Biochemistry Name: Unit 2 “Organic Reactions” Period: Date: (‘cids-Base Reactions — Practice Questions Refer to the attached chart when needed. ~~~Questions & Problem: 1. Ammonia appears in the table as both an acid and as a conjugate base. (a) Explain how ammonia can act as both an acid & a base. (b) Show how water can serve as both an acid and a base. (c) Show how methanol (CHsOH) can serve as both an acid and a base. Write an equation for the reaction of methanol with sulfuric acid. 2. Write equations for the following acid-base reactions. Use the information in the Table to predict whether equilibrium will favor the reactants or the products. fa) HCOOH + "CN (b} CH3COO” + CH30H C (c) CHsOH + NaNH2 (d) NaOCHs + HCN {e) HCL+ H20 3, Each of the following compounds can act as an acid. Show the reaction of each compound with a general base (A-), and show the structure of the conjugate base that results. (a) CHsCH20H (b) CNH (c) CHsCOOH 4, Each of the compounds above can also react as a base. Show the reaction of each compound with general acid (HA), and show the structure of the conjugate acid that results. 5, Show the product of protonation on the other (-OH) oxygen of acetic acid. Explain why protonation of the double-bonded oxygen is favored. 6. Rank ethanol, methylamine, and acetic acid in decreasing order of acidity. Explain your ranking.7. Rank ethanol, methylamine (pks 3.36) and ethoxide ton (CHsCH,0°) in decreasing order of basicity. @) ©) © @ © © Explain your ranking. Write equations for the following acid-base reactions, Label the conjugate acids and bases, and show any resonance stabilization. Predict whether equilibrium favors the reactants or products. (2) CHCH:0H + CHSNH (e) CHNHs* + CH3O" (b) CHsCH:COOH + CHsNHCHs (f) CHsO" + CHaCOOH (c) CHsOH + H2SO4 (g) CHaSOs' + CHsCOOH (d) NaOH + HS In the following acid base reactions... 1. Determine which species are acting as acids and which are acting as bases. 2. Use arrows to show the movement of the electron pairs in these reactions, as well as the imaginary movement in the resonance hybrids of the products. 3. Indicate which reactions are Bronsted-Lowry acid-base reactions. ca-t—u + po seeuldhyde gee Ce i cnt ca cE] + : o ' CH—C—-H + CHO > CCH acetaldehyde o-cH, “BE, BH, + CH,—O—CH, —> CH,—O—CHg 1 CHEK + “OH > CHF“ 9 1 CH,—C—H + “0H — CHAN, + CHC > CNH, CH, + Cr|. © :NH, one donate A prtn yyy O Can accept « protm Nyt © hao: Hyo + NH, = = OH” + NHyt BASE? HOt Hel = Hjot+ci~ @ puv: cH0H +NH; 2 po BASE: cH 0H + H)50, 2 Chong P+ Hs04- E ] A HE ee WEAR Bag; ws Hog? 4 HEN 7 | pka= 376 —? Ot aC ka = 4,22 iD — P “ Weaker Ctcoo” + ab0H => Ctt,CooH + CH,0~ , ka ¢— Reconance (weal) i S pee “ZY a ei Nut @NH © cttyott 4hNaNt, <= ct,0O+ NH, tl pka 6.5 — oo pka 33 (A) Coct, + Hen = Hol, + Nan : pee pkala> Nat N Of fo. ee 4 (I~ (hong hid) ——>@® thot + cto" = tho +chHsoH i keg 2 3.2K 10% @req —3 3 x10 (Prducts) ® ® CH,cHoH + AX oN : cup) RP OynNR > weak, Acid base Strong base Wl cH pO? CHy-G-OH @rio G > CHyNH, + AT fl oi A - a -N CHy-NO + AD = CHa-NeS H H CHy-NS or CHa“ NSH (®RIO © cHycoo + AP ‘| c 0 0 ye NE & cute Cis-c-OH tA = Hy-€ > + HA CH -EO® Aerio4 @© Cusct,-OF8 + Hee (qe) Proton bonds + an epair! CH,CH-C2H + ©. _ 7 —_CHa-NAQ ot HR = cw, +AT © [Os sae oe 8a cn-e-6u HATS YEH C a @0-H - > ay e-5-# > Cage 4+HA d o-H# = an cH3- 20: a o,- 6 aie We op tp H : (No RESONANCE!) i CHy- b-O-H + HY 2 resonance Srectures! Show Above !@) CH OH + H2S0y * 0 CH —o- H + Me -O-HS So_ 5-H 8 ee on 7 ° # (wa) Hay | °° 4 ©0=5-0- & 0=5-0-H & = g-o-H 0 oe oe @ ‘O-H + vem = ‘OH Sy 7 a S layer O Hl H '® O_~ ’ i CHy—NsH + CH,-O" =F CH3—N: +11,6-8 H aa cA s6 C—») WA we© acetic Acid > ethanol > Methylamine pkas4tt pkaz 15S pka=33 % Eoxide lew > methlyamine S |thanol pk p= 2.36 etnanol CHsCtLOH “= CH CHO Aci etoxide lb Cons BASE! pkar 5S (Arona base) ee a ieee enemies . @ yea —oH + CHs-NOHS CH CHO? + CH3- NH. OF more stable (weaker base) © teneq N ee CHytl, -C-O-# 2 5A. : & a) dip C-O Ce Otte -c= W. A, 4 CH, ca a Resonance6 of ul | CH,-C-H +S0H — CHs-G~-H# gD nee (tH, — ¢ -H 45. ‘0-H 20: I cag AUD BASE :O-H © 7 HQ: He CH, _t-4 +70H |g! t-H? yteC-H eo i of eo: H gO: H ioe HO bg C-H 4SO-H = |p-gec-Hes y da eu| i Brgnsted-Lowry Acid /Basey + Hee Ha-Nih + CHa-CI3 CHg-Riy-cH, C17 yo-N-H + HAGE Cl ss H,C-N- 4 +¢\~ y 0 a 3 HH 7 h BE fad*. © bromled-Lovey (Pebn Hess). ie Ble O has Sve oN Cz — Ly + HE} coe CO-H _ Ctts—C—H men 7 neal BASE Aad _ a MINOR, © 05 ‘OF | 7 { CHy-coH +t CHP CH C-H :O-CH electrophi @ nucleophile, * 3 © BH; d Ae , BH g — Ch ~ Lewis Acid- Lewis Base 3 (ear Aetpts) Ce pair Dna)(NO resonance.) 7 Cc» Ch OF FOO St o-H au Os i I er | 0H,-63 og tHs-é=0| , (resonance) 3 resonance oe |te-Er0 Q resonance More Staee © = weater!