Organic Chemistry 1 - Exam 1 Questions | CHEM 2321, Exams of Organic Chemistry

Download Organic Chemistry 1 - Exam 1 Questions | CHEM 2321 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 7, 2007 Exam I 100 points Q1________ Q2________ Q3________ Q4________ Q5________ Total_______ Good Luck! AYOLVHOSV] TVNOLLYN SOWIE] SO] « TF ern | | EB | | om een] | SE | | on lSEs | | lh oi oe | | afl E Lermomeeh || esta | Maa] | ed, |] gear || Meu? | | settee | | pute | | Spon FT |} ON |) PIAL] Ger || sat |] JO |) Ig || wo|| wy ~sones apmmey €0L ZOL LOL OOL 66 86 L6 96. S6 SS se Sab | | aint CRS | | wtents | | ancine (Pp deysalend real quhgs?P xd eulhy'3t vega sl ergata iPseethd aca nT GA || WL) | a OH sa QL py ny 4S Oprereypuey 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 aa || om on yng, bug Ws) ua | 3s qq ey) ay 8b OLL PLL 60L 80L LOL 901 SOL 88 £3 |), ae || || See me Zot | eu || cet || om | | ae a || ss Learned] Lary eee] yes mated Hharsoneteal Payphyne sel epsrimznen | |espumened | | rvumeston | |gry yates | |e | |esygty Pal in (be wy || tv || Od || Ta |) dd IW | 3E |] sO }] om |) AM] BL eg || so 98 S8 #8 £8 zB BL Lh OL SL ve €L 9S SS ter |[ oe |/ sat | (ee ifm ERM || Sa | [kim | [ies | (ten ] | EE TEs, || ke syria | | gtsqprmiat| | Sarre) | lsypreedod| | chy ental mac || gpredon | | yea pasta | | preuan” | | gems wid || Sar ax |] 1 | aL | as] us Pd | 4a OM |) OL | OW) IN Js || a vs es ts LS OS ld Sv tr tr au Ly Bt Ze oes 06"6L O6'8L wobL BSL f6RS sess Fo" oes FOOS { wor) ores. ims | inn) tion [osm | fbi || 2 || pete | | eae || Haw || toe or ||" FJ) 3@ |) 9S || sy || 99 IN | 09) ag |] UAL) 39 |) A ey || ¥ 9f ge be €e ze 87 £@ 9% Sc bz EZ 0@ él we || ate || Woe | [fsa || ee a8 al a9 as vent Oe otceed Arete | | sdgsciond | | deacion! rdigaiond ‘Selon! hw SV |) ID) S || d || 5s SIN | UN SL du OL SL vL ZL LL Oe 00°6T om oer TOT Z10' TH69 oteema || sey || yeeaen | | Seceor || ance Meet || soon ®N |] J |) @ || NI} o ag |) FT OL 6 38 £ 9 v £ iF VL v9 Ws Vr VE Vi BOOT my SJUBWA|J 9} JO BjGeL IIPOLWeg c/a aH H Zz L uorsrarqg Ansmuayy Aroisoqe’] [euonenN sowrypy soy VI 3) (20 pts) Structures. a) (12 pts, 3 each) Draw electron pushing arrows showing how the resonance structure on the left are converted to the resonance structure on the right. Add formal changes to the structure on the right. b) (8 pts) Convert the following “stick-figure” (line-angle) drawings to full structures showing all atoms, lone pairs and bonds. i) ii) O O OO O H OO N NH2 4) (20 pts) electrophile/nucleophile chemistry, -bonding a) (10 pts, 5 ea) Identify the nucleophile and the electrophile in the following reaction. Draw an electron pushing arrow showing how the nucleophile attacks the electrophile. i) ii) b) (5 pts) In the following structure, draw in the unhybridized p orbitals and show how these form -bonds on each C=C. c) (2 pts) Are the CH2 groups on each end of the double bond oriented parallel or perpendicular to each other?______________________ d) (3 pts) In the above molecule indicate the hybridization for each carbon present in the molecule. I + I +H3C Br NH3 H3C NH2 + HBr CH2H2C 5) (20 pts) Functional groups and molecular properties. a) (8 pts, 2 ea) The following compound is an important steroid in the human body. List four functional groups present in the following compound and indicate where they are in the molecule. b) (6 pts, 3 each) In each pair of compounds, circle the compound with the highest boiling point and state the dominating intermolecular force of attraction that occurs with the compound with the highest boiling point. i) dominating force of attraction ii) c) (6 pts, 2 ea) In each pair of compounds circle the compound with the highest polarity. i) ii) iii) O OH vs. OH O vs. vs. vs. H O H H3C O H vs. Cl ClH H Cl ClH Cl