Chem 3331 Samakia Spring 2010 Midterm 1 9:00 SECTION 10 Student ID page points: 2 (24) 3 (20) 4 (20) 5 (24) 6 (12) Total (10) Periodic Table Ha H Li Na K Rb Cs Fr Be Mg Ca Sr Ba Ra Sc Y La Ti Zr V Nb Ta Cr Mo W Mn Tc Re Fe Ru Os Co Rh Ir Ni Pd Pt Cu Ag Au Zn Cd Hg B Al Ga In Tl C Si Ge Sn Pb N P As Sb Bi O S Se Te Po F Cl Br I At He Ne Ar Kr Xe Rn Ac Please sit with an empty seat betwen you and your neighbors. Unles specifically asked, you do not have to draw mechanisms for reactions. Fel fre to ask questions about the questions, but please don?t ask questions about your answers, it distracts your neighbors. Chem 3331 Samakia Spring 2010 Midterm 1 Student ID #_____________ Page 2 of 6 1 Provide the products of the following reactions. If a reaction would produce stereoisomers, draw the isomers and indicate if they wil be produced in equal or unequal amounts (4 pts each). a) O ! b) Br 2 (1 equiv) c) Br 2 /FeBr 3 d) H 3 CH 1) BuLi 2) CH 32 Br e) H 3 CCH 3 Na /NH 3 f) H 3 CCH 3 H 2 /Lindlar's catlyst Chem 3331 Samakia Spring 2010 Midterm 1 Student ID #_____________ Page 3 of 6 2a) Provide the major and minor products expected from the reaction shown below and indicate which is major and which is minor (6 points): b) Is this reaction under kinetic or thermodynamic control (2 points)? H-Br (1 equiv) 3) Complete the following syntheses using any organic molecule of 4 carbons or les and any reagents you need. You do not have to show the synthesis of the 4-carbon or les molecule you use. If your synthesis requires more than one step, provide the product after each step. Al chiral products are racemic mixtures. a) H H O (4 pts) b) H Me OH (4 pts) c) (4 pts) Chem 3331 Samakia Spring 2010 Midterm 1 Student ID #_____________ Page 4 of 6 d) HH O (8 pts) e) H O (12 pts) Chem 3331 Samakia Spring 2010 Midterm 1 Student ID #_____________ Page 5 of 6 3) Provide the products and mechanisms for the folowing reactions. Show every intermediate with the proper charges and al the arows required for each step of the reaction (4 pts for product, 8 pts for mechanism) Cl O AlCl 3 3a) What is the approximate pKa of acetylene? (2 pts) b) For the conjugate base of acetylene (shown below), what is the hybridization of the orbital containing the lone pair (circle one)? (2 pts) H (-) Hybridization? S P SP SP 2 SP 3 4a) Provide the hybridization of the atoms indicate with an arow below (not the lone pair orbitals, but the atoms). (2 pts each) N O N H Hybridization? Hybridization? b) Are the following molecules aromatic, anti aromatic, or does this designation not apply? (2 pts each) N O N O Chem 3331 Samakia Spring 2010 Midterm 1 Student ID #_____________ Page 6 of 6 5) Label the boxed groups as homotopic, enantiotopic, diastereotopic or does not apply. (2 pts each) OO Me H OO Me OO H OO Mee Me e 6) Butadiene has four ?-orbitals caled ?1 ?2 ?3 and ?4. ?1 is lowest in energy and ?4 highest. The p orbital systems for ?2 and ?3 are shown below but without the phase designations (?1 and ?4 are not shown). Provide the phase (+ or -) for each lobe (2 pts each) E !1 !2 !3 !4 Tarek 2010_3331_EXAM1
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