i Chapter 2- Introduction to Organic Chemistry Organic Chemistry Chapter 2 INTRODUCTION TO ORGANIC CHEMISTRY ay ‘Organic chemistry is the chemistry of carbon compounds. But why. a separate study on carbon? Why is carbon special? What is it that sets carbon apart from all other elements in the periodic table? Carbon is just one of the 118 elements in the periodic table and not ‘one of the most abundant elements within the earth’s crust. The lithosphere is only 0.032% carbon by weight. In part, at least, the answer seems to be that: there are so very many compounds of carbon and their molecules can be so large and complex. Objectives: At the end of this chapter, the student should be able to: 1. recognize the existence of a great number of organic compounds; 2. explain the tremendous diversity in the structure of organic compounds; 3, compare and contrast properties of organic from inorganic compounds; classify types of structural isomerisms; identify functional groups and classify organic compounds; write organic formulas in different structure representations; and . classify types of organic reactions. CARBON COMPOUNDS Pee x ‘The study of carbon compounds was separated from compounds of all the other elements of the periodic table. Bettelheim, et al. (2004) pointed out four reasons why special attention is paid to carbon: 1. The first reason is largely historical, In the early days of chemistry, scientists thought that organic compounds were those produced by living organisms, and inorganic compounds were those found in rocks and other nonliving matter. At that time, they believed that a ‘vital force” possessed only by living organisms, was necessary to produce organic compounds. $ ‘Ma. Lourdes C. Alvarez College of Science, UBPChapter 2- Introduction to Organic Chemistry | 30 Organic Chemistry 2. A second reason for the study of carbon compounds as a separate discipline is'the ehcer number of organic compaunds.'Chemists have discovered or made more than 10 million of them and an estimated 10,000 new ones each year. i 3. A third reacon- and one particularly important for those who plan to study bicchemistry- is that carbohydrates, lipids, proteins, enzymes, nucleic ecids, hormones, vitamins, and clsioct ell other important chemicals in living systems are orgenic compounds. 4. One final point about organic compounds is that th differ from inorganic compounds in many of theee differences stem from the fact that bending in organic compounds is almost entirely covalent, while most inorganic compounds have ionic bonds generally properties.’ Most of ‘SOURCES OF ORGANIC COMPOUNDS Chemists obtoin organic compounds in prificipal ways: isolation from nature and synthesis in the labs Isolation fer ‘The principal natural sour plants, animals, natural gas, petroleum, and oil shale dict i plants and animals and even isms make’ thousands of organic compounds by a process called biosynthesis.” Living organisms ore scid to be chemical Zctories, One way to get organic compounds is to extract them from ti.ose biological sources. Synthesis in the Laboratory Organic chemists have sought to develop more ways to make the same compounds found in nature. In recent years, methods have become so otlvariced that there are only few organic compounds that cannot be synthesized in the laboratory. Compounds made in the laboratory are identical to those found in nature. However, orgenic chemists have not been satisfied with just duplicating nature’s compounds. They have’ also synthesized compounds riot found in Hatbre. In fact the nisjority of the more than ten million) Enown organie compounds eze purely synthetic and 4b not exist im living organisms. 7 Ma, Lourdes @. Alvarez Celteze of Science, UEPChapter 2- Introduction to Organic Chemistry Organic Chemistry o Self Assessment Activity (SAA) 2.1 °F Direction: Name the two principal ways of obtaini i gee ‘principal ways of obtaining organic 3 NATURE OF ORGANIC COMPOUNDS It is said that the number of organic compounds has been estimated recently to be around 40 million and still growing every year. This is several times the number of inorganic compounds, The vecurrence of a large number of organic compounds i due to the following reasons: 1. Carbon can form four bonds with other carbon atoms as well as with other atoms. Keleulé (Germany) and Couper (Scotland) were the first to recognize that carbon is tetravalent- it can form four bonds, not only with other atoms (chiefly H, but also F, Cl, Br, 1, O, N, S, P & many Others) but also with other carbon atoms. Carbon atoms sat form very strong covalent bonds with each other. It cap attach themselves to one another to an extent not possible for atoms. of any other element. 