962 chemistry [ppu_stpm] semester 3 topics-syllabus

7/30/2019 962 Chemistry [PPU_STPM] Semester 3 Topics-Syllabus

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[PPU] Semester 3 Topics-Syllabus

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962CHEMISTRY

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THIRD TERM

TopicTeachingPeriod

Learning Outcome

14 Introduction to OrganicChemistry

21

14.1 Bonding of the carbonatoms: the shapes ofethane, ethene, ethyneand benzene molecules

4 Candidates should be able to:

(a) use the concept ofsp3,sp

2andsp

hybridisations in carbon atoms to describe thebonding and shapes of molecules asexemplified by CH4, C2H4, C2H2 and C6H6;

(b) explain the concept of delocalisation ofelectrons in benzene ring.

14.2 General, empirical,molecular andstructural formulae oforganic compounds


(a) state general, empirical, molecular andstructural formulae of organic compounds;

(b) determine empirical and molecular formulae oforganic compounds.

14.3 Functional groups:classification andnomenclature


(a) describe the classification of organiccompounds by functional groups and the

nomenclature of classes of organic compoundsaccording to the IUPAC rules of the followingclasses of compounds:

(i) alkanes, alkenes, alkynes and arenes,

(ii) haloalkanes,

(iii) alcohols (including primary, secondaryand tertiary) and phenols,

(iv) aldehydes and ketones,

(v) carboxylic acids and their derivatives

(acyl chlorides, amides and esters),

(vi) primary amines, amino acids andprotein.

14.4 Isomerism: structuraland stereoisomerism


(a) define structural and stereoisomerism(geometrical and optical);

(b) explain the meaning of a chiral centre inoptical isomerism;

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Learning Outcome

(c) classify isomers as structural, cis-trans andoptical isomers;

(d) identify chiral centres and/orcis-transisomerism in a molecule of given structuralformula;

(e) deduce the possible isomers for an organiccompound of known molecular formula.

14.5 Free radicals,nucleophiles andelectrophiles


(a) describe homolytic and heterolytic fissions;

(b) define the terms free radical, nucleophile and

electrophile;(c) explain that nucleophiles such as OH , NH3,

H2O, Br , I and carbanion are Lewis bases;

(d) explain that electrophiles such as H+, NO2+,

Br2, A1C13, ZnC12, FeBr3, BF3 and carboniumion are Lewis acids.

14.6 Molecular structureand its effect on

physical properties


(a) describe the relationship between the size ofmolecules in the homologous series and the

melting and boiling points;

(b) explain the forces of attraction betweenmolecules (van der Waals forces and hydrogenbonding).

14.7 Inductive andresonance effect


(a) explain inductive effect which can determinethe properties and reactions of functionalgroups;

(b) use inductive effect to explain why functional

groups such as NO2, CN, COOH, COOR,>C=O, SO3H, X (halogen), OH, OR,

NH2, C6H5 are electron acceptors whereasR(alkyl) is an electron donor;

(c) explain how the concept of induction canaccount for the differences in acidity betweenCH3COOH, C1CH2COOH, C12CHCOOH and

Cl3CCOOH; between C1CH2CH2CH2COOHand CH3CH2CHClCOOH;



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Learning Outcome

(d) use the concept of resonance to explain thedifferences in acidity between CH3CH2OH and

C6H5OH, as well as the differences in basicitybetween CH3NH2 and C6H5NH2.

15 Hydrocarbons

15.1 Alkanes

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(a) write the general formula for alkanes;

(b) explain the construction of the alkane series(straight and branched), and IUPACnomenclature of alkanes for C1 to C10;

(c) describe the structural isomerism in aliphaticalkanes and cis-trans isomerism incycloalkanes;

(d) state the physical properties of alkanes;

(e) define alkanes as saturated aliphatichydrocarbons;

(f) name alkyl groups derived from alkanes and

identify primary, secondary, tertiary andquartenary carbons;

(g) explain the inertness of alkanes towards polarreagents;

(h) describe the mechanism of free radical

substitution as exemplified by the chlorinationof methane (with particular reference to theinitiation, propagation and terminationreactions);

(i) describe the oxidation of alkane with limitedand excess oxygen, and the use of alkanes asfuels;

(j) explain the use of crude oil as a source of

aliphatic hydrocarbons;

(k) explain how cracking reactions can be used toobtain alkanes and alkenes of lowerMrfromlarger hydrocarbon molecules;

(l) discuss the role of catalytic converters inminimising air pollution by oxidising CO toCO2 and reducing NOx to N2;

(m) explain how chemical pollutants from thecombustion of hydrocarbon affect air qualityand rainwater as exemplified by acid rain,

photochemical smog and greenhouse effect.



