[ORGANIC CHEMISTRY (MODULE 2)| The Periodic Table: as seen by an organic chemist. j who cares a eee ciaUNIT1 It is a study of the chemistry of organic molecules Organic molecules are molecules that contain q carbon. WHY CARBON? Carbon has 4 valence electrons and thus always o(, a forms 4 covalent bonds with other atoms: « Carbon bonds with other carbon atoms to make single, double or triple covalent bonds, Long chain, branched or ring structures can thus form. * Carbon also forms bonds with other atoms like H, O, N, febce These properties of the carbon atom have resulted in over 10 million known organic compounds!SOME BASICS Organic compounds are grouped into separate families according to their physical and chemical properties. The family (homologous series) to which an organic compound belongs to is determined by the functional group in the organic molecule. an organic compound its characteristic chemical and physical properties. A family of organic compounds that can be represented by the same general formula and have the same functional group. H ‘unctional group Ho 4H Functional group 1 for alcohol I uot for carboxylic Hc Hcl co acid/ 1 4 4 methanol (a member of the ethanoic acid (a member of the Sleohel family) carboxylic acid family)REPRESENTING ORGANIC MOLECULES Below are some of the common ways you will see organic compounds represented: Type of formula Description Example General formula Describes a homologous series. alkane | coHane2 Molecular formula | Only indicate the actual number of each type of atom =| Propane CH, in the molecule. (of a specific ome organic compound) Condensed Show how the atoms in the ‘structural formula | molecule are bonded but do Propane You will see this | not show all the bonds. Pane | CHsCH2CHs often between each atoms. ‘Structural formula | Show all the bonds in the This is used often | molecule and specify clearly land the easiest way Which atoms are bonded Propane to represent an organic reaction. together, = 1 x=r—9— rox I =—o—= xconsists of lines only. The lines represent the bonds and the cross sections and ends of the lines represent the C-atoms. Other atoms or alkyl groups will be indicated as in structural for- mula. Gives the best representation of the form of the molecule. Dark wedged lines Indicate bonds that come out of the plane of the page, normal lines are in the same plane as the page and the dotted lines go behind the plane of the page.Functional C,H,,.;OH Propan-1-ol 1-propanol Haloalkanes (Alkylhalides) T-chloro- propane ‘Aldehydes Propanal Propanone CnH2nO2 = Propanoic acidorganic compounds that contain only carbon and ai atoms There are 3 families of hydrocarbons: ALKANES A compound of carbon and hydrogen containing only carbon-carbon single bonds. ALKENES A compound of carbon and hydrogen that contains a carbon-carbon double bond. UT? THE HYDROCARBONS eee ALK YNES A compound of carbon and hydrogen that contains a carbon-carbon triple bond.Saturated hydrocarbons Coles M Ol Pleed Functional group C—C HYDROCARBONS: ALKANES The first 4 members of the alkanes: structural formula _ ball-and-stick model methane i / H-C-H 4 CHs U FP HH The ball-and-stick ethane Lot 4 models show that OH H-C—C-H we the molecules are a 4 4 i 3 actually three z dimensional and propane tt i ‘i i ’ not flat and straight CH ae ea : oe as the structural a HHH ‘ formula show: H HHH y) } butane eePient . cite EEE gy aici HH HHThe first 8 members of the alkane Note how the name of the alkanes a 1 CH, "methane aiding Ss always ends in ‘ane’. 2 C2Hs ethane oh The prefix in the name (highlighted in yellow alongside) is determined by the number of carbon atoms. 3. C3He propane a Also note how the molecular formula of each alkane (in blue) fits the general formula: CnHan+2 ‘butane 5 CsHig —eintane “ “hemane 6 CoH 7 Cryo heptane *HYDROCARBONS: blir General formula CnHan ALKENES Functional group C=C The first 5 members of the alkenes: )jo7f. | ALKENE | CARBON [Molecular] structural | [here is no alkene with only 4 NUMBER | FORMULA FTES carbon atom (methene). This is ETHENE 2 He | aw because,as the functional group Ge indicates, there need to be at na least 2 carbon atoms ina PROPENE | 3 GH | HB molecule for the double bond to Gate exist. nA ALSO: BUTENE 4 cHe |e Not all the carbon bonds are (1-butene)| gree et double, there just needs to be ° " at least one double bond. PENTENE 5 Gio | yao ee