2, Carbon atoms can link with each other to form linear, pranched or cyclic chains. Carbon atoms can form chains thousands of atoms long, oF rings of all sizes; the rings and chains can have branches and cross- links, A four carbon atom can be linked to one ‘another in a number of ways: e7o-c-c c=He-¢ I c linear branched Tlement carbon forms ‘more com pounds than the entire ‘con pound 95 alte elements in the periodic table pul together.Chapter 2- Introduction to Organic Chemistry | 32 ‘Organic Chemistry 3. | Carbon has the ability to form single, double and triple bonds. j Single bond CEG c=0 cen Doublebond C=C c=0 O=N Triple bond cc c#P CaN ‘The Single bond is the longest and weakest bond while the triple ond is the shortest and strongest bond. Double bond is intermediate organic compound between the two bonds. methane conn Ny 4, Organic molecules exhibit isomerism. i eee Isomers (Greek: isos, equal; meros, part) are aiteset {arin compounds that have the same molecular formula. This difference * compa structure gives rise to a difference in properties. ¢ SAA 22 Car6on forms strong covalent Bonds? Why are the compounds of carbon cova bonds. What are covalent (ont rather than ionic? ji SAA 23 °F pivection: Classify the following as branched chain, unbranched | chain, cyctte chain, multiple bonded, heterocyclic: He _ BOSCH Hy CHy-E-CHy‘To answer SAA 23, recall that carbon can bond to form open-chain types can also have (unbranched) compounds or eyelle (ring) compounds. Both or multiple ‘branches of carton atoms, Carbon can also be bonded using single bond bonds (double or triple}. Cyclic compounds having at least one atom in the ring other ‘than C and Ht (@ heteroatom) are called heterocyeties. You may have more than 1 answer for each item. Isomers are compounds that have the same parts but are not ; the same. The two general types of isomerisms are structural f isomerism and stereoisomerism. Structural Isomerism Structural isomers contain the same numbers of the same kinds of atoms, but the atoms are attached to one another in different ways. Atoms are arranged in a completely different order. Structural isomers are also called constitutional isomers. ‘Types of Structural Isomerism 1. Skeletal or Chain Isomerism These isomers arise because of the possibility of branching in carbon chains. For example, in butane (CsHio), ‘the carbon atoms may lie in a “straight chain* or in a ‘branched chain. cH, i CH,CHCHLCH cH.CHCH ‘Mo. Laurles C. Alvarez Collegeof Science, UEPieee Chapter 2- Introduction to Organi Chemiatry | 34 Organie Chemistry Another T example of skeletal isomerism is shown below: CHa=CHCHaCH2CH:CHs CHa=CHCH,CHCHs CH ‘The structures have the same molecular formula el ay Hate the same functional group (c-0) and the ion of functional iffer in th structure of the carbon. aden Oe eae 2. Positional Isomerism _In positional isomerism, the basic carbon skeleton remains the same but the groups are moved on that skeleton. ‘The two structures have the same molecular CH. sCH2CH2Br formula (CoHrBr). Br is on the end of the cllagHics chain but in another structure its attached i on the middle carbon, ‘Another example of positional isomerism is shown on the structures below. They have the same functional group and the same overall structure of molecular chain but differ in the position of functional group. ‘The two structures above have the same CH= CCH2CH2CH2CHs oiecutar formula (Cel). They have the same functional group (CC) and both have linear chains but the triple bonds are in different position. (CH3CH2C=CCH2CHs 3. Functional Isomerism ‘The functional isomers contain different functional groups. They belong to different families of compounds. For example, two structural formulas can be derived from the molecular formula CzH.0. One is an alcohol (R-OH) while the other one is ether (R-O-R). Ethyl alcohol dimethyl ether liquid, bp 