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Synthetic routes Flashcards

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1
Q

Benzene to Nitrobenzene

A

Reaction: Nitration
Mechanism: Electrophilic Substitution
Conditions: 1- Multiple Nitration Heat above 55 c
2- conc H2SO4 (catalyst)
3- conc HNO3
4- Mononitration Below 55 c kk

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2
Q

Benzene to Phenylketone

A 
Reaction: Actylation 
Mechanism: Electrophilic Substitution 
Conditions: 1- AlCl3 (catalyst)
                    2-Acyl chloride 
                    3-Dry ether
                    4-Heat Under Reflux
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3
Q

Nitrobenzene to Phenylamine

A

Reaction: Reduction
Conditions: 1- conc HCl (catalyst/Reducing agent)
2- Sn/Tin (catalyst/Reducing agent )
3-Heat Under Reflux
4- aqueous NaOH

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4
Q

Phenylamine to N-Phenylethanamide

A

Mechanism: Nucleophilic Addition-Elimination
Conditions: 1- CH3COCl
2- 25 c

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5
Q

Alkane to Halogenoalkane

A

Reaction: Photochemical
Mechanism: Free Radical Substitution
Conditions: 1- UV Light
2- Halogen (X2)

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6
Q

Halogenoalkane to Alcohol

A

Mechanism: Nucleophilic Substitution
Conditions: 1- Warm aqueous NaOH
2- Heat Under Reflux

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7
Q

Halogenoalkane to Nitrile

A

Mechanism: Nucleophilic Substitution
Conditions: 1- aqueous KCN
2- Ethanol
3- Heat Under Reflux

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8
Q

Halogenoalkane to Primary Amine

A

Mechanism: Nucleophilic Substitution
Conditions: 1- warm conc excess ethanolic NH3
2- Sealed Tube
Increase conc of warm excess ethanolic NH3 relative to Conc of Halogenoalkane so less likely chance halogenoalkane will react with an newly produced amine and more likely tor react with NH3

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9
Q

Primary Amine to Secondary Amine /Tertiary Amine/ Quaternary Ammonium Salts

A

Mechanism: Nucleophilic Substitution
Conditions: 1- warm conc excess ethanolic NH3
2- Sealed Tube
Decrease conc of warm excess ethanolic NH3 relative to Conc of Halogenoalkane so more likely chance halogenoalkane will react with an newly produced amine and less likely to react with NH3

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10
Q

Nitrile to Primary Amine

A 
Reaction: Reduction 
IN LAB 
Conditions 1-LiAlH4 (reducing agent)
                   2-dry ether
                   3- dilute H2SO4 (Catalyst)

INDUSTRY-Catalytic Hydrogenation 
Conditions: 1- Ni (catalyst)
                    2-Hydrogen gas 
                    3- High Temp
                    4- High pressure
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11
Q

Halogenoalkane to Alkene

A 
Reaction: Dehydration + condensation 
Mechanism: Elimination
Conditions: 1- conc NaOH/KOH
                    2- Warm Ethanol 
                    3-Heat Under Reflux
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12
Q

Alkene to Halogenoalkane

A

Mechanism: Electrophilic Addition
Conditions: 1- HX/X2
2- 25 c

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13
Q

Alkene to Dibromoalkane

A

Reaction: Oxidation
Mechanism: Electrophilic addition
Conditions: 1-Br2/bromine water
2- 25 c

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14
Q

Alkene to Alcohol

A 
Reaction: Hydration+ Hydrolysis +
Mechanism: Electrophilic Addition 
Conditions: 1- H3PO4 (catalyst)
                    2-steam 
                    3-300 c
                    4-60 atm
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15
Q

Glucose to Alcohol

A

Reaction: Fermentation of Glucose/ Exothermic
Conditions: 1- Yeast
2- 30-40 c
3- Anaerobic

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16
Q

Alcohol to Alkene

A

Reaction: Dehydration + Condensation +
Mechanism: Elimination
Conditions: 1-Hot/Heat
2-excess conc H2SO4 (catalyst)

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17
Q

Primary Alcohol to Aldehyde

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A

Reaction: Oxidation
Conditions: 1-Heat Under DISTILLATION
2-acidified K2Cr2O7 (oxidising agent)
3-dilute H2SO4

18
Q

Primary Alcohol to Carboxylic Acid

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A

Reaction: Oxidation
Conditions: 1-Heat Under REFLUX
2-acidified K2Cr2O7 (oxidising agent)
3-dilute H2SO4