AND: ({|-pentene) G-e-G-E-G-H_ | The 4 in the names (in orange 5 nae alongside) shows that, in this case, HEXENE 6 cea | 4 # # 4 4 4 | |the double bond is on the first [1-hexene) ¢=C-C-¢-C-C-H| carbon. See note over the page in HOUR RAA | this regard,MORE ON THE ALKENES (Just read through and understand. All this is already summarised in a separate note on naming organic compounds using the IUPAC rules We will still spend a whole lesson/s interacting with all the rules later) We will soon learn the IUPAC rules for naming organic compounds. We have already seen a few basic rules in action: (e.g. the name ending (suffix) depends on the homologous series: ‘ane’ for alkanes, ‘ene’ for alkenes; the prefix depends on the number of carbon atoms in the chain: 'meth' for 1 C, 'eth' for two carbons, etc.) In the case of alkenes (and other families yet to be learnt) the functional group can be in different positions within the chain and this needs to be indicated in the name. So, on the previous page, 1-pentene tells us that the double bond is on the first carbon. If we had 2-pentene this tells us that the double bond is on the second carbon The carbons in the chain are always numbered so as to give the functional group, in this case the double bond, the lowest possible number, That is why the carbons jare numbered from the left in the above examples. (They won't always be)HYDROCARBONS: [mm hydrocarbons ALKYNES General formula CnHan-2 eee Functional group C=C The first 5S members of the alkynes: Name _ Structural formula Con ed structural formula Ethyne H-C=C-H CoH2_ |eH-cx (CHCH) The z molecular Propyne | 7S =O-FOH C3H4 | cuec-cx; (CHCCHs)| formulas are H in blue and HH will always Butyne | H-C=C-¢- 6-H (CHECH2CHs) obey the 4-butyne| gs Cite [SO general (1-pentyn¢) H formula ror (etc.) Pentyne | H-C = C-C- C-C—H ioe oe CH-C-CH,-CH,-CH, CsHs 1-hexynd) ae a Hexyne |H— C= C-€- €~C— ¢ — Hl cHac-cu.-CH.-CH:- CH:Saturated compounds: Compounds with only single bonds between carbon atoms in their hydrocarbon chains. Unsaturated compounds: Compounds in which there are multiple bonds (double or triple bonds between carbon atoms in their hydrocarbon chains. Alkanes are therefore saturated. Alkenes and alkynes are unsaturated. TEST FOR SATURATED AND UNSATURATED COMPOUNDS ch the video ": turation test re the experiment is demonstrated cy hexane (saturated) and cyclohexene (unsaturated). \timmmidtmmmeniemmes OO ~ Add a few crops bromine water, which is or in fange-brown, to the compound to be tested as an unsaturated hycrocarton, Shake the sotution if the solution aiscolours immediately without having to put it in sunlight, then the solution is en unsaturated lyOrocarbon (an alkene or an alkyne) -If the orange. ah saree ‘rown colour does not disappear immediately, then the solution is a saturated hydrocarbon (an PTO} _—iThe bromine reacts with the unsaturated compound (in an addition reaction) which is why it discolours. The bromine does not react with the saturated compound (alkane) hence it remaing” browny-orange. We will learn more about these types of reactions later. | Homologous. ALKANES ALKENES ALKYNES Series UY General formula | CsHon+2 (CaHan CaHor2 Functional Single bond Double bond Triple bond Group between C between C between C atoms atoms atoms Nameends in | “ane’ ‘ene’ ‘yne’ Saturated / Saturated Unsaturated Unsaturated IY] Y PS unsaturated | compound compound compound R Vv Reactions Substitution, Addition Addition we will learn | Elimination these later combustioBASIC QUESTIONS: HYDROCARBONS: 1. State the homologous series that the following compounds belong to and give the IUPAC name of each. a) C3Hs b) CsHio c) CsHi2 d) C3Ha e) CsHis f) CsHs g) CsHia 2. Write down the molecular formulae for each of the following; a) ethene b) butane c) methane d) hexyne e) 2-octene f) pentane g) propyne h) 3-heptene i) 1-heptyne 3. Complete the molecular formula for the following compounds (the homologous series is stated): a) alkane CsH_ b) alkene C_Hio c) alkyne CsH_ d) alkene C3H_ e) alkane C_Hs f) alkyne C_Hia g) alkene CioH_ h) alkane CsH_ i) alkyne CzH_ 4, Give the structural formula and IUPAC name for each of the following compounds: a) CH3CHCH> b) CH3(CH2)3CH3 €) CH3CCH d) CH2CH2 @) CH3CHCHCH3 f) CHyCH2CCCH2CH,CHy eee eelunits COMPLEX HYDROCARBONS So far we have only looked at hydrocarbons with straight chains. In this unit we will see complex hydrocarbons where they will have branches. We will use the IUPAC rules to name these more complex organic compounds. E.g: The condensed structural formula of a branched hydrocarbon. | —_ parent (root) chain) + branches AM ok ed Mom = *See IUPAC naming | rules’ note —_— rules’ LWORKED EXAMPLE 1 ¢ functional group: = C single bonds = ane * longest chain =6C=hex * number carbons; circle branches - (must get lowest number) * name branches * two methyl branches = dimethyl * alphabetical order = ethyl before methy ¢ Final name stating name and position of branches before parent chain ® puncuation NB = hyphens, commas and no spaces. 