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Organic Chemistry > Alcohols, Phenols and Ethers > Flashcards

Alcohols, Phenols and Ethers Flashcards

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1
Q

H₃O⁺ / H⁺ + H₂O

A

Acid Hydrolysis - (markovnikov with rearrangement - Carbocation mech.)

R-CH=CH₂ → R-CH(OH)-CH₃

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2
Q
  1. (CH₃COO)₂Hg
  2. NaBH₄/ OH⁻
A

OMDM - oxymercuration demercuration
(markovnikov with no rearrangement)

R-CH=CH₂ → R-CH(OH)-CH₃

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3
Q
  1. B₂H₆/THF
  2. H₂O₂/ OH⁻
A

HBO - hydroboration Oxidation
(Anti-Markovnikov)

R-CH=CH₂ → R-CH₂-CH₂-OH

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4
Q

Reducing Agent

A

Refer the table given in notes

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5
Q

Mg / Dry ether

A

Preparation of GR

R-X + Mg → R-MgX

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6
Q

H₂O

A

Hydrolysis of ester in H⁺ / OH⁻ medium

RCOOR’ → RCOOH + R’OH

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7
Q

aq. NaOH / 623K / 300 atm

A

Dows Process (Benzyne mechanism)

C₆H₅Cl + NaOH → C₆H₅O⁻Na⁺ + H₃O⁺→C₆H₅OH

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8
Q
  1. O₂
  2. H₃O⁺
A

Cumene process (from Cumene Hydroperoxide)

C₆H₅CH(CH₃)₂ + O₂ →C₆H₅C(CH₃)₂OOH + H⁺ → C₆H₅OH + CH₃COCH₃

To note : Cumene → Phenol

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9
Q
  1. H₂S₂O₇ (Oleum)
  2. NaOH / Δ
  3. H₃O⁺
A

From Benzene Sulphonic acid

C₆H₆ + H₂SO₇ → C₆H₅SO₃H + NaOH / Δ → C₆H₅O⁻Na⁺ → C₆H₅OH

To note : C₆H₅SO₃H + NaOH / Δ → C₆H₅O⁻Na⁺

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10
Q
  1. conc. H₂SO₄ + conc. HNO₃ / 60°C
  2. Sn/HCl
  3. NaNO₂ + dil. HCl / 273-278 K
  4. H₂O / Δ (or) dil. H₂SO₄ / 100°C
A

From BDC

C₆H₆ + c.HNO₃+c.H₂SO₄ → C₆H₅NO₂ + Sn/HCl → C₆H₅NH₂ + NaNO₂ + dil. HCl → C₆H₅N₂⁺Cl⁻ →C₆H₅OH

To note:
1. Nitration
2. Reduction
3. Diazotization
4. Hydrolysis

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11
Q
  1. Br₂/Fe
  2. Mg/dry ether
  3. O₂ (excess) / H₃O⁺
A

From GR

C₆H₆ + Br₂/Fe → C₆H₅Br + Mg → C₆H₅MgBr + O₂ + H₃O⁺→ C₆H₅OH

To note:
1. Bromination
2. Prep. of GR
3. GR →Phenol

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12
Q

H₂O₂ / HSO₃F (Fluorosulphuric acid)

A

C₆H₆ + H₂O₂ + HSO₃F → C₆H₅OH

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13
Q

O₂ + V₂O₅ / 315°C

A

C₆H₆ + O₂ + V₂O₅ / 315°C → C₆H₅OH

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14
Q

R-OH + M →
R-OH + MH →
R-OH + MOH →

A

RO⁻M⁺ + H₂
RO⁻M⁺ + H₂
RO⁻M⁺ + H₂O

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15
Q

R-OH + R’MgX

A

R’H + ROMgX

Charge separation and add

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16
Q

Esterification

A

RCOOH + R’OH →RCOOR’ + H₂O

Note :
The Alcohols oxygen stay intact in the ester

one oxygen (O attached to H) from the carboxylic acid is removed as water

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17
Q

PCl₅

A

RCl + POCl₃ + HCl

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18
Q

PCl₃

A

ROH → RCl + H₃PO₃

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19
Q

SOCl₂

A

Darzens process (SN1 - retention)

ROH → RCl + SO₂ + HCl

Both ROH and RCl are either d or l

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20
Q

SOCl₂ + Py (Base)

A

Darzens process (SN2 - inversion)

R-OH → Cl-R + SO₂ + HCl

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21
Q

Conc. H₂SO₄ / 443K

A

Dehydration

ROH → R=R (Alkene)

Carbocation mech. (Rearrangement)

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22
Q

Cu + 573K

A

Dehydrohalogination

α - H elimination
1° ROH → Aldehyde + H₂
2° ROH → Ketone + H₂

β - elimination
3° ROH → Alkene + + H₂O

23
Q

KMnO₄/H⁺
K₂Cr₂O₇/H⁺

A

Strong Oxidising agent

1° ROH + MOA → aldehyde + MOA/SOA →acid

1° ROH + SOA →acid

2° ROH + M/SOA → ketone + SOA/Δ → mixture of acid

3° ROH + M/SOA →Alkene (Dehydration)

24
Q

FeSO₄/H₂O₂
CrO
MnO₂
PCC (Pyridinium chlorochromate)
PDC (pyridinium dichromate)
CAN (Ceric ammonium nitrate)

