Grade 12 University Prep. Chemistry Unit 2~ Organic Chemistry scHaU Organic Nomenclature Package C: Ethers, Esters, Amines, and Amides ‘This certian continues the discussion of four other functional groups by examining two oxygen- containing functional groups within hydrocarbon chains such as the ether group (RO) and the ester ‘group (* Hoes ). We will also be examining two nitrogen-containing functional groups known as why amines (na) and amides(” ) Table 2: Structures and Examples of Ethers, Esters, Amines, and Amides Generar Sacre Tye Example with UPAC Name wh WH Rok emer | e-deo-e-ben | ethowethane AA HH ester hy Pt ‘ethyl ethanoate Hoere-o- eH HHOOOW a amine ar aminomethane ‘ i how { ae wb amide webb ethanamide 4 Hw Naming of organic compounds Involving these functional groups follows similar methods usedin Previous types of naming but they do have ther differences, as explained "Naming Priority for Functional Groups: Eee ao ocean tie ‘sie co Alyse a Fem -c#=0) ‘owe = ‘ke en ne ‘gan ‘sae ‘ae ai ‘Al ae ae theGrade 12 University Prep. Chemistry Unit 2 OrganicChemistry ScHAU A. Ethers. ‘+ Oranc compounds that have an oxygen attaches to TWO hydrocarbon alkyl sins 2 Geneatformis BOR + Toname ethers © Pai Islkony group (= shorter hydrocarbon chain) "othe carbon atom [om parent chain) Bonded to onygen~ ‘other de groups onthe parent en (eat location # with same, root name of allzuy group” + "oxy" .© Hot akane name ofthe longer [parent chain Bonded to oxygen starting at the end cosst to onvgen) cy uC, cH, s—JL___4 puentakane idegroup akon group herane methyl Spropony ‘oroopar4 methyhexne Examples: wae = wttotta Wye ethonhesane enonyetane oR cH Hye ae I CH3-CH—CH)-CH3 2methoxybutane CH: = Ow Oo Methonybenzene 2-methoxyheptane ‘methonycyclopentane 2-methony-S-ethylheptane 2-methoxy-5-chlorohexaneGrade 12 University Prep. Chemistry scrau Unit 2~ Organic Chemistry LOCH -0- CHOCO EAE, Chet gr OOO, a Hye-eHFCHEGH- CHC, oo Ji._Draw the structure ofthe foling: 3 2butony 3-methylheptane b. 2-propoxyhexane © Spropoxyectane: ‘d._-methoxymethane ‘@. Rnethony-3.3-dichlorobutene F Sethonjectane-t, 4diol ‘Additional Textbook Practice for Naming Ethers: p. 69 #136-146, 31Page‘Grade 12 University Prep. Chemistry ‘Unit 2— Organic Chemistry scHau B. Esters tates co esponsibl for many of he atl sad ate in products chery coke for example o_o — [OT TTT eo cet 1p Goer form ote ata acne ta angen aces aaa caor vin coaioneedia nin Sere acheto od coton chan 3 cabo hance opt Pevre'bipeya® nowy scpnemenae fain =p neta terrae stereo eid Fo "Riesbaneccon wancioe ve gps ontaoaeione oa caka 8 4 S-C-H = ramps: ey tutnoate seth provaneate Aw Hye ~O" propylethancate [etted seer becancote propyl 2chloro:3-hydronybutenoate 4[PageGrade 12 University Prep. Chemistry ScHaU Part B- Practice: LL Namethe folowing: Mann Unit 2~ Organic Chemistry [e | CH.COOCH.CH.CHICH.CH.CH.CH.CH, ° crg0-L-crrcnros, : Br ASL ——, pho cl he ‘CHCHCH.CH.COOCHICH:). Draw the sractares of the Tolowlne “Mati methanoate 1 Benaylheptanonte ‘© d-chloropentyl -mathjloctanoate Teaprepy banat 4. propyl benzoate \sobutyl 3-luoropropanoate [Additional Textbook Practice for Naming Esters: p. 65 #126-135 SlPazeGrade 12 University Prep. Chemistry scHaU c. Unit 2 Organic Chemistry ‘Amines are an organic compound which contain a nitrogen attached to one or more alkyl groups ‘Amines are classified as primary, secondary or tertiary depending on the number of alkyl groups (R {groups bonded tothe nitrogen. o a Peary "1 Examples Primary Amines (Use the format ‘akann-amine”, where nindizates the postion ‘ofthe -Ni group) | Secondary Amines — | (de the sui "ly to identity the secondary chain attached tothe smethanamine oct NH, proper-2amine Semethythexand-amine ee "Noy oH, cone Nemethylethanamine | _Neethyhexan-2-amine _N-Methylpropan-2-amine re (nan tn < | exonon ont) chain attached to the amine group) methylpropan-2-amine Nethypropyibutanl- | amine methylcyclohexanamine Part c- Practice i) Identify each ofthe following as primary, secondary etary amines AND give the covet IUPAC name: 3 ic re | nemenonp a” ¢ a eoGrade 12 University Prep. Chemistry scHau Unit 2— Organic Chemistry e e ATL & i 1.__Draw the structures of each ofthe folowing: @ TAHluore-3-hydroxynoran-d-amine ‘. Semethylhexen--amine © Neprop/hN-peniyliexan-2-emine 4. N:sopropyibutan-I-amine @. Nnedimethyi2-chloroheptan-S-amine: ¥_ N-butyN-ethyl-2-methylpentanS-amine TeazeGrade 12 University Prep. Chemistry Unit 2~ Organic Chemistry scHau D. Amides ‘The amide hasa structure similar to the ester however the oxygen atom in the chain ofthe ester Is replaced by a nitrogen atom, thus giving you the amide. It occurs from a reaction betwaen an acid and an amine, Naming amides is similar to naming esters. The first part ofthe name comes from the amine. ‘The second part of the name is derived from the aid. The ~oic acid ending is changed to ~amide. ° ° ° es a ra i Bima Seema) Tons 81 Examples Primary Amides H, (Use the format | “akane”+ amide) Hy ts (oO ‘2methyloutenamide Benzami¢e ‘Secondary Amides (Add the sual” to identify the secondary chain atached to the amige group) emovanoie ary Amides 3 cee I? (add a second suffi one ‘stolen tbe wos stor chin attached tothe amie | "*2nenvormeamee | \.ety.Nmethyethanamide | Neey-N-methybenzamide up) Part D- Practice: Identify each ofthe following as primary, secondary, or tertiary amides AND give the correct IUPAC name for each ofthe following:Grade 12 University Prep. Chemistry Unit 2 Organic Chemistry ° early {= heptanamide b. N-butyihexanamide Nepropylethanamide 4. Neethy-N-methyipentanamide |". Neisopropylethanamide T_2.3dichloro-6-hydronvoctanamide & 2methylpropanamide fh. Neethyl-V-methy/-3,4-dichlorononanamide Tg mis9.168