78.5" gas, bp -24°C ‘Ma Lourdes C: Alvarez. College of Science, UBP. iii caSonor eneesaesinantannennesnermnnererset steseeseonomneneomepepemenennieennmenvemnem 35 Chapter 2- introduction to Organie Chemistry ‘Organic Chomsist7 Stereisomeriam aa Stereoisomers (Greek: stereos, solid) have the same molecular seunnity formulas but differ from each other in their three” sional structures (orientation oftheir atoms in space). "BE% O° two main types of sterecisomerisams: geometric (cis-trans) and optical. fi SAA 2.4 *" Direction: Tell which pairs are structural isomers. Uf the pair | exhibits structural isomerism, classify them as steletab ‘positional or functional isomers. 1 CHsCHa (CHsCH2CH2CHs ‘organic and (CH3CHa Se ric cont 2 ° g oon CHSCH.C-H cHs-b-cHs ‘aigfer in res ties ie because (CH3CH2CH2CH2CH20H (CHsCH2CH2CHCHs they be en struc- tures. 4. (CHsCH2CHiCHs (CHsCHaCHs 6. (CHsCH2CH2CHs CHsCHCHs Hs COMPARISON OF ORGANIC AND INORGANIC COMPOUNDS 1. Organic compounds are formed by covalent linkage, while inorganic compounds are joined by electrovalent or ionic bonds. 2, Organic compounds may be gases, liquids or solids with low melting points (less than 360°C). Most inorganic compounds are solids with high melting point. 3. Most organic compounds are insoluble in water, while many inorganic compounds are soluble in water. 4, Most organic compounds are soluble in organic solvents such as diethyl ether, toluene, dichloromethane, chloroform, and benzene, Almost all inorganic compounds are insoluble. in organic solvents. ‘Me. Lourdes © Alvarez College of Science, UEPChapter 2- Introduction to Organic Chemistry | 36 ‘Organic Chemistry 5. Organi Sive carbon aa pounds burn readily, some spontaneously to Inorganic compe nat? Wate and in some cases other products. pounds are usually incombustible. 7 orenks compounds are less stable toward heat. linkage of atom: compounds do not fonize and properties are due to SH cae Molecules: argaie compounds ionize’ readily lution, a _8: Aqueous solutions of organic compounds do not conduct tricity while that of inorganic compounds conduct electricity. 9. Reactions of organic compounds are usually slow while reactions of inorganic compounds are often very fast. SAA2.5 “Why are reactions of inorganic compounds faster than that of organic compounds? CLASSES OF ORGANIC COMPOUNDS S ‘Organic compounds can be classified into two groups: hydrocarbon and those with heteroatoms. Hydrocarbons contain only ments other than carbon and hydrogen hydrogen and carbon. Ele: found in organic compounds are called heteroatoms, ORGANIC COMPOUNDS “Hy arbons with Heteroatoms Fes, aliphatics aromatics alkaiies alkenes alkynes cyclic analogs with owen with sulfur with Halogen seis slides epee ee ceo oor ian fs , fant a, Figure 1.2, The different classes of organic compounds Ma. Lourdes C. Alvarez College af Sclenoe, UEP aChapter 2- Introduction to Organic Chemistry: 37 Organic ‘Chemistry L Identify 3 classes of organic compounds that contain nitrogen. a b. c : 2, On the basis of structure, into two main classes. What are these two classes? fiydrocarbons are divided {FUNCTIONAL GROUPS chee ie ee Te structural features that allow us to class Functional group: ands together by reactivity. A functi osed of an atom or Brot onal group is a part of a up of atoms having & ivity. They are sites of chemical reaction. ‘al group behaves in approximately the hich it is @ part. Functional grouP also pounds. With the exception compo larger molecule; it is comp characteristic chemical react! Chemically, a given function same way in all molecules of w serves as a basis for naming organic com! of alkanes, each class cont "A large part of organic chemistry is just functional groups. Therefore, we do not ave to study all the more than 10 million organic compounds. Instead, we need to identify only a few functional groups and then study general properties and characteristics of each. G SAA27 ‘ What is a functional group? Describe if im four short statements: College of Science, UEP Ma Lourdes ©. AlvarezChapter 2- Introduction to Organic Chemistry | 38 ‘Organic Chemistry Class/Com; Romie Functional ‘Simple example Name Gro ding ‘Alkene v vP ie = (double bona) ‘One CHAS eS cent / Propene ; Alkyne CH,C=cH {triple bond) —c=C— a ! Arene/aromatic sor ne {aromatic