A

Mild Oxidising agent
(selective oxidation - = bond intact)

1° ROH + MOA → aldehyde + MOA/SOA →acid

1° ROH + SOA →acid

2° ROH + M/SOA → ketone + SOA/Δ → mixture of acid

3° ROH + M/SOA →Alkene (Dehydration)

25
Q

Neutral FeCl₃

A

C₆H₅OH → HCl + (C₆H₅-O-)₃-Fe [Dark violet]

26
Q

CH₃COCl

(CH₃CO)₂O

A

Acetylation

C₆H₅OH → C₆H₅OCOCH₃ (ester)

27
Q

C₆H₅-CO-Cl

Benzoyl chloride

A

Schotten Baumann rxn/Benzoylation

C₆H₅OH +C₆H₅-CO-Cl →C₆H₅-OCO-H₅C₆

28
Q

Zn / Δ

A

C₆H₅OH → C₆H₆

29
Q

Br₂ / H₂O

A

Bromination

C₆H₅OH → 2,4,6-Tribromophenol (white ppt)

30
Q

Br₂ / CS₂

A

C₆H₅OH → HO-C₆H₄-Br (o- and p-)

p- is major

31
Q

c.HNO₃ + c.H₂SO₄

A

C₆H₅OH → Picric acid

32
Q

dil.HNO₃

A

C₆H₅OH →HO-C₆H₄-NO₂ (o- and p-)

o- is major (intramolecular H-bonding)

33
Q

H₂SO₄ + SO₃ / H₂S₂O₇

A

C₆H₅OH →HO-C₆H₄-SO₃H (p-)

only p- is formed as SO₃ is a neutral electrophile

34
Q

Anhydr. AlCl₃

A

no FC rxn

salt formation

35
Q

CHCl₃ + KOH/NaOH

A

Reimer-Teimer rxn

C₆H₅OH →HO-C₆H₄-CHO (o-salicylaldehyde)

36
Q

CCl₄ + KOH/NaOH

A

Reimer-Teimer rxn (Alteration)

C₆H₅OH →HO-C₆H₄-COOH (o-salicylic acid)

37
Q

CO₂ + NaOH

A

Kolbe’s electrolysis

C₆H₅OH →HO-C₆H₄-COOH (o-salicylic acid)

38
Q

Rxn of Salicylic acid

A
  1. Acetylation [CH₃COCl / (CH₃CO)₂O]
    HO-C₆H₄-COOH → aspirin/acetylsalicylic acid

2.Benzoylation [C₆H₅
COCl]
HO-C₆H₄-COOH →Benzoyl salicylic acid

3.1 Esterification [CH₃OH/H⁺]
HO-C₆H₄-COOH →methyl salicylate (oil of wintergreen)

3.2 Esterification [C₆H₅OH/H⁺]
HO-C₆H₄-COOH → Phenyl Salicylate (salol - antiseptic)

39
Q

Na₂Cr₂O₇ / H₂SO₄

or any O.A

A

C₆H₅OH →Benzoquinone (pink)

40
Q

C₆H₅OH + Phthalic anhydride

A

phenolphthalein

41
Q

CH₄ + O₂ + Cu (573K)

A

CH₄ + O₂ + Cu (573K) → CH₃OH

42
Q

Water gas / syngas

CO₂ + 2H₂

A

CO₂ + 2H₂ → CH₃OH

42
Q

Invertase

Zymase

A

C₁₂H₆O₁₁(Sucrose) + H₂O + Invertase → C₆H₁₂O₆(Glucose) + C₆H₁₂O₆(Fructose)

C₆H₁₂O₆(Glucose) + Zymase → C₂H₅OH + CO₂

43
Q

Glycerol + 3HNO₃

A

CH₂(OH)-CH(OH)-CH₂(OH) + 3HNO₃ → Tri Nitro Glycerine

Nitro Glycerine + Kieselguhr → Dynamite

44
Q

conc. H₂SO₄ / 413 K

A

ROH → ROR + H₂O

45
Q

Glycerol + HI (excess)

A

Glycerol + HI (excess) → CH₃-CHI-CH₃

46
Q

ROH + CH₂N₂

A

ROH + CH₂N₂ → CH₃-O-R + N₂

47
Q

RX + NaOR’

A

Williamson ether synthesis (SN2)

RX + NaOR’ → ROR + NaX

If R is less bulky = SN2 and form ether
If R is more bulky = E2 and form alkene
R’ can be bulky

47
Q

RX + Ag₂O

A

RX + Ag₂O → ROR + AgX

48
Q

ROR + [O]

A

Oxidation of ether

ROR + [O]→RO(O)R (peroxy ether)

49
Q

ROR’ + HX

A

Refer notes
SN2 - if 1°, 2°, methyl (Less bulky)
SN1 - if 3°, allyl, benzyl (Stable CC)

50
Q

C₆H₅OCH₃ - anisole

A

o- , p- directing group

note : C₆H₅OCH₂CH₃ - phenetole

51
Q

Epoxides

A

Refer notes

52
Q

Victor Meyer Test

A

1° Alcohol - Red (Blood)
2° Alcohol - Blue
3° Alcohol - Colorless (White)

Hint : RBC

Organic Chemistry (5 decks)

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