19
Q

Secondary Alcohol to Ketone

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A

Reaction: Oxidation
Conditions: 1-Heat Under Reflux
2-Acidified K2Cr2O7 (oxidising agent)
3-dilute H2SO4

20
Q

Aldehyde to Primary Alcohol

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A 
Reaction: Reduction
Mechanism: Nucleophilic Addition
conditions: 1-NaBH4 (reducing agent)
                   2-Water
                   3-Methanol
21
Q

Ketone to Secondary Alcohol

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A 
Reaction: Reduction 
Mechanism: Nucleophilic Addition 
Conditions: 1-NaBH4 (reducing agent)
                    2-Water
                    3-Methanol
22
Q

Aldehyde to Carboxylic Acid

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A

Reaction: Oxidation
Conditions: 1-Heat Under Reflux
2-acidified K2Cr2O7
3-dilute H2SO4

23
Q

Aldehyde to Hydroxynitrile

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A

Mechanism: Nucelophilic Addition
Conditions: 1-acidified aqeuous KCN
2-dilute H2SO4
3-25 c

24
Q

Ketone to Hydroxynitrile

Study These Flashcards
A

Mechanism: Nucleophilic Addition
Conditions: 1- acidified aqueous KCN
2-dilute H2SO4
3-25 c

25
Carboxylic Acid to Ester
Reaction: Esterfication/Condensation Conditions: 1-Heat Under Reflux 2-Alcohol 3-conc H2SO4 (Catalyst)
26
Ester to Carboxylic Acid
Reaction: Acid Hydrolysis Conditions: 1-Heat under Reflux 2-dilute H2SO4 (catalyst) Reaction: Base Hydrolysis Conditions: 1-Heat Under Reflux 2-dilute aqueous NaOH (catalyst)
27
Biodiesel (Methyl Esters)
Reaction: Base Hydrolysis 1-KOH (Catalyst) 2-methanol
28
Acyl Chloride to Carboxylic Acid
Reaction: Mechanism: Nucleophilic Addition-Elimination Conditions: 1- water 2- 25 c
29
Acyl Chloride to Ester
Mechanism: Nucleophilic Addition-Elimination Conditions: 1- alcohol 2- 25 c
30
Acyl Chloride to Primary amide
Mechanism: Nucleophilic Addition-Elimination Conditions: 1- NH3 2- 25 c
31
Acyl Chloride to N-Substituted Amide
Mechanism: Nucleophilic Addition-Elimination Conditions: 1- amine 2- 25 c
32
Acid Anhydride to Carboxylic Acid
Reactions: Hydrolysis Conditions: 1- Water 2- 25 c
33
Acid Anhydride to Ester
Reactions: Acetylation Conditions: 1- Alcohol 2- 25 c
34
Acid Anhydride to Primary Amide
Reaction: Acetylation Conditions: 1- NH3 2- 25 c
35
Acid Anhydride to N-Substituted Amide
Reaction: Acetylation Conditions: 1-Amine 2- 25 c
36
Alkene to Alcohol with Alkyl hydrogensulfate intermediate
Reaction: Hydration + Hydrolysis Mechanism: Electrophilic Additions Conditions:STEP 1-conc H2SO4 (catalyst) STEP 2-cold water + warm up
37
Hydrocarbons to alkenes
Thermal Cracking 1-High Temp 2-High Pressure
38
Hydrocarbons to Aromatic Hydrocarbons/Alkanes
Catalytic Cracking Zeolite Catalyst 1-Slight/Moderate Pressure 2-High Temp
39
Hydroxynitrile to Carboxylic acid
Reaction: Acid Hydrolysis Conditions: 1-Heat under Reflux 2-dilute aqueous H2SO4 (catalyst) Reaction: Base Hydrolysis Conditions: 1-Heat Under Reflux 2-dilute aqueous NaOH (catalyst)
40
Advantages of Using Ethanoic Anhydride over Ethanoyl Chloride in making aspirin
``` 1-Cheaper 2-Doesn't produce toxic HCl 3-less corrosive 4-reacts more slowly with water 5-less easily hydrolysed 6-less violent reaction ```
41
Advantages of using ethanoyl Chloride over Ethanoic Anhydride in making aspirin
``` 1-faster Rate 2-Not reversible 3-bigger yield 4-purer product 5-no acid catalyst needed ```

Synthetic Routes (5 decks)

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