3-ethyl-2,5-dimethylhexane NOTE: there are other options for a 6 carbon chain but it wouldn't change neti) However, don't try this as your longest chain as then we get a weird branch: numbering must be from R to L. If it was from L to R, then branches would be on 2,4and5. 3 for the ethyl branch is lower than 4.functional group: = C double bond = ene * longest chain (must contain functional group) =5C =pent * number carbons; functional group must get lowest number, not branches. Functional group on 2nd carbon, hence 2-pentene or pent-2-ene © circle and name branches © alphabetical order = ethyl before methyl ¢ Final name stating name and position of branches before parent chain * puncuation NB = hyphens, commas and | NOTE: | there are other options for a 5 carbon chain but it wouldn't change the final name. | numbering must be from R to L. If it was from L to R, then double bond would be | on 3rd carbon. It must get lowest number.WORKED EXAMPLE 3 ; tional group: = C double bond = ene * longest chain (must contain functional group) =4C it * number carbons; functional group must Hy get lowest number, not branches. Functional group on 1st carbon, hence 1-butene or but-1-ene © circle and name branches * 2 methyl branches = dimethy * Final name stating name and position of branches before parent chain * puncuation NB = hyphens, commas and 3,3-dimethyl-1-butene OR 3,3-dimethylbut-1-ene NO 2 there are other options for a 4 carbon chain but it wouldn't change the final name. TOTP YY PTF THTY TPP YY HPT TEA numbering must be from L to R. If it was from R to L, then double bond would be on 3rd carbon. It must get lowest number.WORKED EXAMPLE4 4) (((1) CH,CH,CHIC,H,)CH,CH,CH, This is a condensed strut its name if you draw out its str (alee CH ‘CICA, CH,CHIC, H,)CH,CH,CH, If you look at the structure of a straight chained alkane, you will notice that the carbons on the end have 3 hydrogens (CH3). The carbons in the middle have only 2 hydrogens (CH). This structure, however, has a and this indicates that there must be branches on this carbon. In this case there are 2 and they are indicated in brackets as (CH3)z2 which makes them both methyl. and this indicates that there is anotherPRACTISE BY NAMING THE FOLLOWNG COMPOUNDS: 1. CHy=CH, G “OY ee cyESTERS: QUESTIONS 1. Complete the following table: Alcohol Carboxyl acid Ester Molecular formula || methanol ‘ethanoic acid | ethanol methanoic acid | propanol methanoic acid 1 methanol propanoic acid | ‘propyT ethanoate ethyl butanoate pentyl pentanoate butyl octanoate 2. Draw the structural formula and give the IUPAC names for the TVO unbranched esters with the molecular formula CaHsO2 3. Draw the structural formulae and give the IUPAC name of a FUNCTIONAL isomer of the esters in Question 2. H oO iff 4 TM a 4. Give the IUPAC names of the following: a) HOW b) i | Ht I fl I | Ho H—C—O—C—G—H Cic) H q a HoH HOW : 4 H HH H H QO eau | ene ance CH tt O-CHy-CHy-CHy-CHp-CHyUNIT 6 APPLICATIONS OF ORGANIC CHEMISTRY 1. COMBUSTION OF FOSSIL FUELS Read through the section on fossil fuels in MODULE 2 Unit 6 (pg. 102, 103) of your textbook. The alkanes burn in oxygen (air) to form water, carbon dioxide and a huge amount of energy. These reactions are called combustion and are highly exothermic. (AH < 0) ¢ Because of this property alkanes are mainly used as fuels. ¢ If the alkanes burn in limited oxygen, carbon monoxide instead of carbon dioxide is formed. Alkane combustion reactions are very easy to write. We use molecular formula (in other organic reactions we have yet to study we will always use structural formula). The hardest part about writing the equations is balancing them (and this isn't even hard) Tanna alias GENERAL EQUATION FOR ALKANE COMBUSTION alkane + OAs the alkane hydrocarbon chain gets longer the balancing numbers in the combustion equation get bigger: The equation for the combustion of hexane (CsHi4) is given below. 