One week of notes 3/9-3/13
One week of notes 3/9-3/13 CHEM:1080
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This 22 page Class Notes was uploaded by Madison Jilek on Friday March 13, 2015. The Class Notes belongs to CHEM:1080 at University of Iowa taught by Yakov Letuchy in Spring2015. Since its upload, it has received 49 views. For similar materials see General Chemistry II in Chemistry at University of Iowa.
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Date Created: 03/13/15
Lecture 9 Chapter 17 goals 1 Identify the characteristics of carboxylic acids esters and amides 2 Name the carboxylic acids esters and amides 3 Give examples of useful carboxylic acids 4 Give examples of useful esters and amides 5 Draw the products of acid base reactions of carboxylic acids 6 Explain how soap cleans away dirt 7 Discuss the acid base chemistry of aspirin 8 Convert carboxylic acids to esters and amides 9 Draw the products of the hydrolysis of esters and amides 10 Draw the structures of polyesters and polyamides 11 Explain how penicillin works 171 Structure and Bonding Carboxylic acids are organic compounds containing a COOH carboxyl group a Carboxylic acids are abbreviated as RCOOH or RC02H General structure G G p i l l in EDH Jam i EliIf H carboxylic acid Ericxvii mun acetic El ld Esters are carbonyl compounds that contain an OR alkoxy group bonded to the carbonyl C atom Esters are abbreviates as RCOOR or RCOzR Genera l1 atmotur ILL EH35 L HQEHE 513W methyl amalgam Amides are carbonyl compounds that contain a N atom bonded to the carbonyl C F General struotUrJ a ll g a amide H H or alkyl few fe 1 primary 1 amide centains CN 9 nd t is abbrwietel gee Er t iii l tutti CE H H handle and i5 th watd CNH at mm 7 E EH mane i t tertiary i3 emit cantaine titre EN HEEHHEH handle and 5 eateviate RCQHRE R52 ragpreeent tws either identicai it different 33333 radiate itenr39iative t iimmua GENRE feta n t eeee dery 2 amid Lactone a cyclic ester H Thai i m ny am 39is bani En Ft up that ie part at a rim i Cyrizlt eater Ii i t Lactam a cyclic amide fs 5 The earbenyi earbn is bended a NIH i nitr EIi am that is part t a rings we in amide iiEt m 172 Nomenclature Naming Carboxyic Acids To name a carboxylic acid using the IUPAC system 0 Find the longest chain containing the COOH group Apply all other nomenclature STEP 1 Find and name the longest chain containing COOH N EHEEHEHGHEEHECEDH hexane m m u hiexanoit acid is ail STEP 2 Number and name the substituents making sure the COOH group is at C1 EH3 4 l g EHEEHHEHEEHEEEH I W 1 a EH3 1 lwo methy EHEEtiILlE iIE tin iiil and Eli Answer 415Elimr tl flh i i i aid Many simple are referred to by their common names a l D a all N E EHEH in HM W af xes L T L H on EH H I formic acid acetic acid lhE E E at o The carbon adjacent to the COOH is called the alpha carbon The carbon bonded to the alpha carbon is beat carbon fn Earbcin a a y gt F it Hi can 172 Nomenclature Naming Esters HOW TO Name and Ester Using the IUPAC System STEP 1 Name the R group bonded to the O atom as an alkyl group if ethyl group EH5 REHEEHH STEP 2 Name the acyl group RCO by changing the quotic acidquot ending to quotatequot this becomes the second part of the name rimst Ii 1 an a EH53 i EHr Ha answer i ethylcetate derive rpm ateli am if a i h a etai e 172 Nomenclature Naming Amides A 1 amides are named by replacing the either quotic acidquot or quotoic acidquot ending of the parent carboxylic acid with quotamidequot iiiij I H EH NH a I quot denredinwn danwa f eerie acid acetamide beariii earls 45 mmamme HOW TO name an 2 or 3 