Organic Chemistry Exam III for Chem 2321 at Seton Hall University - Prof. John R. Sowa, Exams of Organic Chemistry

Download Organic Chemistry Exam III for Chem 2321 at Seton Hall University - Prof. John R. Sowa and more Exams Organic Chemistry in PDF only on Docsity! Name_______________________________ Chem 2321 Organic Chemistry Lecture Seton Hall University Instructor: Prof. John R. Sowa, Jr. June 20, 2007 Exam III 100 points Q1________ Q2________ Q3________ Q4________ Q5________ Total_______ Good Luck! 1 AYOLVHOSV] TVNOLLYN SOWIE] SO] « TF ae) GB. | (| | SS, | [EE | [ER] [S| | SE] [Se jomeees |] Seeba | ecimrar) | een |] omeitiy || mille || toe || tee || pean FT} ON || PIN | Wr] Sa |] JD | I fw] uy ~ssuesepuey ‘OL cOL LOL OOL 66 86 L6 96. S6 Set | || Sah | | SA | [eta | [ee] [SL | | akttte || RSS. PSpdrysalend | | gy epee quhgs?P xd eulhy'3t vega sl ergata Pagethd aca nT GA || WL) Ja || OH sa QL py ny 4S9U19g OpreeypU'] LZ OL 69 89 L9 99 so 9 £9 @ (sez) (62) Ua ey [en ee, OD, wa | az, | [ Wee) [eee arses | [peste] [peta] | ea] nee ae || Se on yng, bug Ws) ua | 3s qq ey) ay 8L QLL PLL 60L 80L LOL 901 SOL 88 £3 2 ||) | a) (| zee | | cua | (com |) Sot) soe fg |[ =e beaaracreshdl hacrivesed (yom nad Hearse) PayPal eronestad| |espement’ | | risers] grunt | oS menbd | lepygny had wim || jab WA || WV | Od || a |) Id Wd |) AL |) SO}; PH ]) MW |) BL vg || SO 98 S8 +2 £8 zB SL £t ot Sé tL eL 9S SS te [|| 2 |( sor 2 || SE) [ee | (ee | || SS Hae, || eke syria | | gtsqprmiat| | Sarre) | lsypreedod| | chy ental mac || gpredon | | yea pasta | | preuan” | | gems wid || Sar 3X I |) AL |} 4S |) us Pd |) 4a |) |) OL |) CW |) IN IS || Wa vs es gs LS OS oF Sv tr tr au Ly Be Ze oes 06"6L OGRE wobL BSL f6RS sess 6" oes FOOS { wor) Ores. ims | inn) tion [osm | fbi || 2 || pete | | eae || Haw || toe or ||" WJ || 3 |) 2S || sy |) 2D IN |} °D |} 9 || GIAT]) JO]; A vw) 9f Se be €e ze 87 £@ 9% Sc be EZ 0% él we || ate || Woe | [fsa || ee ag al ao as ent! BE stead || esc | | descend | | gacscien! | | pdcpscton ‘Selon! lead TY) ID] $ || d |/ is SIN | &N SL du OL SL vL tL LL Or 00°6T om oer TOT 710) TH69 oteema || sey || yeeaen | | Seceor || ance Meet || soon ®N|| J | @ || N|| oO eq) FI OL 6 8 z 9 v £ % Vi Wo Ws Vr VE Vv SOOT a S]UBLW9|J 94} JO BIGe] I1poLaq © [a aH H cz L uorsrarqg Ansmuayy Aroisoqe’] [euonenN sowrypy soy VI 3) (20 pts) Mechanism of SN1 and E1 Reactions For the following reaction: a) (3 pts) Which product is the SN1 product?_________________ Which product is the E1 product?______________ b) (14 pts) Write a mechanism that explains the products of this reaction. Note that the products are formed via a common intermediate. c) (3 pts) Another E1 product is formed in this reaction. Draw the structure of this additional product (mechanism is not needed). Explain why this would form as a minor product. 5 OH HCl (aq) Cl + 4) (18 pts) Mechanism of electrophilic addition reactions. For the following reaction: a) (2 pts) Does this reaction occur via a Markovnikov or an anti-Markovnikov pathway? ____________ b) (12 pts) Write the mechanism for this reaction. c) (4 pts) What is the product of the following reaction: 6 HBr (g) peroxide inhibitor Br HBr (g) O O O O (1 % added) 5) (24 points, 3 each) For the following reactions, circle the major product and indicate the type of reaction, i.e., SN1, SN2, E1, E2, etc…(not all choices given). Rxn type i) ii) iii) iv) v) vi) 7 O K Cl vs. H Br H3C Ph Ph H CH3O - Na+ CH3OH H3C Ph Ph vs. H3C Ph Ph CH3OH Cl vs. CH3O - Na+ Cl CH3OH OCH3 + OCH3 HBr (g) + peroxide inhibitor Br Br HBr (g) + peroxides added Br Br