Mechanism Summary for A-level AQA Chemistry
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1 Mechanism Summary for Alevel AQA hemistry Electrophilic Addition of Alkenes with omine Electrophilic Addition of Alkenes with sulphuric acid 3 S S 2 S 2 Electrophilic Addition of Alkenes with hydrogen bromide Elimination of alogenoalkanes with ethanolic hydroxide ions Acid catalysed elimination mechanism alcohols alkenes The comes from the conc 2 S 4 or conc 3 P 4 3 Acid catalysed addition mechanism for hydration of ethene The comes from the conc 3 P 4 Nucleophilic Substitution of alogenoalkanes with aqueous hydroxide ions. 3 3 Nucleophilic Substitution of alogenoalkanes with cyanide ions. 3 3 N N Free Radical Substitution of Alkanes with omine STEP NE Initiation Essential condition UV light 2 2. STEP TW Propagation STEP TREE Termination
2 Nucleophilic Substitution reactions of ammonia/amines Reaction 1 with ammonia forming primary amine 3 3 N 3 3N 3 N 2 N 3 3 N 2 N 4 Reaction 2 forming secondary amine The amine formed in the first reaction has a lone pair of electrons on the nitrogen and will react further with the haloalkane N N N N 2 3 N 4 N 3 Diethylamine Reaction 3 forming a tertiary amine N N 2 3 N N N 2 3 triethylamine Reaction 4 forming a quaternary ammonium salt N N Tetraethylammonium ion
3 Mechanism Summary for ALevel AQA hemistry Nucleophilic Addition Mechanism from water or weak acid l l 3 3 l N 3 Electrophilic Substitution 3 N 2 l 3 Equation for Formation of electrophile N S 4 N 2 2S 4 3 N 2 N 2 N 2 Nucleophilic Addition Mechanism 3 N l l 3 N 2 3 l N l N N from sulphuric acid N 2 3 Electrophilic Substitution Equation for Formation of the electrophile. All 3 3 l 3 All N 2 3 S 4 2 S 4 All 4 All 3 l
4 Reaction Summary for Alevel AQA hemistry poly(alkene) dihalogenoalkane K aqueous under reflux Nu Sub diol high pressure catalyst Step 1 2 S 4 Step 2 2 warm hydrolysis alcohol alkene conc. 2 S 4 or conc. 3 P 4 Elimination, dehydration 2, l 2 K aqueous under reflux, l K alcoholic under reflux Elimination halogenoalkane alkane 2, l 2 UV light Fr Sub NaB 4 If primary Na 2 r 2 7 / and distill partial ox aldehyde (If primary) Na 2 r 2 7 / under reflux excess oxidising agent xidation carboxylic acid If secondary Na 2 r 2 7 / oxidation ketone NaN 2 S 4 Nu Add NaB 4 hydroxynitrile Alcohol 2 S 4 aboxylic acid 2 S 4 ester KN in ethanol/ water mixture under reflux nitrile Esters and amides can be hydrolysed by Na and acids LiAl 4 in ether haloalkane 2 o amine 3 o amine Quaternary salt 1 o amine Alcoholic N 3 under pressure 1 o amine Acyl chloride secondary amide 2 Alcohol Acyl chloride/ acid anhydride N 3 Primary amide N Goalby chemrevise.org 4
5 Aromatic synthetic routes N 2 conc nitric acid conc sulphuric acid Electrophilic substitution Sn and l N 2 3 l Nu sub N 3 acyl chloride in the presence of anhydrous aluminium chloride catalyst Electrophilic substitution 3 NaN 2 S 4 Nu Add N 3 l Nucleophilic addel N 3 3 NaB 4 3 LiAl 4 2 N S N Goalby chemrevise.org 5
Mechanisms. . CCl2 F + Cl.