Amide STEP 1 Name the alkyl groups bonded to the N atom Use the pre x preceding the name r a it I j fiwtm w EH39LNHGHHH 7 i R 5a rmhifmus i t L MWT H NHGHEEiHJS F g 393 i1 1 HG mathquot STEP 2 Name the acyl group with the suf x a m id e quot I E II i i L HIHIEHyEHi in i I I i Eli dni39imti IT39IEIWTI I i itgzr rrire mad if H 4 use immami l e mlquij Em brgi igmtr Haiti 7 e e es ililir IEalquotiiquoti39l39iifil rise39 llilaethylftirmamiie H aiirnethylihenzrnde 13 173 Physical Properties Carboxyic acids esters and amides are all polar compounds Ony carboxylic acids and 1 and 2 amides can undergo intermolecular hydrogen bonding ii iii 0 I in C9 H hi i H CH3 RH e hydidgeniigiond Carboxyic acids have higher boiling points than similar alcohols because there are more hydrogen bonding interactions possible than alcohols 1 and 2 amides have higher boiling points than 3 amides and esters This is because of the intermolecular hydrogen bonding within 1 and 2 0 Strongest intermolecular forces highest boiling point 174 Interesting Carboxylic Acids Simpe carboxylic acids have foul or biting odors Formic acid HCOzH is responsible for the sting of some types of ants Acetic acid CH3C02H is the sourtasting component of vinegar it can be made by air oxidation of ethanol when wine quotgoes badquot Hexanoic acid CH3CH24COOH has the foul odor of dirty socks and locker rooms 174 Interesting Carboxylic Acids Focus on Health amp Medcine Three common pain relievers that are also anti in ammatory agents contain a carboxyl group aspirin ibupmfan Igonon i ll i H E HEDDH ares EH uEHEH ihEEHH t39 31 i I Hm i t jl l a ler I pty39 sh peg JJthliiaZIH l 1P affine H if a EH inf Hi It Ell l 7511an Either H p 174 Interesting Carboxylic Acids Focus on Health amp Medcine Pain relievers work because they block the synthesis of prostaglandins compounds responsible for pain responses in the body H H H H H H H H mail g H l H t H Ellle iii liltile Eli Hm I ii H mathtitanic midi 39ljliill illl39l bl 39 l llin plant 3 lidlift Ell EH Elli H iiill EEIEJH 45 and mmpounds Mimi 11 Eiul LHLH iLHE llama H mg mm m mm hm H E PH ESE g imp Ent gl zfn 175 Interesting Esters and Amides Many low molecular weight esters have pleasant odors Mangos contain ethyl butanoate Apricots contain pentyl butanoate The oil of Wintergreen contains methyl salicylate The amide melatonin is thought to induce sleep because it s production is increased by the body during the evening m l The ester benxocaine is the active ingredient in topical anesthetics The amide acetaminophen is a pain reliever in Tylenol H a ll ll 9 l l M a at azgll ll 3 ill Fenz eaiine eetaminphen 176 The Acidity of Carboxylic Acids Reaction with Bases Carboxylic acids are proton H donors 0 They are weak acids compared to inorganic acids like HCL or H2504 Only a small percentage of a carboxylic acid is ionized in aqueous solution Carboxylic acids react with bases such as NaOH to form watersoluble salts The carboxylic acid donates the proton to the base OH which accepts it D Ell ll ll Na H w H 17 H r 1 Hi w r D Q liri ijlll HEW uz l 5Fif ffl lllji39rl39rl iri t rt 39 This prawn Irm sl rr u Ili iil ll 13hr li l fl 1314 176 The Acidity of Carboxylic Acids Carboxyate Anions Salts of Carboxylic Acids The salts of carboxylic acids formed by acidbase reactions are watersoluble ionic solids i ll GHgi H i Ed H Hat ll massaging a Nat H ail aatania aaial Ibaaa audium aatanaata water nalula water salable To name the metal salts of carboxylate ions put the three pieces below together 3 i 1 name a ftha metal aatlan H 1 parent salsa EHWH l i