Sample Exam 1 Key - CHM 1240 Exam 1 Please print your name...

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Unformatted text preview: CHM 1240 Exam 1 May 29, 2012 Please print your name: M g :2 Access ID: Please CIrcle your TA’s name Ahmed Dhanusha Enc And the day you have quiz section Mon Tues Thurs Multiple choice (4 pts ea) :1 . \sNhat are the hybridizatiozzn of carbon atoms 1, 2, and 3 in the following? H QCZCH-CH3 . p, sp, and sp (9 3p: Sp: and 5p: c. sp, sp, and sp3 d.spz, sp3, and sp3 1 2 3 2. How many pi bonds are present' In the following structué? HZC ZCH-C EN a. 1 b. 2 3 3. Which species is the strongest base in the following equilibrium? (pKa H20 = 15.7, pKa NH3 = 36) H20 + NHzn “**____.__ 0H - + NH3 a. H20 QNH; c.0H' d. NH3 4. Alkanes are characterized by the general molecular form la a. anm b. an2n @anm d. anm 5. Carbon atoms 1, 2, and 3 in the following structure are classified, respectively, as 1 H3C CH3 2 A—\ 3 CH3 Quaternary, secondary, tertiary b. quaternary, primary, tertiary c. quaternary, secondary, secondary d. tertiary, primary, secondary 6. Arrange the following isomeric alkanes in order of increasing boiling point I. n-heptane ll. 2,3-dimethylpentane Ill. 2,2,3-trimethylbutane a.l<ll<lll b.ll<lll<l c.|ll<|<ll .l|l<ll<l 7. The most stable conformation of the compound shown has a. all methyl groups equatorial 1 CH3 b. equatorial methyl groups at C-1 and C-2, axial at C-4 c. equatorial methyl groups at C-1 and C—4, axial at C-2 GE e uatorial meth l rou sat C-2 and C-4, axial at C-1 J q - y 9 p H3O 4 2 CH3 8. What Is the hybridization of oxygen in alcohols? a. sp b sp2 @p3 d. none of these ‘ 32 Page 2 9. Which statement is correct concerning the relative stabilities of the two conformations, A and B, below? CH3 H __.__.‘-. H “HM ..__ m CH3 H CH3 A B a. A is more stable b. B is more stable QA and B are equal in stability d. A and B are not equal but the preferred conformation cannot be determined by inspection. 10. Rank the following alcohols in order of increasing reaction rate with HBr I. CH3CH2CHZCH20H 11- (CH3)3C0H m. CH3CH2(|3HCH3 OH a.ll<l|l<l b.lll<ll<l @l<lll<ll d.|<ll<ll| 11. (5 pts) What IS the IUPAC name of the compound to the right? ,s oi “(Vic (60740» 3 ~ H CH3cHCHZCHZC(CH3)3 55 67(1/MQ+/\:3 fie/MW OR 12. (5 pts) What is the formal charge on the carbon atom of the structure on the right? OH ..,| H— I—Q—I 13. (5 pts) What is the correct IUPAC name for the compound at the right? 5 7% Q MJLTJMW 14. (6 pts) Draw the most stable conformation of butane using the sawhorse form ,4 C143 /H (Ll-l g ('4' 1+ am7Ll' 29 CHM 1240 exam 1.docx ' 5/23/12 Page 3 15. (6 pts) Draw the line-bond structure for (CH3)3CCHZCH(CH3)2 H '.0'« l H u H"C"'C*“O""H ' st H 17. (6 pts) Using a chair form draw the most stable form of trans-1 ,2—cyclohexane H CH3 CH5 i H 18. (6 pts) Consider internal rotation about the C3-C4 bond of 2,3-dimethylpentane, shown on the right. Draw the lowest energy Newman projection about this bond. c143 H CH3 \ H 7" c&%x “ CHM 1240 exam 1.docx 5/23/12 Page 4 19. (6 pts) Draw the most stable chair form of this compound. CH(CH3)2 /::f W02 H; 20. (9 pts) Used curved arrows to show the mechanism in detail of the reaction of tert-butyl alcohol and hydrogen bromide. Include all of the steps and indicate if that step is fast or slow. CH3 Q14; CH3 «— + I . / —\l H kag ‘ u / ['4‘ l 1 ' -"' ,, d ch—C—Q—H + H-—-Br: H 36‘ v C 33. O + [Eff l . v” V ‘ \H CH3 CH3 lC/{S H— slow O)”; ' u #364 P‘bir @— HsC-wr + H’OM‘L I k? 14 \ CH3 cMS QHS CH3 ‘ ’ g//FT”" 96+ I ' I'lfic'l‘C/‘li’ +1 ; \_‘> l43CvC'Hg’k‘ C33 5&5 15 CHM 1240 exam 1.docx 5/23/12 ...
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