Mechanisms 1) Free radical substitution Alkane à halogenoalkane Initiation: Propagation: Termination: Overall: 2) Ozone depletion UV light breaks the C Cl bond releasing chlorine radical CFCl 3 F à. CCl2
Acyl chloride/ acid anhydride
3.14 Synthetic routes poly(alkene) dihalogenoalkane KH aqueous under reflux Nu Sub diol high pressure catalyst Step 1 H 2 S 4 EAdd Step 2 H 2 warm hydrolysis alcohol alkene conc. H 2 S 4 or conc. H 3 P
dihalogenoalkane H 2, Nickel Catalyst addition/reduction HBr, HCl room temp KOH alcoholic heat under reflux Elimination
Synthetic Routes dihalogenoalkane K aqueous heat under reflux Nucleophilic substitution poly(alkene) high pressure atalyst polymerization LiAl 4 Reduction 2 (g) atalyst: onc 3 P 4 LiAl 4 Reduction alkene
Carbonyls. Aldehydes and Ketones N Goalby chemrevise.org. chemrevise.org
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dihalogenoalkane H 2, KOH alcoholic heat under reflux Elimination PCl 5, PBr 3, PI 3 Heat under reflux substitution KOH aqueous heat under reflux
7. AS mechanisms dihalogenoalkane poly(alkene) 2, l 2 room temp Electrophilic addition KO aqueous heat under reflux Nucleophilic substitution high pressure atalyst polymerization alkene KMnO 4 oxidation
HALOGENOALKANES (HALOALKANES) Structure Contain the functional group C-X where X is a halogen (F,Cl,Br or I)
aloalkanes 2812 1 ALOGENOALKANES (ALOALKANES) Structure ontain the functional group X where X is a halogen (F,l, or I) Types alogenoalkanes halogen is attached to an aliphatic skeleton alkyl group aloarenes
23 Synthetic Routes. Chirality in pharmaceutical synthesis. N Goalby chemrevise.org 1
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dihalogenoalkane H 2, Nickel Catalyst addition/reduction HBr, HCl room temp KOH alcoholic heat under reflux Elimination
20 Synthetic Routes dihalogenoalkane K aqueous heat under reflux Nucleophilic substitution poly(alkene) high pressure atalyst polymerization LiAl 4 Reduction 2 (g) atalyst: onc 3 P 4 LiAl 4 Reduction alkene
HALOALKANES (HALOGENOALKANES) Structure Contain the functional group C-X where X is a halogen (F, Cl, Br or I)
alogenoalkanes 1 ALOALKANES (ALOGENOALKANES) Structure ontain the functional group X where X is a halogen (F, l, or I) Types aloalkanes halogen is attached to an aliphatic skeleton alkyl group aloarenes
HALOGENOALKANES (HALOALKANES) Structure Contain the functional group C-X where X is a halogen (F, Cl, Br or I)
alogenoalkanes F322 1 ALOGENOALKANES (ALOALKANES) Structure ontain the functional group X where X is a halogen (F, l, or I) Types alogenoalkanes halogen is attached to an aliphatic skeleton alkyl group
Organic Chemistry Review: Topic 10 & Topic 20
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Summary of mechanisms. Type of reaction: Nucleophilic subsitution/hydrolysis
S Summary of mechanisms S Summary of mechanisms electrophilic addition Electrophiles: H δ in H (Ni catalyst needed), H δ in H-X; X δ in X ; H δ in H O (g) (conc H 3 PO 4 cat needed); H δ in NH 3 ; H δ
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dihalogenoalkane H 2, Nickel Catalyst KOH alcoholic HBr, HCl Br Cl Elimination KOH aqueous heat under reflux Nucleophilic substitution
7 AS mechanisms dihalogenoalkane poly(alkene) Br 2, 2 KO aqueous room temp Electrophilic addition heat under reflux Nucleophilic substitution high pressure atalyst polymerization alkene KMnO 4 oxidation
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Amines. Types of Amines. chemrevise.org. N Goalby Chemrevise.org. primary amine (one C attached to N) H. Secondary amine (two C s.
Amines Goalby hemrevise.org Types of Amines primary amine (one attached to ) Secondary amine (two s attached to ) 3 2 2 3 name : diethylamine It is also possible to have aromatic amines 2 phenylamine name:
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5. Synthetic Routes dihalogenoalkane poly(alkene) Br 2, l 2 room temp Electrophilic addition K aqueous heat under reflux Nucleophilic substitution high pressure atalyst polymerization alkene KMn 4 oxidation
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LECTURE #22 Thurs., Nov.15, 2007
Provide a rxn sequence to make these as the major products Answers: 1. i Pr-Cl, AlCl 3 2. conc. fuming? H 2 S 4 3. Cl 2, FeCl 3 or AlCl 3 4. dilute H 2 S 4 note: normally aqueous workup after step 1, but