

Schiff’s reagent(colorless) - pararosaniline (pink) + SO₂

Schiff’s reagent + RCHO → Pink appears

30
Q

KMnO₄ + H⁺
K₂Cr₂O₇ + H⁺

A

Strong OA - oxidation of Ketones

RCOR’ → RCOOH + R’CH₂COOH

Pop offs rule - R’ is smaller alkyl group i.e CO stays with smaller alkyl group

31
Q

Peracid
H₂O₂
H₂SO₅
H₂S₂O₈
mCPBA - meta chloroperbenzoic acid

A

Baeyer villiger oxidation
KETONES
RCOR’ →RCOOR’

R’ is bigger alkyl group i.e for unsymmetrical ketone, O is inserted into the bigger alkyl group

e.g. : CH₃COCH₂CH₃ → CH₃COOCH₂CH₃

Refer notes for lactones

ALDEHYDES
RCHO → RCOOH

32
Q

H⁺ / room temp.

A

Polymerisation
refer notes
- para formaldehyde
- meta formaldehyde
- para acetaldehyde (Hypnotic)
- meta acetaldehyde
- mesitylene

33
Q

Dry HCl / H⁺

A

R-CO-R’ + R’‘OH → CR(R’)(OR’‘)OH

CR(R’)(OR’‘)OH + R’‘OH → CR(R’)(OR’’)₂

CH₃CHO + OHCH₂CH₂OH → cyclic acetal

CH₃COCH₃ + OHCH₂CH₂OH → cyclic ketal

34
Q

MgBr / dry ether
H₃O⁺

A

Pinacol - Pinacolone rearrangement

refer notes

Migration power : H > Ph > 3° Alkyl > 2° Alkyl > Alkyl°

35
Q

EAS of Benzaldehyde

A

-CHO : m-directing

Ph-CHO + E⁺ → E-Ph-CHO

E at m-
E⁺ = X⁺ , NO₂⁺, SO₃

note: do not undergo FC rxn

36
Q

RMgX + CO₂
H₃O⁺

A

RMgX + CO₂ → RCOOMgX + H₃O⁺ → RCOOH

37
Q

Mn - acetate / Mn stearate

A

RCH₃ → RCOOH

38
Q

CO + H₃PO₄
H₂O / Δ

A

RCH=CH₂ → RCH₂CH₂COOH

39
Q

Δ

A

Decarboxylation

RCH(COOH)₂ →RCH₂COOH + CO₂

40
Q

RMgX + R’COOH

A

RH + XMgCOOR

41
Q

PCl₃ / PCl₅ / SOCl₂

A

RCOCl

42
Q

RCOOH + R’OH / H⁺

A

RCOOR’

43
Q

RCOOH + [R]

A

RCH₂OH

refer R.A table in Alcohol, Phenol and ether lesson

note: NaBH₄ does not reduce COOH

44
Q

X₂ + Red P

A

Hell Volhard Zelinsky (HVZ) rxn

RCH₂COOH → RCHXCOOH

α - halo acid is formed

45
Q

CaO + NaOH / soda lime
(3:1::NaOH:CaO)

A

Decarboxylation

RCOONa → RH + Na₂CO₃

46
Q

Decarboxylation using Δ

A
  1. Dicarboxylic acid favour decarboxylation

RCH(COOH)₂ → RCH₂COOH

  1. β-Keto acid favour
    decarboxylation

RCOCH₂COOH → RCOCH₃ + CO₂

47
Q

HI / Red P

A

RCOOH → RCH₃

6HI is required for complete reduction i.e +3 to -3

RCH₂OH + 2HI / red P → RCH₃ (-1 to -2)

RCOR’+ 4HI / red P → RCH₃ (+2 to -2)

48
Q

P₂O₅ / Δ

A

formation of anhydride

2RCOOH → RCOOCOR

Phthalic acid → Phthalic anhydride

49
Q

RCOOH + NH₃ / Δ

A

RCOONH₂

50
Q

Rate Of nucleophilic substitution

A

Acid Chlorides > A. anhydride > Ester > Amides

51
Q

PdCl₂ + CuCl₂ in air

A

Wacker’s process

CH₃CH=CH₂ +PdCl₂+H₂O → CH₃COCH₃ + Pd + 2HCI

52
Q

H⁺

A

Beckmann Rearrangement

RR’C=NOH (ketoxime)→ RCONHR + R’CONHR
(N - substituted amine)
It is found that the migrating group is always anti (i.e., trans) to the hydroxyl group. stereospecific.

53
Q

Benzil + NaOH

A

Ph-CO-CO-Ph (benzil) → Ph-C(Ph)(COONa)-OH

54
Q

C₂H₅ONa / H⁺

A

Claisen ester condensation

2CH₃COOC₂H₅

55
Q

3CH₃COCH₃ + dry HCl / Δ

A

Phoron

(CH₃)₂C=CHCOCH=C(CH₃)₂

Organic Chemistry (5 decks)

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