CHEEHEEEE w Stadium aaatata pataaaium prapanata 176 The Acidity of Carboxylic Acids How Does Soap Clean Away Dirt Etrueture if a snap muleeu e au 1 E E REng HgEH363HEEng HgCIIQCH3EHgEHgElIEEHEEHgEHgEHECHECH gt Li H I E F V I LE E1 EA E L 1 E 1 Egg 1 54 a i i U I i i I i it i t A r a 39939 m a a a a I I n I a a a a a e a e a it a at it I I Ii J T I pit head nnp lar taili init end nnlar end In water soap forms micelles spherical droplets With the ionic heads on the surface and the nonpoar tais packed together in the interior Wife mimeElle 177 Focus on Health amp Medicine Aspirin acetylsalicylic acid is similar in structure to natural products ii39a lll w ETIEEI 3 L quotw L quot 339 7 W E i L A l i n n r H 1 lmyllama smium EEIJiII g39IELTEE39 u EarnHal lrxm I39I39iJIIEI r Wamnl s aim i iilfl ifquot EH3 i j l asgirlri a Hi A Email aa l39r39iisa39liz it l DH is campaigns main mam Irl thin Iiala mam witaw Warm IE Fasaagm 7 I rimuquot gii like mil 1 ill 1m li iml all in iih meaEJ i aspirin ElijiEtEEla a neutral IZHTQEii il mmunti Espirin i iEi ji lll39l li39EiEiI lm it th ir39iEE hi39liEE r 33min man i nii Wl mu z gamma Ernth limit 178 The Conversion of Carboxylic Acids to Esters and Amides A acyl compounds undergo a common reaction type substitution 0 EXAMPLE Here the OR group replaces the OH group G F x H nib i H E a F H Hquot quotE Fr r in 7 39i replacesE 3 pint an H H r picIL a MRI Carboxyic acids react with ammonia to form amides EXAMPLE Here the NH2 group replaces the OH group Heme mile W n ngu 393 Pi is i am marina Ei rT iil iE39 NEH 178 The Conversion of Carboxylic Acids Ester Format0n Formation of an ester is done by the Fisher esteri cation new E band i A H so i all u ll IISEEHE 5 r l H DH HR 7 fa 7 EHEC H on cm H ace l EHq rralplaotaa EH I According to Le Chatelier s principle the reaction is driven to the right by 0 Using excess alcohol 0 Removing the water as it is formed 53 f w m H 5E f a a i CH H mace 7 9quot a H EH b39EWI l39i El lij m h l m39 i ml quot 179 Hydrolysis of Esters and Amides Ester Hydrolysis An ester reacts with water to form a carboxylic acid and an alcohol this is a hydrolysis reaction 0 EXAMPLE Here the OH group replaces the OR group J nw Ill Ell bent i ll in CH i g 4 Hi EH f agj I H ER estir 1 3H repla DH r 0 EXAMPLE Ester hydrolysis using an acid catalyst o The equilibrium is driven to the right by using a large amount of water E El ll HE SEQ H T my E H l H DH qmuE r r If E h quotg H Em H H H 1 a l j a ethyl propaneala Dill rabiesas EEEHFEHE u EXAMPLE Ester hydrolysis using an aqueous base called saponi cation o This basic hydrolysis forms the carboxylate anion rather than the carboxylic acid product 178 The Conversion of Carboxylic Acids Amide Formation Heating a carboxylic acid with ammonia NH3 or an amine R NH2 or R 2NH forms an amide Li D ll M r T a ll Elia l H H H is fuck i a H UH Fl Elli Hquot NH H E lifl ilylllE Elmd H1 or allayl amide The identity of the Ncompound determines the type of amide formed E E lg H IHH 3quot 9 i Ii 2 1 2 V ElIf teem EH We acetic aeid emmeme r amide 3933 G F g H H CH 3 g I Hamlhylaeetamide g Al1ji ra i 7 magquot tee g mg HHHEHE H 39 El EFIE and mehyllamme E amide ii is MHVrdimethylatetamlde I a HSH EH a 7 Eli EH EH EH5 EHiEHigE CH3 aeehe eld rdlmet ylamme amide 179 Hydrolysis of Esters and Amides Amide Hydrolysis Treatment of an amide with water in the presence of an acid catalyst HCI forms a carboxyic acid and an amine salt Mamethylpmpanamide V is H HIEI r E taw r i HE39D39H I ZZHEGHP MHEHQ armada 1 m th4I th 1741 H Pmpami a id e 1lquotamr39I sirr39Iillrn It