ring) ar S \ CH3CH2I : —c-x . none Alkyl halide 7 fedoatkiana X =F, Cl Br Ae fi ‘Aryl halide ae a ex chiorobenzene X= F,CLBrt Ves CH,CH,OH Alcohol ay Ethanol ae on 0-H a a pctlorophenat f CHsCH, OCH;CHs —c-0-C— eee th Ether 7 \ Evhoxyethane oe (diethyl ether) H ° ‘Aldehyde ono cH O—H st Je! Ethanal “ (acetaldehyde) ‘Ma. Lourdes C, Alvarez College of Science, UEP‘Chapter 2- Introduction to Organic Chemistry | 39 ‘Organic Chemistry Class/Compound Fonctloual Type ; Simple example Name Ending Ketone 9 -one CH,—C—CHy mn 2-Propanone (acetone) Carboxylic aci 9 eros ach ! I -oic acid —C-O-H — CH,CH,CH.C—OH Bu anvie acid ° Ser cH é —OCH,CHs ~oate Eyl ethanoate (il acetate) e i yl halide Acid halide [ 5 5 —¢-x! OH;CH.C—Cl Propaneyl chloride see” Pk Acid anhydride | ON wee —e- ay. eaardide Sanne CaiteO3 et Acetic anhydride ° 9 Amide cheat cuted te, -amide Bthanamide CHsC=N a Nitrile —-CmN Ethanenitrile -nitrile {gcetonitrile) CHCHNHe eres ae Ethylamine Nitro CHsCH:NOz wiehs Nitroethane CHy—S— CHs Sulfide Dimethyl eulfide sulfide a Sulfoxide Ci —s—cH, sulfoxide Dimethy! eulfoxide ‘Ma Lourdes C. Awaren College of Science, UEP‘Chapter 2- Introduction to Organic Chemistry | 40 Organic Chemistry pe Functional ~~ Simple example Name Type =. 22° _Grow Sr anny nee a Sulfone past cy —$EcHs sulfone o o Dimethyl sulfone Thiol CHCH, SH thiol ethaneth ol cad chub Organometallic Matter one M = mel jo SAA 28 . ac Girection: Identify the class of compound m the following Rh ne) Kane Ma. Lourdes C. Alvarez College of Science, UEPChay ‘ter 2- Introduction to Organic Chemistry | 41 Organic Chemistry | onal group. following formulas: ‘TYPES OF FORMULA vy pais General Formula ‘This formula represents an entire series of compounds. Ex. CaHze2 alkanes CsHa2 alkynes R-OH alcohols Molecular Formula This formula gives the actual number of atoms of the constituent elements in the molecule. Ex. C2Ha acetylene CHO ethanol Simplest or Empirical Formula ‘This formula gives the simplest ratio of the atoms in the molecule. Ex. Benzene (CeHe) hasa simplest formula of CH Ghucose ( CeH120s) has a simplest formula of CH20 (ote: Some compounds may have similar empirical and molecular formulas.) Me. Lourdes C Alvarez College of Science, UEPChi ‘apter 2- Introduction to Organic Chemistry | 42 Organic Chemistry tra Structural Formula/Dash Structural Formula Structural foi mula shows th of atoms i fe arrangement of at s in the molecule. All bonds of the Scare et Ex. if HH wee ong a oa on a! WN tN HH { Hi. ethanol toluene acetic acid note: when unshared electrons are included, the later are also called Lewis (electron-dot) structures Condensed Structural Formula This formula represents structural formula ‘n a simpler wAy- ‘Arrangement of atoms or group of atoms s shown but te structure does not show all the bonds of the atoms in the molecule. Ex. Ethanol as shown above can be written as CH3-CH2-OH or (CH3CH20H Acetic acid can be written as (CHs-COOH or CHsCOOH Structures can also be written in yet another condensed form. In this representation, all hydrogen’s and branched groups are written immediately after the carbon atom to which they are attached. Similar units are also combined. This formula is sometimes referred to as abbreviated condensed formula. Ex. H Teobutane CHs- ¢-CHs is written as CHsCH(CHs)2 CHa n-pentane CHsCH2CHaCH2CHs is written as ‘ CH3(CHa)sCHs Line-Angle Formula or Bond-line Formule This is an abbreviated way to draw structural formulas in which each angle represents a carbon atom and each line represents a bond. A line ending in space represents & ~CHs group. Chemists preferred this structure. This is less time- ernsuming and the resultant drawing is not cluttered. Other Chemists call this as line-bond drawing or skeletal diagram. ‘The rules for this shorthand are simple: ‘a. Carbon atoms are not usually shown. Instead, a carbon atom is implicitly assumed to be at each intersection of two lines Ma Lourdes C. Aluares College of Science, UEPChapter 2- Introduction to Organic Chemistry Organic Chemistry 2 7. Write the different formula representations of the following organi¢ compounds. Molecular Empirical Structural Condensed/abbreviated Line-angle condensed e reo ee ar eel Seo. HH HH 2 et - 3. (CH9.CHCH:CH: | : Ag Oo oe Ss. Ma Lawties © Abares Callege of Ssience, UEP