Chapter 1 Chemical Bond

8/13/2019 Chapter 1 Chemical Bond

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RGANIC CHEMISTRY 1

CHM456

MOHD FAZLI MOHAMMAT @ MYAHYAA513 OLD ENGINEERING BLOCK,UiTMTel: 55211354

Paclitaxel (Taxol)anticancerco!o"n#i$olate# %ro t&e

'ar o% t&e !aci%ice* tree


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Co"r$e +"tlineCarbon Compounds and Chemical Bonds1.1 Structure of carbon compounds

1.2 Chemical bonds: ionic and covalent bonds

1.3 Polar and nonpolar molecules: Formal charge and resonance

1.4 Intermolecular forces

1. !"bridi#ation$ %tomic and &olecular orbitals

Introduction to Organic Reactions

2.1 'eactions and mechanisms: substitution$ elimination$ addition andrearrangement

2.2 !omol"sis and heterol"sis of covalent bonds$ homogenic and heterogenic ofbonds

2.3 %cid(base reactions:

2.2.1 Carbocations and carbanions

2.2.2 Strengths of acids and bases: )aand p)a

2.2.3 Structure and acidit": resonance and inductive effects

Stereochemistry

3.1 Isomerism:

3.1.1 Structural and geometric isomers: position$ functional groups$ * and +

3.1.2 ,ptical isomers: chiralit"$ racemic mi-ture$meso compound$ specificrotation

3.2 &olecules ith more than one stereocenter

Alkanes and cycloalkanes

4.1 Structure and /omenclature

4.2 Ph"sical Properties

4.3 0ond 'otation and Conformational %nal"sis of 0utane

4.4 Stabilit" of C"cloalanes: 'ing Strain and Conformation of C"clohe-ane

4. S"nthesis of %lanes: !"drogenation of %lenes and %l"nes$ 'eduction of%l"l !alide$ %l"lation of terminal %l"nes

4. 'eaction of %lanes ith !alogens: Chlorination of &ethane


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Co"r$e +"tlineAlkyl Halides

.1 Structure and Ph"sical Properties of %l"l !alides

.2 /ucleophilic Substitution 'eactions

.2.1 /ucleophiles and eaving roups

.2.2 S/2 'eaction: )inetics$ &echanism and Stereochemistr"

.2.3 S/1 'eaction: &echanism$ Carbocations and Stereochemistr"

.2.4 Factors affecting S/2 and S/1 'eactions

.3 *limination 'eactions of %l"l !alides.3.1 *2'eactions

.3.2 *1'eactions

.4 Substitution versus *limination

Alkenes and Alkynes

.1 %lenes: /omenclature$ Structure and Ph"sical Properties

.2 'eactions and &echanisms

.2.1 S"nthesis of %lenes via*limination 'eactions: 5eh"drohalogenation$5eh"dration$ 5ebromination

.2.2 %ddition 'eactions : and &arovniov6s and %nti&arovniov6s 'ule.3 %l"nes: /omenclature$ Structure and Ph"sical Properties

.4 'eactions and &echanisms

.4.1 %ddition$ !"dration$ ,-idation and 'eduction

Alcohols and Ethers

7.1 Structure$ /omenclature and Ph"sical Properties

7.2 S"nthesis of %lcohols from %lenes

7.3 'eactions of %lcohols$ %lcohols as %cids8 Conversion to %l"l !alides8 ,-idation

to Carbon"l Compounds7.4 S"nthesis and 'eactions of *thers

7. Phenols: Structure and /omenclature8 S"nthesis and 'eactions

Benzene and Aromaticity

9.1 Introduction: 0en#ene$ /omenclature8 Structure and Stabilit"8 !ucel6s 'ule

9.2 ,ther %romatic Compounds and !eteroc"clic %romatic Compounds

9.3 'eactions of %romatic Compounds

9.3.1 *lectrophilic %romatic Substitution

9.3.2 !alogenation8 /itration and Sulfonation

9.3.3 Friedel(Craft6s %l"lation and %c"lation


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Teaching Methodology,ect"re$ an# la'orator $e$$ion$

AssessmentA$$i.nent$ / 10

Te$t$ / 20,a'orator re!ort$ /30inal exaination /40

Recommended TextSoloon$ an# r&le t&E#ition +r.anicC&ei$tr 7ile 3008Morri$on 9o# +r.anic C&ei$trMcM"rra: ; +r.anic C&ei$tr