on e U 43 v l Ht EH H E H fb ltyll eld amine gall Amides are also hydrolyzed in aqueous base to form carboxylate anions and amines 7 henearnitle H 77 M e H l l H m iy amen ammma 179 Hydrolysis of Esters and Amides Focus on Health amp Medcine Triacygyceros common naturally occurring esters contain thee ester groups each with a long C chain 0 They are lipids waterinsoluble organic compounds present in fats and oils G l SHE El i H El Fl groups haw lll IE Ts l Eli 3 H lem at r ELIowe dammed in redI i L EenEral ljrunrnula of esters R JillEli39lH ElHEEIEJ r EmFl39 where H an alkali aryl or erwaiwes anti H Hallwl awl or dammitres triagyiglly rl Illiyl FITEIIEQI I EDE saturated or U EaTLHTEIEEEEl Tlriacylgilyeemls are called in medical and f d literature Animas store energy in the form of triacylglycerols Using enzymes called lipase the 3 ester bonds are hydrolyzed when the triacylglycerol is metabolized o Diets high in fat lead to obesity so the quotfake fatquot olestra Olean was invented to replace some triacylglycerols in snack foods The lipase enzymes cannot hydrolyze the olestra so it passes through the body unmetabolized providing no calories to the consumer Fl 8ng i I L IN VIIla H Tray William Iiiman ea 3 r u i 5 El I39li lilyl1 Fi a H 739 wr w r r quot F 1 quot 1 39 I HE F El Hi I39 H39 li hgnip ll Vlfhikig EH 5 5 393 I39l 3923 lit 1 393 i i u c i E I I F ijlu39uii Tli anw39ailn ling Ni 5 l g r l I I gt gt 3 CD39 i gt FL gt3 ifquot H g I 391 I L 372 L in mp liinviriaia il gal Winn li lawn in sulfa m Eatmp f an LII39IEHELIFtE39dl mt trii I Grid Elhiaminal fnnrnlila39 H H E FE hi 3 39 ax palmitit acid a quotit niemaoicl m I quot if alphalinolani acid Glycerol glittering m 1710 Synthetic Polymers Nyon A Poyamio e Nylon is a condensation polymer formed when two monomers come together releasing water IHHHI39IE H IT39HEI39HT I Emljl39r Hill Willi illji l n r i H H i HEN mini may llf iquot with r iiiii a rim Henri my u Hi i filing r em iliv39nil iLLui E inl ia Hiq lngniii I if H Iii H ii iii ii I Ill H i H ijiigligih u c if my r H 4 iii 4a 2 riillgfriinli 4 rm iihl llljiii lumrin i u plliil M l HgrainRialHg n appealac mH m E ai a a iHFR39HiH39 i En H33 H93 representatives ir11rlanEl nylon nylonam nylana aii nylanaiii WIDHJE and WW4 1710 Synthetic Polymers Poyesters The most common polyester is polyethylene terephthalate PET used for materials Dacron and Mylar and in making plastic soda bottles 0 PET is easily and cheaply made and forms strong stable materials i Ci p p 775839 Edi in SHEERHg Kn EHJEHE E polyethylene Eereph mlai a 1710 Synthetic Polymers Focus on Health amp Medicine So Wy degrading polyesters are useful in making sutures The mending tissue is held together for a length of time t heal and then the sutures break down C u it a EH DISH EH quot 3H 1 f new 3 D l lil Ea dissolving suture material n H EHHE QH It n HE HlEH l Ea I39l aEH HiEH lE irr GIFEGHG avoid Lamina avoid 2n HE H39ytlr quih anuiu ElHydrawpmpanui j FilLE hincumpaiible polymer 1711 Focus on Health amp Medicine Penicillin Penicillin is a group of antibiotics derived from Penicillium fungi 0 The antiobiotic properties of penicillin were rst discovered in 1928 by Sir Alexander Fleming 0 Penicillin antibiotics interfere With the enzyme that synthesizes bacterial cell walls killing the bacterium ll enoilins mntain HE E Ia tam n camEarn H El fm Laotama yollir amidea H dii EFEF39II gzrnupsa for diffsram i illl 1711 Focus on Health amp Medicine Common Pencilins Used Today IH39I IIIWIIIT39UIII l HITII HIIIIUH
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