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15.2 Alkenes 6 Candidates should be able to:

(a) write the general formula for alkenes;

(b) name alkenes according to the IUPACnomenclature and their common names for C1

to C5;

(c) describe structural and cis-trans isomerism inalkenes;

(d) state the physical properties of alkenes;

(e) define alkenes as unsaturated aliphatichydrocarbons with one or more double bonds;

(f) describe the chemical reactions of alkenes asexemplified by the following reactions ofethene:

(i) addition of hydrogen, steam, hydrogenhalides, halogens, bromine water andconcentrated sulphuric acid,

(ii) oxidation using KMnO4, O2/Ag,

(iii) ozonolysis,

(iv) polymerisation;

(g) describe the mechanism of electrophilic

addition in alkenes with reference toMarkovnikovs rule;

(h) explain the use of bromination reaction and

decolourisation of MnO4 ions as simple tests

for alkenes and unsaturated compounds;

(i) explain briefly the importance of ethene as asource for the preparation of chloroethane,epoxyethane, ethane-1,2-diol andpoly(ethane).

15.3 Arenes 8 Candidates should be able to:

(a) name aromatic compounds derived frombenzene according to the IUPACnomenclature, including the use ofortho,meta andpara or the numbering of substitutedgroups to the benzene ring;

(b) describe structural isomerism in arenes;



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(c) describe the chemical reactions of arenes asexemplified by substitution reactions of

haloalkanes and acyl chloride (Friedel-Craftsreaction), halogen, conc. HNO3/conc. H2SO4and SO3 with benzene and methylbenzene(toluene);

(d) describe the mechanism of electrophilicsubstitution in arenes as exemplified by thenitration of benzene;

(e) explain why benzene is more stable thanaliphatic alkenes towards oxidation;

(f) describe the reaction between alkylbenzene

and hot acidified KMnO4;(g) determine the products of halogenation of

methylbenzene (toluene) in the presence of

(i) Lewis acid catalysts,

(ii) light;

(h) explain the inductive effect and resonance

effect of substituted groups ( OH, C1, CH3,

NO2, COCH3, NH2) attached to thebenzene ring towards further substitutions;

(i) predict the products in an electrophilicsubstitution reaction when the substitutedgroup in benzene is electron accepting orelectron donating;

(j) explain the uses of arenes as solvents;

(k) recognise arenes as carcinogen.

16 Haloalkanes 8 Candidates should be able to:

(a) write the general formula for haloalkanes;

(b) name haloalkanes according to the IUPAC

nomenclature;

(c) describe the structural and optical isomerism inhaloalkanes;

(d) state the physical properties of haloalkanes;

(e) describe the substitution reactions ofhaloalkanes as exemplified by the followingreactions of bromoethane: hydrolysis, theformation of nitriles and the formation of

primary amines;



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(f) describe the elimination reactions ofhaloalkanes;

(g) describe the mechanism of nucleophilicsubstitution in haloalkanes (SN1 and SN2);

(h) explain the relative reactivity of primary,secondary and tertiary haloalkanes;

(i) compare the reactivity of chlorobenzene andchloroalkanes in hydrolysis reactions;

(j) explain the use of haloalkanes in the synthesisof organomagnesium compounds (Grignardreagents), and their use in reactions withcarbonyl compounds;

(k) describe the uses of fluoroalkanes andchlorofluoroalkanes as inert substances foraerosol propellants, coolants and fire-

extinguishers;

(l) state the use of chloroalkanes as insecticidesuch as DDT;

(m) describe the effect of chlorofluoroalkanes inthe depletion of the ozone layer, and explain

its mechanism.