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7&at i$ +r.anic C&ei$tr


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+r.anic C&ei$tr in Yo"r,i%e

FoodFertilizer, pesticides,preservatives, additives

MaterialsPolymers, coatings,adhesives

Drugs

Aspirin, Viagra, Neuroen

!he entire modern "orldPetrochemicals, environmental chemistry, etc


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T&e a.ic Car'on ato

Difference betweenorganic and inorganicis C-atom ability toform very long chain

(catenation); Inor.anic co!o"n# *ill

'ecoe "n$ta'le a%ter *it&13 or ore ato$

; C=ato$ a'ilit to %or >er$tron. co>alent 'on#


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CA!T"R #$"

%tr&ct&re and 'onding


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Chater - %tr&ct&re and 'onding

"*"CTR#$ C#$+,.RAT,#$

Electron$ re$i#e aro"n# t&e n"cle"$ in #i$crete ener.le>el$ T&e$e ener. $&ell$ contain or'ital$ = a at&eatical!ro'a'ilit t&at an electron *ill exi$t in t&at $!ace +r'ital$are #e$cri'e# ' ?"ant" ec&anic$ in #i$tinct $&a!e$ Sor'ital$ are $!&erical an# ! or'ital$ are $&a!e# lie

#"''ell$

A"%'a" Princi!le = t&e lo*e$t ener. or'ital %ill$ "! %ir$t

Pa"li Excl"$ion Princi!le = onl t*o electron$ can occ"! anor'ital an# t&e "$t 'e o% o!!o$ite

S!in

H"n#@$ R"le = i% t*o or ore or'ital$ o% e?"al ener. area>aila'le t&e are %ille# *it& one electron o% !arallel $!in"ntil all are &al% %ille# +nl t&en *ill electron$ 'e !aire# "!

T&i$ i$ i!ortant in %illin. t&e t&ree ! or'ital$

alence electron$ are t&o$e in t&e o"tero$t ener. $&ell o%


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Chater - 'onding and %tr&ct&re

Ionic 9on#$ = Ato$ &el# to.et&er ' electro$tatic attraction (ion$)

Co>alent 9on#$ = Ato$ $&are electron$ 'et*een t&e = "c& $tron.ert&an ionic 'on#$

Car'on (1$33$33!3) *o"l# &a>e to .ain or lo$e 4 electron$ to ac&ie>ea %ille# $&ell an# i$ t&ere%ore not ea$il ioniBe# Car'on %or$ co>alent

'on#$ rat&er t&an ionic 'on#$

Molec"le = a collection o% ato$ &el# to.et&er ' co>alent 'on#$

,e*i$ Str"ct"re$ = re!re$ent t&e >alence electron$ aro"n# t&e ato '

#ot$ Co>alent 'on#$ are $&o*n *it& t&e t*o electron #ot$D $&are#'et*een t&e ato$

e"lF Str"ct"re$ = Eac& co>alent 'on# i$ re!re$ente# ' a $in.le linein#icatin. t*o $&are# electron$


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Three-Dimensional

+orm&las


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R"%#$A$C"

Re$onance $ta'iliBation i$ o$t i!ortant *&en it $er>e$ to#elocaliBe a c&ar.e o>er t*o or ore ato$ / e. car'onate


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T" %TR.CT.R" #+ M"TA$" A$D "TA$"/ !3HYBRIDZATION

0'R,D1AT,#$

Orbital hybridization: A mathematical approach that inoles the

combining of individual ave functions for s and p orbitals to obtain ave

functions for ne orbitals hybrid atomic orbitals


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0'R,D1AT,#$-M"TA$"

+ormationof a C2 bondThe shae of an !3 "#$i%&l


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0'R,D1AT,#$-"TA$"

+ormationof a C2 bondThe shae of an !3 "#$i%&l


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0'R,D1AT,#$- T" %TR.CT.R" #+ "T"$"("T0*"$")/

!2 HYBRIDZATION

A process !or obtaining sp2-hybridized carbon atoms


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0'R,D1AT,#$- T" %TR.CT.R" #+ "T"$" ("T0*"$")/!2 HYBRIDZATION


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0'R,D1AT,#$- T" %TR.CT.R" #+ "T"$"("T0*"$")/!2 HYBRIDZATION


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0'R,D1AT,#$- T" %TR.CT.R" #+ A*30$"%(AC"T0*"$")/

! HYBRIDZATION

A rocess for obtaining !'()$#i*i+e* $"-&%".


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Chater 2 !olari4ation-,ntermolec&lar +orces

PolariBation i$ a c&an.e in electron #i$tri'"tion a$ a re$!on$e to

c&an.e in electronic nat"re o% t&e $"rro"n#in.$ PolariBa'ilit i$ t&e ten#enc to "n#er.o !olariBation

Polar reaction$ occ"r 'et*een re.ion$ o% &i.& electron #en$it an#re.ion$ o% lo* electron #en$it


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Chapter 1 Chemical Bond

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