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Organic Reactions Flashcards

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1
Q

Alkane to Halogenoalkane

CH3 CH 3 → CH3 CH2 Cl

A

Limited Cl2 , UV light
Free Radical Substitution

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2
Q

Alkene to Alkane

2HC=CH2 → CH3-CH3

double open open up to add 2 H atoms

A

H2 (g), Ni, heat
Addition of hydrogen, Reduction

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3
Q

Alkene to dihalogenoalkane

2HC=CH2 → CH2Br-CH2Br

double open open up to add 2 Br atoms

A

Br 2 in CCl4 , dark and room temp
Electrophilic Addition
(Orange-red Br 2 in CCl 4 turns colourless)

CCl4 solvent

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4
Q

Alkene to halogenoalcohol

2HC=CH2 → CH2Br-CH2OH

A

Br2 (aq), dark and room temp
Electrophilic Addition
(Orange Br2 (aq) turns colourless)

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5
Q

Alkene to halogenoalkane

2HC=CH2 → CH2H-CH2Br

A

HBr(g), room temp
Electrophilic Addition
(Orange Br2 (aq) turns colourless)

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5
Q

Alkene to alcohol

2HC=CH2 → CH2H-CH2OH

A

Conc. H2SO4 , cold (ii) H2O(l), heat
Electrophilic Addition

Lab Method

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6
Q

Alkene to carboxylic acid

2HC=CH2 → CH2H-COOH

double bond cleaved to give carboxylic acid

A

KMnO4 (aq), H2 SO4 (aq), heat
Oxidation
(purple KMnO 4 turns colourless)

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6
Q

Alkene to diol

2HC=CH2 → CH2OH-CH2OH

A

KMnO4 (aq), H2SO4(aq), COLD
Oxidation
(purple KMnO 4 turns colourless)

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7
Q

Benzene to Cyclohexane

Benzene ring into cyclic ring

A

H2 (g), Ni, high temp and high pressure
Addition of hydrogen, Reduction

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8
Q

Benzene to chlorobenzene

addition of Cl to benzene ring

A

Cl2 , anhydrous AlCl3 , room temp
Electrophilic substitution

AlCl3 is lewis acid catalyst

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8
Q

Benzene to nitrobenzene

addition of NO2 to benzene ring

A

conc HNO3 , conc H2SO4 , heat in water bath at 60degrees
Electrophilic substitution

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9
Q

Benzene to methylbenzene

addition of CH3 to benzene ring

STEP UP REACTION

A

CH3Cl, anhydrous AlCl3 , room temp
Electrophilic substitution

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9
Q

Benzene to phenylethanone

addition of COCH3 to benzene ring

STEP UP REACTION

A

CH3 COCl, anhydrous AlCl3 , room temp Electrophilic substitution
(White fumes of HCl)

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10
Q

benzene to benzoic acid

oxidation of R group on benzene ring

A

KMnO4 (aq), H2 SO4 (aq), heat
Side-chain Oxidation
(purple KMnO 4 turns colourless, white ppt)

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11
Q

Methylbenzene to chloromethylbenzene

substitution of Cl in CH3 of benzene ring

A

Limited Cl2 , UV light / high temperature
Free Radical Substitution

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12
Q

Halogenoalkane to Alcohol

CH3-CH2Br → CH3CH2OH

Don’t forget!!!

A

NaOH(aq) or KOH(aq), heat
Nucleophilic Substitution

OH is the nucleophile

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12
Q

nitrobenzene to phenylamine

replace NO2 with NH2 on benzene ring

IMPTT

A
  1. Sn(s), conc HCl, heat
    2.NaOH(aq), room temp
    Reduction
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12
Q

Halogenoalkane to Ether

CH3-CH2Br → CH3CH2OCH3

STEP UP REACTION

ether is R-O-R’

A

NaOCH3 in methanol, room temp
Nucleophilic Substitution

OCH3 is the nucleophile!!!

