7 ; PI Aridersor ft OL co CHE 3322 S Exam Il lo? November 21, 2011 ‘Work four out of five problems. For extra credit you may work all five, but clearly indicate the extra credit problem. : 2 Si. ‘Complete the following and indicate. nm Oo CH;ONa/CH30H Clason - conctunpakion 1) NaCN/acetone cé « "Oo K B.2bromobutane ay CH CH MaBeIEt,0 & cede 3) H,0" On? H*, heat c, HO® y a NaOH D, 3-pentanone + benzaldehyde Pee + Ve ecdee 9 Ghee 1 Natt 2) L-bromopropane 0 3)HO+heat = _ veow EB NH a F. acetic anhydride + cthanol a ( BVEew, + EtOH rec C-0ce _# IL. Give a Teasonable Synthesis of the following ifom alcohols of four carbons or less and/or benzene, diethyl malonate, ethylacetoacetate. A. 3-bromofluorobenzene B. er eee C. pheay! isopropyl amine coff ee " ey “ ween . eo wl oo el? e 5 yp rea cher © ott mae pe bo te tin yt Give the cone mechanism forthe following. Clearly show electron flow. ———» product + water A \ a 7% ate xe Z ou = * me O46 COG Oho SS han ANIMA 1S HL Sivenger & GaiAGII ates bees el AP sag on poniyousiins Consiga) « sewiOnte Suche’ duat pers 0: posite Remal erage on ALL yale grog) pula HS Tok plecerens in Ord moving ML Loe pais less cwaileche © accept A Qroton. Anilv's electons ax note reallly bl cept & poten kof ane plactroegae (less B. Which is more reactive towards hydrolysis, amides or esters? Explain. ( EsteS. Aynides cave Less reactive towards the nucleopl & alse a Usaher ew Spr lie ond b LO molecule fen due to vi Needle ute. amie cenusalig She artery! ee SO on the Caren CarbonC. Why does aniline not react via a Friedel Crafts allylation? What can be done to transform aniline ato -isopropylanitine? | a, “ats i eens “C1, Alig os Sy NT © —> 7 ° a ‘ etc ACLs y Le, yy O Cor 46D. Which are more acidic ketbnes or ester Jetones, TH oxyg.Ln ok Hae etter to WAP Stebitter He SD OQ Hr lessen Hu £lUcHon pelanratien ere OE Also Mole XH to Veact On a Iretone an ester, 4 E, Free radical chlorination of propanal with chiorine gas will from propanoyl chloride. However, a major contaminate is 2-chloropropanal, Suggest a mechanism for the formation of this contaminate that ig nota radical mechanism. ~ . o 2 8 el COURS Cy Se ECCT Cee 2% é He gow " : ceccit =F coc. te CCC- CH; 2 "S i a G S V. A How are reactions between aldehydes and nucleophiles fundamentally different than 2m reactions between acy! chlorides and nucleophiles? ¢ ) Acyl chlorides have a leaving group, CI, whereas aldehydes do not. 4) Aeyt chlorides ly form enol tautomers. B. Which one of the following does not react with benzoyl chloride, CsHsCOCI? i 2) 0H 3) (CNH 4Y(CHssN ¢ — C. Which one of the following is not a good way to make ethyl acetate? 7 Sa Catalyst