Organic Reactions Flashcards by Christopher Gibson

Alkene to Alkane
Type of reaction - reagents - conditions

Addition - H2 (g), Ni catalyst, 150 degrees

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Alkane to CO2 and H2O

Type of reaction - reagents - conditions

complete combustion - N/A - excess oxygen

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Alkane to halogneoalkane Type of reaction - reagents - conditions

Free radical substitution - halogen gas - UV light

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Halogenoalkane to alkene

Type of reaction - reagents - conditions

Elimination - ethanolic NaOH - reflux

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Alkene to halogenoalkane Type of reaction - reagents - conditions

Electrophilic substitution - X-H - N/A

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Alkene to Dihalogenoalkane Type of reaction - reagents - conditions

Electrophilic addition - X2 - N/A

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Alkene to alcohol
Type of reaction - reagents - conditions

Electrophilic addition - stream, conc H3PO4 - 100 degrees (for steam)

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Alcohol to Alkene (2 methods)

Type of reaction - reagents - conditions

Elimination - conc. H3PO4 - 180. degrees
Elimination - Al2O3 - heat

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Alkene to diol

Type of reaction - reagents - conditions

N/A - acidified potassium permanganate (KMnO4) - N/A

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Alkane to Alkene (2 types)

Type of reaction - products - conditions

Thermal Cracking - Alkenes and alkanes - 400 < T < 900, 7000 kPa
Catalytic Cracking - branched alkanes, cycloalkanes and aromatic hydrocarbons - zeolite catalyst, 450, slight pressure

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Halogenoalkane to grignard reagent

Type of reaction - reagents - conditions

N/A - Mg in dry ether - reflux

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Halogenoalkane to 1 amine

Type of reaction - reagents - conditions

Nucleophilic substitution - XS NH3 in ethanol - sealed tube, heat

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Halogenoalkane to nitrile

Type of reaction - reagents - conditions

Nuc Sub - aq/ethanolic mix of KCN - reflux

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Nitrile to carboxylic acid (2 ways)

Type of reaction - reagents - conditions

Hydrolysis - Dilute HCl - reflux
Hydrolysis - aq NaOH then acid - reflux

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Nitrile to 1 amine (2 ways)

Type of reaction - reagents - conditions

Reduction - LiAlH4 in dry ether - N/A
Reduction - H2 - Ni, 150

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Halogenoalkane to Alcohol

Type of reaction - reagents - conditions

Nuc sub - aqueous NaOH or KOH - warm

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Alcohol to Halogenoalkane

Type of reaction - reagents - conditions

Chlorination - PCl5 - room temp
Bromination - 50% conc H2SO4, KBr - reflux
Iodination - damp red P, I2 - warm

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Alcohol to acid/ aldehyde/ ketone

Type of reaction - reagents - conditions

Oxidation- acidified K2Cr2O7 - reflux or distill depending on required product

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Ketone/ aldehyde/ acid to alcohol

Type of reaction - reagents - conditions

Reduction - LiAlH4 in dry ether - N/A

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What can LiAlH4 reduce and what are the conditions for its use

Polar double bonds - dry ether

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Alcohol to ester

Type of reaction - reagents - conditions

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Condensation (esterification) - carboxylic acid, conc H2SO4 - reflux

Ester hydrolysis in acid

Type of reaction - reagents - conditions - products

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Hydrolysis - water, HCl - reflux - equilibrium mix of ester, acid and alcohol

Ester hydrolysis in alkali

Type of reaction - reagents - conditions - products

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Hydrolysis - water, NaOH - reflux - carboxylate ion and alcohol

Acid to acyl chloride

Type of reaction - reagents - conditions - other products

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Substitution - PCl5 - N/A - POCl3 + HCl

Acyl chloride to carboxylic acid Type of reaction - reagents - conditions

Nucleophilic addition elimination - water - N/A

Acyl chloride to ester Type of reaction - reagents - conditions

Nucleophilic addition elimination - alcohol - anhydrous

Acyl chloride to amide (primary) Type of reaction - reagents - conditions

Nucleophilic addition elimination - ammonia - N/A

Acyl chloride to secondary amide Type of reaction - reagents - conditions

Nucleophilic addition elimination- primary amine - N/A

Describe the first and second steps of Nucleophilic addition elimination of water and ethanoyl chloride

1. Lone pair on O attacks delta+ C and double bond breaks with electrons going to O (addition) 2. H lost from OH2 group, double bond reforms and Cl eliminated (elimination)

How are polyesters formed (3 ways) Type of reaction - reagents - conditions

Polymerisation - diol, dicarboxylic acid- reflux, H2SO4 Polymerisation - diol, diacyl chloride - N/A Polymerisation - hydroxyl group and a carboxylic acid group on either end of the molecule

Why are ester polymers biodegradable

The ester linkage is susceptible to hydrolysis

Two reactants to make polyamides

Diamine and dicarboxylic acid

3 pieces of evidence against the kekule structure

1. All bond lengths are the same 2. Enthalpy of hydrogenation is a less negative value than expected if it was 3 double bonds 3. Benzene doesn’t undergo addition reactions

What species attacks benzene rings

Electrophile

Why don’t benzene react via addition

As they don’t want to lose the stability of the delocalised ring

How to form a nitro group Type of reaction - reactants - how both reaction steps happen

Acid base - nitric acid and sulphuric acid 1. Nitric acid acts as base and H2NO3+ forms 2. Dissociation into water and nitronium ion

Benzene to Nitrobenzene Type of reaction - reactants - conditions

Electrophilic substitution - nitric acid and benzene - 50 degrees and conc. H2SO4

Why is nitration of benzene done at 50 degrees

Higher gives multiple substitutions and lower reduces rate of reaction too much

What’s the electrophile in friedel-crafts acylation

Acylium ion

How is an acylium ion formed

Acyl chloride + AlCl3 —> AlCl4- + acyclium ion

Acyl group substitution onto benzene ring Type of reaction - reactants - conditions

Electrophilic substitution - acyl chloride, AlCl3 - anhydrous

Bromination of benzene Type of reaction - reactants - conditions

Electrophilic substitution - Br2, FeBr3 catalyst, - catalyst made in situ from bromine and iron filings

How is the catalyst formed in bromination of benzene Reactants and equation

Iron fillings and bromine 2Fe + 3Br2 —> 2FeBr3

What’s the Electrophile in Bromination of benzene

Bromonium Br+

What kind of group is the OH in phenol and why

(2,4,6) Activating - adds electron density to the ring (lone pair on O is involved in the aromatic delocalisation system)

Phenol + bromine water Characteristics of product

2,4,6-tribromophenol - white ppt with antiseptic smell

Phenol nitration Type of reaction - reactants - conditions

Electrophilic substitution - dilute nitric acid - 50 degrees in concentrated sulfuric acid

How do phenols behave differently to alcohols

They are weak acids (less so than carboxylic acids) and don’t undergo Nucleophilic substitution reactions

Why can phenol behave as an acid

Delocalisation from the ring can stabilises A-

How is friedelcrafts alkylation different to acylation

A Halogenoalkane is used rather than an acyl chloride

Organic Reactions Flashcards

(50 cards)