2CeHi4 + 1902—» 12CO2 + 14H20 Alkane + oxygen — carbon dioxide + water + energy Follow these simple steps when balancing these combustion reactions: + Balance the carbon atoms first * Balance the hydrogen atoms second * Lastly balance the oxygen atoms: For the alkanes with an even number of carbons (CH¢, C4Hg, CsHi9, etc.) you will end up with an odd number of oxygens on the RHS. Because the LHS already has Oz, you would need a number and a half (e.g. 2,5) as a co-efficient (balancing number) number on the LHS. This is not allowed and easily overcome by doubling each of the co-efficients in the equation. Try this out for yourself - it is relatively easy. Eg: in the example above with hexane: Initially: there are 6 C's on LHS, hence put a 6 in front of the CO2 on RHS; there are 14 H's on LHS, hence put a 7 in front of the HO on RHS: CoHis + O2—~6CO2 + 7H20 Now there are 19 O's on RHS, since there are already 2 O's on LHS you would need 9,5 in front of the O2. This is not allowed so double co-efficients. 9,5 then becomes 19 and eqn will look like it does in the example top of page.Read through incomplete combustion reactions and Climate Change on pg. 104, Do UNIT 6, Activity 3, no. 1 and 2.Esterification is reaction in which an alcohol reacts: with a carboxylic acid to form an ester and water. assists in the removal of a molecule of REACTION heat must be applied water(H20) frow: the CONDITIONS acatalystis needed: reactants. concentrated sulphuric acid (H2SO,4) THE GENERAL EQUATION: ALCOHOL + CARBOXYLIC ACID —— ESTER ++ WATER examples: ethanol © + methanoic acid ——- ethyl methanoate + water methanol + ethanoic acid ——- methyl ethanoate + water propanol + pentanoic acid —- propyl pentaanoate + water Notice how the alcohol used determines the first part of the ester's name and the carboxylic acid used determines the second part of the ester's name Remember: the first part of ester is the carbon chain without the carbonyl gp while the second part of its name is the carbon chain with the carbonyl gp.The esterification examples on the previous page are word equations. If we write them as chemical equations then we ALWAYS use STRUCTURAL FORMULA to do so. (these structural formula could then get condensed if you are asked to use condensed structural formula) These equations are very easy to write, especially if you draw the functional groups of the alcohol and the carboxylic acid facing each other as shown below. To draw the structure of the ester that forms simply remove an O-H and an O atom from the reactants (H2O) and join what's left over together. Don't forget to write the H20 that is removed on the RHS as a product. Suppose we react propanoic acid and methanol: H—O, o + H H HH H HH The ester we make is called methyl propanoate See another example over the page!Do MODULE 2, UNIT 6 Activity 2, no. 1 and 2 (For 2.3, draw the structural formula first if you need to see it more clearly). ANOTHER EXAMPLE OF ESTERIFICATION: Acid + alcohol => ester + water. eg ethanoic acid + ethanol ethylethanoate + water H 9 HoH I I 4—t-d_off_H-o} c—C-H iF | HH H2S04 The water does not H ae HoH need to be written H-c~C-0—C—C-H *[H20 | witha structural H HH formula since Ut is coe ethyl group tnorgante- (ethyl ethanoate)ESTERIFICATION: QUESTIONS 1, Use (i) structural formulae and (ii) condensed structural formula to write down the equation for: (Write the IUPAC name of each organic compound underneath its formula) a) the reaction between ethanol and propanoic acid b) the reaction between methanol and ethanoic acid. c) the preparation of propyl pentanoate. d) the preparation of an ester containing 5 carbons using butanol as a reactant. 2. State the common name given to the above reactions. 3. Give the name and formula for the catalyst that is used.from the alcohol (first word) methyl ethyl propyl 2-netty! buy! pentyl hexyl enzyt—epyl_—oety ‘earbon 2carbons Seabons propyt carbons Scarbons Gcartons SS Tearbons 8 carbons = on OO Bak Oo DOG Tt te dca) @ wa 2 BH shea @ GS aba @ Be tore algo © placate, uate g heeds Je 6 ®.@.2 A tab eal 9 gabe - G*eParae ooo o “x K Shanta BW ULeOO Cao ee ee ee a ee Oe OOO a Esters Table of esters and their smelis ‘from the carboxylic acid (secand word)