17 Hydroxy Compounds

17.1 Introduction to

hydroxy compounds

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(a) write the general formula for hydroxycompounds;

(b) name hydroxy compounds according to theIUPAC nomenclature;

(c) describe structural and optical isomerism inhydroxy compounds;

(d) state the physical properties of hydroxycompounds.

17.2 Alcohols 6 Candidates should be able to:

(a) classify alcohols into primary, secondary andtertiary alcohol;

(b) classify the reactions of alcohols whereby the

RO H bond is broken: the formation of analkoxide with sodium, esterification, acylation,

oxidation to carbonyl compounds andcarboxylic acids;



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(c) classify the reactions of alcohols whereby the

R OH is broken and OH is replaced by other

groups: the formation of haloalkanes and thedehydration to alkenes and ethers;

(d) explain the relative reactivity of primary,secondary and tertiary alcohols as exemplifiedby the reaction rate of such alcohols to givehaloalkanes, and the reaction products ofKMnO4/K2Cr2O7 oxidation in the presence ofsulphuric acid;

(e) explain the reaction of alcohol with the

structure CH3CH(OH) with alkaline aqueoussolution of iodine to form triiodomethane;

(f) describe the laboratory and industrialpreparation of alcohol as exemplified byethanol from the hydration of ethane;

(g) describe the synthesis of ethanol byfermentation process;

(h) state the uses of alcohols as antiseptic, solventand fuel.

17.3 Phenols 5 Candidates should be able to:

(a) explain the relative acidity of water, phenoland ethanol with particular reference to the

inductive and resonance effects;

(b) describe the reactions of phenol with sodiumhydroxide, sodium, acyl chlorides andelectrophilic substitution in the benzene ring;

(c) describe the use of bromine water and aqueousiron(III) chloride as tests for phenol;

(d) describe the cumene process in themanufacture of phenol;

(e) explain the use of phenol in the manufacture ofcyclohexanol, and hence, nylon-6,6.

18 Carbonyl Compounds 8 Candidates should be able to:

(a) write the general formula for carbonylcompounds: aliphatic and aromatic aldehydes

and ketones;

(b) name aliphatic and aromatic aldehydes andketones according to the IUPACnomenclature;



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(c) describe structural and optical isomerism incarbonyl compounds;

(d) state the physical properties ofaliphatic andaromatic aldehydes and ketones;

(e) write the equations for the preparation ofaldehydes and ketones;

(f) explain the reduction reactions of aldehydesand ketones to primary and secondary alcohols

respectively through catalytic hydrogenationreaction and with LiA1H4;

(g) explain the use of 2,4-dinitrophenylhydrazinereagent as a simple test to detect the presence

of >C=O groups;

(h) explain the mechanism of the nucleophilicaddition reactions of hydrogen cyanide with

aldehydes and ketones;

(i) explain the oxidation of aldehydes;

(j) differentiate between aldehyde and ketone

based on the results of simple tests asexemplified by Fehlings solution and Tollens

reagent;

(k) explain the reactions of carbonyl compounds

with the structure CH3 C=O with alkaline

aqueous solution of iodine to givetriiodomethane (iodoform test);

(l) explain that natural compounds such asglucose, sucrose and other carbohydrateswhich have the >C=O group;

(m) explain the characteristics of glucose as areducing sugar.

19 Carboxylic Acids and their

Derivatives

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19.1 Carboxylic acid 4 Candidates should be able to:

(a) write the general formula for aliphatic andaromatic carboxylic acids;

(b) name carboxylic acids according to the IUPACnomenclature and their common names forC1toC6;

(c) describe structural and optical isomerism incarboxylic acids;



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(d) state the physical properties of carboxylicacids;

(e) write the equations for the formation ofcarboxylic acids from alcohols, aldehydes andnitriles;

(f) describe the acidic properties of carboxylicacids as exemplified by their reactions withmetals and bases to form salts;

(g) explain the substitution of the OH in

carboxylic acids by the nucleophiles OR and

C1 to form esters and acyl chloridesrespectively;

(h) describe the reduction of carboxylic acids to

primary alcohols;

(i) describe the oxidation and dehydration ofmethanoic and ethanedioic acids (oxalic acid);

(j) state the uses of carboxylic acids in food,perfume and polymer industries.