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13
Q

Halogenoalkane to Alkene

CH2H-CH2Br → CH2=CH2

IMPTTT

A

NaOH(aq) or KOH(aq) in ethanol, heat
Elimination

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14
Q

Halogenoalkane to Nitrile

CH3-CH2Br → CH3CH2CN

IMPTTT STEP UP REACTION

A

NaCN in ethanol, heat
Nucleophilic Substitution

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15
Q

Halogenoalkane to amine

CH3-CH2Br → CH3CH2NH2

A

NH3 in ethanol, heat in sealed tube
Nucleophilic Substitution
(for polyalkylation use R-Br excess and conc NH3)

polyalkylation product: N(CH3CH2)3

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16
Q

1° Alcohol to Aldehyde

CH3-CH2OH → CH3-COOH

A

K2Cr2O7(aq), H2SO4(aq), heat with immediate distillation
Oxidation
Orange K2Cr2O7 turns green

Cannot use KMnO 4 as aldehyde will oxidise to carboxylic acid

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17
Q

Alcohol to Halogenoalkane

CH3-CH2OH → CH3-CH2Cl

PX5 (where X is CL or Br)

A

Anhydrous PCl5(s), room temp
Nucleophilic Substitution
(produce POCL3 and HCL (white fumes))

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18
Q

Alcohol to Halogenoalkane

CH3-CH2OH → CH3-CH2Cl

PX3 (where X is CL or Br)

A

Anhydrous PCl3(l), room temp
Nucleophilic Substitution
(produce H3PO3)

