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General Organic chemistry
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> TRODUCTION TO GENERAL ORGANIC CHEMISTRY LifINTRODUCTION © Organic chemistry is the chemistry discipline that is concerned with the study of compounds containing carbon that is chemically bonded to hydrogen. Organic chemistry encompasses the synthesis, identification, modeling, and chemical reactions of such compounds. = The range of chemical compounds studied in organic chemistry include hydrocarbons (compounds containing only carbon and hydrogen), carbons containing other elements, especially oxygen, nitrogen, sulphur, phosphorus and the certainly halogens. = The following is an example of an organic molecule Methane(CH,). line-angle structural formula shows four ~ hydrogen single bonds (o, im black), and the typical of tetrahedral molecules, with ~109° interior bond angles.)CLASSIFICATION OF ORGANIC MOLECULE ORGANIC COMPOUNDS are of two typest ALIPHATIC COMPOUNDS: open chain compounds. CLOSED CHAIN COMPOUNDS: closed chain ‘compounds. These are again classified into two typen HETEROCYCLIC COMPOUNDS: ring skeleton of compounde containing carbon tome along with sjome of other elements, (HOMOCYCLIC COMPOUNDS: ring skeleton of compouncle containing only carbon stome. These are of two types: e Alicyclic compounds: these compounde have resemblance in properties with aliphatic compound, Aromatic compounds: compound containing at least one benzene ring and having elternating double bonds within the ring. They’ have agreesble odor. These are further divided into two parts Benezoid : carbocyelic aromatic. + Non-Benezold: heterocyclic aromatic. (es st we eo omen)STRUCTURAL REPRESENTATION OF ORGANIC MOLECULE — = ORGANIC MOLECULES can be represented in the fallowing ways: > Complete structural formula: A structural formula in which two electron covalent bond is depicted by a dash is called complete structural formula. % Condensed structural formula: The structural formula obtained after deleting some or all of the covalent bonds and by indicating the number of identical groups attached to an atom by a subscript. The structural formula so obtained is ealled condensed structural forraula > Bond line structural formula: The structural formula obtained by representing carbon-carbon bond by zigzag lines and not highlighting the earbon and hydrogen atom is Inown as bond line structural formula, “aN encn.o1 Pentane i iad Fully Levicstniture Condensed condensed samnetaral rms seta orm oberon Am‘COMMON FUNCTIONAL GROUPS IN ORGANIC COMPOUNDS eras m Ps iia cts) i z UccE A Functional group may be cuettstaieshon defined as an atom or group of atoms which largely determines é Orman cer the properties of an organic meinane compound Sone on x “ oot ‘Aeeiono) eee The family of carbosylie acids contains a carboxyl (COOH. 1 ‘agtny etanoate functional group. Acetic acid, shown above, is an example.HOMOLOGOUS SERIES: A homologous series may be defined as a series of similarly stituted compounds in which the ‘members possess the same functional roup and have similar chemical characteristics and the two consecutive members differ in their molecular formula by- CH; The above diagramis the homologous series of alkenes while the diagram below portrays the homologous seties of the ikanes.CLEAVAGE OF COVALENT BONDS © Organic reactions involve brealdng of bonds in the 2eacting molecules and formation of new bonds to give rise to product molecules. The breaking of bonds can take place in two weys- a HOMOLYTIC CLEAVAGE: When the bonding electrons are equally divided into the atoms of & bond resulting in the formation of free radicals are known as homolytic cleavage cet + Cl hy b, HETEROLYTIC CLEAVAGE; When the bonding electron pair goes to the more electronegative atom of a covalent bond resulting into the formation of positively and negatively charged species are known as heterclytie cleavage. eterclytic bond cleavageREACTION INTERMEDIATES REACTION INTERMEDIATES are generally charged or neutral but elactron deficient unstable specien ‘which are formed from the cleavage of bonds during chemical reactions, They are az the following: > Fre alt i Have one odd clectron as itis formed due to homolytic cleavage. H ii Para-magnetic in naturedue to the presence of unpaired electrons. I ‘ H—C- il, Have both spond sps hybritization ] iv, Mostly undergoes iyperconjugation. H Stability of free radicals ip ae the following: radical ily increases In the order methyl < primary < secondary catecon 6 i Positively charged carbocation having @ valance electrons due to the oe~ i Ils sp2 hybridized and has # ioneular planner structure with bond angle 120°= TH thas vacant p orbital which is perpendicalar to the plane ,t0 it acto as a lewis acid. Iv. Stability of the carbocation is as the fllowing: ‘These ure op3 hybridized , negatively charged trivalent carbon Hos one pair of non-bonded electrons, Sil, Tehas a tetrahedral shape with bond angle 105 © 96°, so it has pyramidal shape jv, Stability of carbanion is ao the following: be he 4ATTACKING SPECIES i > NUCLEOPHILE: Nucleophiles are electron donating species. They are of two types: ‘+ Neutral nucleophile; They have non-honded donatable electrons, Tana Nac + Changed nucleophile: These have less no of electrons dlue to vacant fotitai, 0, Ny, RN, RH RGN ROH, COOH, SH, and PR yaroxide fon ae mcloopilo ° oe id Charged Nucleophier RO, "Nig RN, RN HS RS, REET," 1 F708", OH, Roo} ¥ ELECTROPHILE: Electrophiles are positively charged or electron deficient neutral species which can accept a pai of electrons in its vacant site, These are cleetron loving: speciesELECTRONIC EFFECTS Displacement of electrons + Temporary effect - Hyperconjugation * Permanent effect - Inductive effect & Resonance CL CHL CHL INDUCTIVE EFFECT G_ Only seen in sigma bonds. a G1 Te depends upon distance. een in ground state of a molecule Itis of two types sLeffect = Leffect 0 parta pstive charge ‘ patal negative charge 5 logs paral postive charge than s+ gk a $ ClagtC4o4i > 1ImGe Ceoet> a ‘ paral negative charge (seas partial postiveELECTRONIC EFFECTS / Displacement of electrons + Temporary effect - Hyperconjugation * Permanent effect - Inductive effect & Resonance CHL CL CPL INDUCTIVE EFFEC: (Only seen in sigma bonds. — - - - . s PL Fh FL _Y OTe depends upon distance. ‘cen in ground state of a molecule, It is of two types +L effect effect 1 partial postive charge ‘partial negative charge 9 loss paral postive charge than 3+ ae 99 HO Es 1 hl ClagtC44 > HIAGe CeOe> ge Coe a cr a {pata negative enarge leas pail postive charge than 5-RESONANCE : Teoceurs in conjugate system ie. sigma & pi system. Here electron release occurs via the pi bond. Here we see double electron transfer. Itis of two types yvooo -Reffect : Eg: resonance of nitrobenzeneYPERCONJUGATION. _Itis known as no bond resonance. | Stability depends on the availability of the no of al irogen (more alpha hydrogen, more stability)HYBRIDIZATION OF ORGANIC COMPOUNDS ==» The phenomenon of intermixing of orbitals of the same atom having slightly different energies to form new orbitals, ‘which have identical shapes and equivalent energies is known as hybridization, Hybridization is classified into six types sp: Twocqialent orbits formed de toinenixing of one 4 Scone p orbital are ealled sp hybrid orbitals and the i Wynne pte Haat = sp2; Three equivalent orbitals formed due to intermising of ones & two p orbital are called spa hybrid orbitals and the phenomenon is known as sp2-hybridization. Fg: Ethene© 9p3: Four equivalent orbitals formed due to intermixing of one ‘.& three p orbital are called sps hybrid orbitals and the phenomenon is known as sps-hybridization, Eg: Ethane © Sp3d_ Five equivalent orbitals formed due to intermixing of one orbital and one d orbital are called spsd hybrid ‘orbitals and the phenomenon is known as sps4-hybridization, Eg: PCs ‘Sp3d2; Six equivalent orbitals formed due to intermixing oF futhiepobial and to otal areal pada hybrid orbital andthe Phenomenon i own as spade-hyonidizaton Ep S, © Sp3d3:Seven equivalent orbitals formed due to intermixing of one three p orbital and three d orbitals are called spsds hybrid orbitals and the phenomenon is known as spsds-hybridization, Eg: IFy© sp3: Four equivalent orbitals formed due to intermixing of one ‘.& three p orbital are called sp hybrid orbitals and the phenomenon is known as sps-hybridization, Eg: Ethane © Sp3d_ Five equivalent orbitals formed due to intermixing of one orbital and one d orbital are called spsd hybrid ‘orbitals and the phenomenon is known as sps4-hybridization, Eg: PCs ‘Sp3d2; Six equivalent orbitals formed due to intermixing oF futhiepobial and to otal recalled pada hybrid orbital andthe Phenomenon i own a spsd2-hybnidzaton Ep S, © Sp3d3:Seven equivalent orbitals formed due to intermixing of one ‘three p orbital and three d orbitals are called spsds hybrid orbitals and the phenomenon is known as spsds-hybridization, Eg: IFy
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