19.2 Acyl chlorides 2 Candidates should be able to:

(a) write the general formula for acyl chlorides;

(b) name acyl chlorides according to the IUPACnomenclature;

(c) describe structural and optical isomerism inacyl chlorides;

(d) state the physical properties of acyl chlorides;

(e) explain the ease of hydrolysis of acyl chloridescompared to chloroalkanes;

(f) describe the reactions of acyl chlorides withalcohols, phenols and primary amines.

19.3 Esters 2 Candidates should be able to:

(a) write the general formula for esters;

(b) name esters according to the IUPACnomenclature;

(c) describe structural and optical isomerism inesters;

(d) state the physical properties of esters;(e) describe the preparation of esters by the

reactions of acyl chlorides with alcohols and

phenols;



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(f) describe the acid and base hydrolysis of esters;

(g) describe the reduction of esters to primaryalcohols;

(h) state the uses of esters as flavourings,preservatives and solvents.

19.4 Amides 2 Candidates should be able to:

(a) write the general formula for amides;

(b) name amides according to the IUPAC

nomenclature;

(c) describe structural and optical isomerism in

amides;

(d) state the physical properties of amides;

(e) describe the preparation of amides by thereaction of acyl chlorides with primary amines;

(f) describe the acid and base hydrolysis ofamides.

20 Amines, Amino Acids and

Proteins

20.1 Amines

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4 Candidates should be able to:(a) write the general formula for amines;

(b) name amines according to the IUPACnomenclature and their common names;

(c) describe structural and optical isomerism inamines;

(d) state the physical properties of amines;

(e) classify amines into primary, secondary andtertiary amines;

(f) explain the relative basicity of ammonia,ethanamine and phenylamine (aniline) in termsof their structures;

(g) describe the preparation of ethanamine by thereduction of nitriles, and phenylamine by thereduction of nitrobenzene;

(h) explain the formation of salts when aminesreact with mineral acids;

(i) differentiate primary aliphatic amines fromprimary aryl (aromatic) amines by theirrespective reactions with nitric(III) acid(nitrous acid) and bromine water;



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(j) explain the formation of dyes by the couplingreaction of the diazonium salt as exemplified

by the reaction of benzenediazonium chloridewith phenol.

20.2 Amino acids 3 Candidates should be able to:

(a) write the structureand general formula for

-amino acids;

(b) name -amino acids according to the IUPACnomenclature and their common names;

(c) describe structural and optical isomerism inamino acids;

(d) state the physical properties of -amino acids;

(e) describe the acid and base properties of

-amino acids;

(f) describe the formation of zwitterions;

(g) explain the peptide linkage as amide linkageformed by the condensation between two or

more -amino acids as exemplified byglycylalanine and alanilglycine.

20.3 Protein 1 Candidates should be able to:

(a) identify the peptide linkage in the primarystructure of protein;

(b) describe the hydrolysis of proteins;

(c) state the biological importance of proteins.

21 Polymers 8 Candidates should be able to:

(a) state examples of natural and syntheticpolymers;

(b) define monomer, polymer, repeating unit,homopolymer and copolymer;

(c) identify the monomers in a polymer;

(d) describe condensation polymerisation asexemplified by terylene and nylon-6,6;

(e) describe addition polymerisation asexemplified by poly(ethene)/polyethylene/polythene, poly(phenylethene)/polystyrene andpoly(chloroethene)/polyvinylchloride;



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(f) state the role of the Ziegler-Natta catalyst inthe addition polymerisation process;

(g) explain the classification of polymers asthermosetting, thermoplastic and elastomer;

(h) identify isoprene (2-methylbuta-1,3-diene) asthe monomer of natural rubber;

(i) describe the two isomers inpoly(2-methylbuta-1,3-diene) in terms of the

elastic cis form (from theHevea brasiliensistrees) and the inelastic trans form (from the

gutta-percha trees);

(j) state the uses of polymers;

(k) explain the difficulty in the disposal ofpolymers;

(l) outline the advantages and disadvantages ofdumping polymer-based materials in rivers andseas.