Midterm+1+Practice+2009 (1)

Midterm+1+Practice+2009 (1) - Chemistry 112A Midterm 1...

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1 Chemistry 112A, Midterm 1 Thursday, October 9, 2008 Student name: Student signature: Write TA’s full name (section number) or Lecture Only: 1. Please make sure that the exam has eight pages including this one. 2. Please write your answers in the spaces provided. 3. Write clearly; illegible or ambiguous answers will be considered incorrect. 4. Only writing implements are allowed (No Calculators) . GOOD LUCK! 1. 12 points ____________ 2. 50 points ____________ 3. 40 points ____________ 4. 13 points ____________ 5. 10 points ____________ 6. 10 points ____________ 7. 20 points ____________ 8. 20 points ____________ Total 175 points ____________ MINI-PERIODIC TABLE I H Li Na K II Be Mg Ca III B Al Ga IV C Si Ge V N P As VI O S Se VII F Cl Br VIII He Ne Ar Kr
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2 1. Provide structures for the following chemical names (12 points) 1-isobutyl-1-neopentylcyclobutane 4-ethyl-3,5-dimethylheptane ( E )-5-isopropyl-6-methyl-4-nonene (2Z,4 E )-5-ethyl-2,4-octadiene 2. Answer the following questions. Points will be taken off for incorrect answers (50 points). (a). Circle the alkenes that are (Z) stereoisomers (6 points). Br H D Cl H D H H 2 B (b). Circle each alkene carbon that is a stereocenter (6 points). (c). Circle the energy difference in kcal/mole between the gauche and anti forms of butane (5 points): 0 . 9 1.4 3.0 4.5 5.4 (d). Circle the correct statement(s) (5 points). 1. 1s, 2s, and 3s orbitals do not have any nodes 2. Conformational isomers have the same molecular formula. 3. π -bonds are cylindrically symmetric. 4. In concerted reactions all bonds are broken and formed at the same time. 5. The smaller the standard free energy of activation ( Δ ), the faster a reaction proceeds.
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3 (e). Number the radicals according to stability ( 1 = most stable ) (5 points). C H H H C H 3 C H H C H 3 C H CH 3 C H 3 C CH 3 CH 3 (f). Circle the compounds for which each atom has a filled valence shell (5 points): BH 4 CH 4 3 NH 3 NH 4 (g). Number the bonds shown from longest to shortest [1 = longest ] (5 points). HO H H 2 CO H 3 CS e H H 3 CH H 3 COH (h). Circle the Newman projection(s) that represent a lowest energy conformation for each compound being illustrated (8 points). H (H 3 C) 3 C CH 3 CH 3 H H H (H 3 C) 3 C CH 3 H H CH 3 H H 3 C CH 3 H H 3 C CH 3 H H H CH 3 H CH 3 (i). Number the alkenes from most to least stable ( 1 = most ) (5 points).
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4 3. For each of the following reactions supply the missing starting materials, reagents, or major organic products in the space provided. If no reaction is expected indicate by N.R. (40 points total). (a) HBr, O O (b) 1. BH 3 2. NaOH, H 2 O 2 (c) 1. O 3 2. Me 2 S (d) Br 2 , CH 3 OH (e) OH (f) D 2 , Pt (cat)
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5 (g) DCl D Cl (h) HCl 4a. Draw an energy diagram for the different conformations of the alkane shown below. The energy diagram should reflect the relative energy differences between the conformations, but exact energy differences do not need to be shown (8 points). 0
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This note was uploaded on 07/05/2010 for the course CHEME 140 taught by Professor Radke during the Fall '09 term at Berkeley.

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Midterm+1+Practice+2009 (1) - Chemistry 112A Midterm 1...

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