RGANIC CHEMISTRY 1 CHM456

Paclitaxel (Taxol) anticancer co !o"n# i$olate# %ro t&e 'ar( o% t&e !aci%ic )e* tree

MOHD FAZLI MOHAMMAT @ M YAHYA A513 OLD ENGINEERING BLOCK, UiTM Tel: 55211354

Carbon Compounds and Chemical Bonds 1.1 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

Co"r$e +"tline

Introduction to Organic Reactions 2.1 'eactions and mechanisms: substitution$ elimination$ addition and rearrangement 2.2 !omol"sis and heterol"sis of covalent bonds$ homogenic and heterogenic of bonds 2.3 %cid(base reactions: 2.2.1 Carbocations and carbanions 2.2.2 Strengths of acids and bases: )a and 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$meso compound$ specific rotation 3.2 &olecules .ith more than one stereocenter

Alkanes and cycloalkanes 4.1 Structure and /omenclature 4.2 4.3 4.4 4. 4.2 Ph"sical Properties 0ond 'otation and Conformational %nal"sis of 0utane Stabilit" of C"cloal1anes: 'ing Strain and Conformation of C"clohe-ane S"nthesis of %l1anes: !"drogenation of %l1enes and %l1"nes$ 'eduction of %l1"l !alide$ %l1"lation of terminal %l1"nes 'eaction of %l1anes .ith !alogens: Chlorination of &ethane

Alkyl Halides .1 .2 Structure and Ph"sical Properties of %l1"l !alides /ucleophilic Substitution 'eactions .2.1 /ucleophiles and 3eaving 4roups .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 *limination 'eactions of %l1"l !alides .3.1 *2 'eactions .3.2 *1 'eactions Substitution versus *limination

Co"r$e +"tline

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Alkenes and Alkynes 2.1 %l1enes: /omenclature$ Structure and Ph"sical Properties 2.2 'eactions and &echanisms 2.2.1 S"nthesis of %l1enes via *limination 'eactions: 5eh"drohalogenation$ 5eh"dration$ 5ebromination 2.2.2 %ddition 'eactions : and &ar1ovni1ov6s and %nti&ar1ovni1ov6s 'ule 2.3 %l1"nes: /omenclature$ Structure and Ph"sical Properties 2.4 'eactions and &echanisms 2.4.1 %ddition$ !"dration$ ,-idation and 'eduction Alcohols and Ethers 7.1 7.2 7.3 7.4 7. Structure$ /omenclature and Ph"sical Properties S"nthesis of %lcohols from %l1enes 'eactions of %lcohols$ %lcohols as %cids8 Conversion to %l1"l !alides8 ,-idation to Carbon"l Compounds S"nthesis and 'eactions of *thers Phenols: Structure and /omenclature8 S"nthesis and 'eactions

Benzene and Aromaticity 9.1 9.2 9.3 Introduction: 0en#ene$ /omenclature8 Structure and Stabilit"8 !uc1el6s 'ule ,ther %romatic Compounds and !eteroc"clic %romatic Compounds 'eactions of %romatic Compounds 9.3.1 *lectrophilic %romatic Substitution 9.3.2 !alogenation8 /itration and Sulfonation 9.3.3 Friedel(Craft6s %l1"lation and %c"lation

Teaching Methodology ,ect"re$ an# la'orator) $e$$ion$ Assessment A$$i.n ent$ / 101 Te$t$ / 201 ,a'orator) re!ort$ / 301 4inal exa ination / 401 Recommended Text Solo on$ an# 4r)&le5 6t& E#ition5 +r.anic C&e i$tr)5 7ile) 3008 Morri$on 9o)#5 +r.anic C&e i$tr) McM"rra): ;5 +r.anic C&e i$tr)

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

Food
Fertilizer, pesticides, preservatives, additives

Materials
Polymers, coatings, adhesives

Drugs
Aspirin, Viagra, Neuro en

!he entire modern "orld

Petrochemicals, environmental chemistry, etc

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a.ic Car'on ato

: Difference between organic and inorganic is C-atom ability to form very long chain (catenation)
; Inor.anic co !o"n# *ill 'eco e "n$ta'le a%ter *it& 13 or ore ato $5 ; C=ato $ a'ilit) to %or >er) $tron. co>alent 'on#