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19
# Alcohol to Halogenoalkane CH3-CH2**OH** → CH3-CH2**Cl** | SOX2 (where X is CL or Br)
Anhydrous SOCL2(l), room temp Nucleophilic Substitution (produce **SO2** and HCL (white fumes))
20
# Alcohol to Halogenoalkane CH3-CH2**OH** → CH3-CH2**Cl** | dry HX (where X is CL or Br)
dry HCl(g)
21
# Alcohol to Alkene CH3-CH2**OH** → CH2=CH2
**Excess concentrated** H2SO4 , heat or Al2O3 (s), heat Elimination
22
# **2° Alcohol** to Ketone CH3-CHCH3**OH** → CH3-**COOH**
KMnO4 (aq) or Cr2O7 (aq), H2SO4 (aq), heat under reflux Oxidation | Orange K2 Cr2 O 7 turns green. Or purple KMnO 4 turns colourless.
23
# 1° Alcohol to Carboxylic acid CH3-CH2**OH** → CH3-**COOH**
KMnO4 (aq) or Cr2O7 (aq), H2 SO4 (aq), **heat under reflux ** Oxidation (Orange K2Cr2O7 turns green) (purple KMnO 4 turns colourless)
24
# Alcohol to carbon dioxide CH3-CH2**OH** → CO2 + H2O
KMnO4 (aq), H2 SO4 (aq), heat under reflux Oxidation (purple KMnO 4 turns colourless, effervescence, gas evolved forms white ppt with limewater) | Cannot use Cr2 O 7 2− as it is a weaker OA
25
# Aldehyde to Carboxylic acid Aldehyde to Carboxylic acid | Aldehyde (R-COH)
KMnO4 (aq) or Cr2 O7 (aq), H2 SO4 (aq), heat under reflux Oxidation | Orange K2 Cr2 O 7 turns green. Or purple KMnO 4 turns colourless.
25
# Alcohol to Ester Alcohol to Ester | STEP UP RXNNNN
CH3 COOH, conc H2 SO4 , heat or **anhydrous** CH3 COCl, room temp Condensation | Rxn only **reversible** for CH3COOH
26
# Iodoform Test RCHCH3OH → RCOO- + CHI3 | C attached to H, CH3 and OH
I2 (aq), NaOH(aq), heat Oxidation (Decolourisation of brown solution + pale yellow ppt) | Distinguishing test for specific alcohol
27
# Alcohol to Carboxylate ion CH3CH2OH → CH3**COO-Na+** + **½**H2 (g)
Na(s), room temp Redox | Effervescence, gas evolved extinguished lighted splint with ‘pop’ sound
28
# Phenol to Phenoxide + H2 Phenol → Phenoxide + **½**H2(g)
Na(s), room temp Redox | Effervescence, gas evolved extinguished lighted splint with ‘pop’ sound
29
# Phenol to Phenoxide Phenol → Phenoxide + H2O
NaOH(aq), room temp Acid-base | Phenol reactive enough to undergo acid base
30
# Phenol to phenate ester Phenol → benzene attached to **ester** | IMPTTTT
NaOH (aq) followed by anhydrous CH3 COCl, room temp Condensation
31
# Phenol to phenate ester Phenol → Phenol with NO2 at 2 or 4 position
dilute HNO3 (aq), room temp Electrophilic substitution | OH is 2,4-directing, strongly activating hence milder condition
32
Phenol → Phenol tri-sub NO2 at 2,4,6 position
**conc** HNO3 , room temp Electrophilic substitution | -OH is 2,4-directing, strongly activating hence milder condition
33
Phenol → Phenol with Br2 at 2 or 4 position
Br 2 in CCl4 , room temp Electrophilic substitution | -OH is 2,4-directing, strongly activating hence milder condition
34
Phenol → Phenol tri-sub Br2 at 2,4,6 position
Br2 **(aq)**, room temp Electrophilic substitution (Decolourisation of orange Br2 (aq) , formation of **white ppt**) | -OH is 2,4-directing, strongly activating hence milder condition
35
**Phenylamine** → Phenol tri-sub Br2 at 2,4,6 position
Br2 **(aq)**, room temp Electrophilic substitution Decolourisation of orange Br2 (aq) , formation of white ppt | -NH 2 is 2,4-directing, strongly activating hence milder condition
36
# Aldehyde to Cyanohydrin R-COH → R-CHOH**CN** | STEP UP REACTIONNNN IMPTTTTT
HCN, **trace of NaOH**, cold Nucleophilic Addition
37
# Distinguishing test for aldehyde and ketone 2,4-DNPH
2,4-DNPH warm Oxidation yellow ppt formed
38
Distinguishing test for aldehyde
Tollens’ Reagent warm Oxidation Silver mirror (Ag) or grey precipitate formed
39
Distinguishing test for straight aldehyde
Fehling’s Reagent Warm Oxidation Brick red precipitate formed (Cu2 O) | Not strong enough to oxidise **aromatic aldehyde**
40
# Methyl ketone to carboxylate ion + pale yellow ppt R-C=O-CH3 + **3**I2 + **4**OH- → carboxylate ion + **3**I- + **3**H2O | STEP DOWN REACTION
I2 (aq), NaOH(aq), heat Oxidation Decolourisation of brown solution + pale yellow ppt | Distinguishing test for carbonyl with RCOCH3
41
Aldehyde to 1° Alcohol
LiAlH 4 in dry ether, room temp or NaBH 4 in methanol, room temp or H2(g), Ni, heat reduction
42
Ketone to 2° Alcohol
LiAlH 4 in dry ether, room temp or NaBH 4 in methanol, room temp or H2(g), Ni, heat reduction
43
Carboxylic acid to 1° Alcohol
LiAlH 4 in dry ether, room temp reduction | only LiAlH4 can be used
44
# Carboxylic acid to Ester R-COOH → R-**COO**CH3
**CH3OH**, **conc** H2SO4 , heat Condensation
45
Carboxylic acid → carboxylate ion + **½**H2 (g)
Na(s), room temp Redox | Effervescence, gas evolved extinguished lighted splint with ‘pop’ sound
46
# Carboxylic acid to acid chloride R-COOH → R-**COCl**
anhydrous PCl5 (s), or anhydrous SOCl2 (l) Nucleophilic Substitution white fumes of HCl produced | cannot use dry HX
47
# Acid Chloride to Amide R-COCl → R-**NHCO**-R
**R-**NH2 , room temp Condensation (white fumes of HCl) | does not react with tertiary amine
48
# Acid Chloride to Carboxylic acid R-COCl → R-COOH | IMPTTT
H2O(l), room temp Hydrolysis
49
# Ester to two alcohols R-COO-R → R-OH + R-OH
LiAlH 4 in dry ether, room temp reduction | only LiAlH4 able to reduce
50
# Acid Chloride to ester R-COCl → R-COO-R
anhydrous CH3**OH** room temp Condensation (White fumes HCl)
51
# Nitrile to Carboxylic acid and salt R-CN → R-COOH
H2SO4 (aq), heat Acidic Hydrolysis
52
# Nitrile to amine R-CN → R-NH2
LiAlH 4 in dry ether, room temp or H2 (g), Ni, heat Reduction | NaBH4 unable to reduce
53
# Amide to Carboxylic acid and salt R-NHCO-R → R-NH3 + R-COOH
H2SO4 (aq), heat Acidic Hydrolysis
54
# Amide to salt and ammonia H-NHCO-R → NH3 + R-COOH
NaOH(aq), heat Alkaline Hydrolysis
55
# Amide to amine R-NHCO-R → R-NH3
LiAlH 4 in dry ether, room temp Reduction | NaBH4 are not able to reduce amide to amine

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