C A!T"R #$" %tr&ct&re and 'onding

Cha(ter ) - %tr&ct&re and 'onding

"*"CTR#$ C#$+,-.RAT,#$ Electron$ re$i#e aro"n# t&e n"cle"$ in #i$crete ener.) le>el$5 T&e$e ener.) $&ell$ contain or'ital$ = a at&e atical !ro'a'ilit) t&at an electron *ill exi$t in t&at $!ace5 +r'ital$ are #e$cri'e# ') ?"ant" ec&anic$ in #i$tinct $&a!e$5 S or'ital$ are $!&erical an# ! or'ital$ are $&a!e# li(e #" ''ell$5 A"%'a" Princi!le = t&e lo*e$t ener.) or'ital %ill$ "! %ir$t Pa"li Excl"$ion Princi!le = onl) t*o electron$ can occ"!) an or'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.) are a>aila'le t&e) are %ille# *it& one electron o% !arallel $!in "ntil all are &al% %ille#5 +nl) t&en *ill electron$ 'e !aire# "!5 T&i$ i$ i !ortant in %illin. t&e t&ree ! or'ital$ Aalence electron$ are t&o$e in t&e o"ter o$t ener.) $&ell o%

Cha(ter ) - 'onding and %tr&ct&re

Ionic 9on#$ = Ato $ &el# to.et&er ') electro$tatic attraction (ion$)5 Co>alent 9on#$ = Ato $ $&are electron$ 'et*een t&e t&an ionic 'on#$5 = "c& $tron.er

Car'on (1$33$33!3) *o"l# &a>e to .ain or lo$e 4 electron$ to ac&ie>e a %ille# $&ell an# i$ t&ere%ore not ea$il) ioniBe#5 Car'on %or $ co>alent 'on#$ rat&er t&an ionic 'on#$5 Molec"le = a collection o% ato $ &el# to.et&er ') co>alent 'on#$5 ,e*i$ Str"ct"re$ = re!re$ent t&e >alence electron$ aro"n# t&e ato ') #ot$5 Co>alent 'on#$ are $&o*n *it& t&e t*o electron C#ot$D $&are# 'et*een t&e ato $5 Ee("lF Str"ct"re$ = Eac& co>alent 'on# i$ re!re$ente# ') a $in.le line in#icatin. t*o $&are# electron$5

Cha(ter ) - 'onding and %tr&ct&re

Cha(ter ) - 'onding and %tr&ct&re

Three-Dimensional +orm&las

Cha(ter ) - 'onding and %tr&ct&re

Cha(ter ) - 'onding and %tr&ct&re

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 $ / e5.5 car'onate

Cha(ter ) - 'onding and %tr&ct&re

0'R,D1AT,#$ T " %TR.CT.R" #+ M"T A$" A$D "T A$"/ !3 HYBRIDZATION Orbital hybridization: A mathematical approach that in ol es the combining of individual .ave functions for s and p orbitals to obtain .ave functions for ne. orbitals G hybrid atomic orbitals

Cha(ter ) - 'onding and %tr&ct&re

0'R,D1AT,#$

Cha(ter ) - 'onding and %tr&ct&re

0'R,D1AT,#$-M"T A$" +ormation of a C2 bond The sha(e of an !3 "#$i%&l

Cha(ter ) - 'onding and %tr&ct&re

0'R,D1AT,#$-"T A$" +ormation of a C2 bond The sha(e of an !3 "#$i%&l

Cha(ter ) - 'onding and %tr&ct&re

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

A process !or obtaining sp2-hybridized carbon atoms

Cha(ter ) - 'onding and %tr&ct&re

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

Cha(ter ) - 'onding and %tr&ct&re

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

Cha(ter ) - 'onding and %tr&ct&re

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

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

Cha(ter ) - 'onding and %tr&ct&re

Cha(ter ) 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)