Exam 1 Review Key

Exam 1 Review Key - Chemistry .241 Spring 2009 Mike Holden...

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Unformatted text preview: Chemistry .241 Spring 2009 Mike Holden Reptar! The world’s best dinosaur toy... .from the great old show, Rugrats (not the new show, but the old one, when you were little). Join me in a tribute to a classic cartoon and, by the way, you have 55 minutes to complete this exam. Good luck! Part 1. Multiple Choice (15 X 5 pts) 1. Which of the following structures are resonance structures of each other? H30 ' H30 H30 4. 4— \ /C—CH=CH2 C=CH-—CH2 /CH-CH=CH2 H30 . H3C H2C+ A B C a A and B . B and C C. All are resonance structures. D. None of these are a resonance structure. 2. Which of the following molecules are polar? (3ch1 eager; 001., A. B C A. A is polar. B. B is polar. C is polar. D A and B are polar. E. B and C are polar. 5. From the list below, which is the conjugate base of methanol? @ CHso- B. CH3' 0. CH50H2+ D. CH4 4:. Which of the circled hydrogens is the most acidic? H Chuckie Finster - afraid of nearly everything, he once had to deny that he was afraid of oatmeal. Technically, he said, he was just afraid of the picture of the guy on the front of the Quaker Oatmeal box. 5. What should go in the box on the right side of the equation? Hgso.I + NH; A. H3804 + + NH2 ' . H804 * + NH4 ‘ H804 ' + NH4 + . H2804 + NHS E . None of the choices are correct. 6. Which of the following statements is (are) true about compound A‘? i? if CHZCHZCHz—C—CH2CH2—C—H A A. Compound A is an ester. B C . Compound A is an aldehyde. . Compound A contains an aryl group. D. (Compound A is an ester) and (Compound A is an aldehyde) are true. CE) (Compound A is an aldehyde) and (Compound A contains an aryl group) are true. '7. Which of the following statements is (are) true about compound A? OH A A. Compound A is an alkene. B D E. . Compound A is an alkyl halide. . Compound A is an'alcohol. Both (Compound A is an alkene) and (Compound A is an alcohol) are true. Both (Compound A is an alkyl halide) and (Compound A is an alcohol) are true. Tommy Pickles is the main character in “Rugrats.” Although he is the youngest character, he is the leader of the gang of babies. Tommy carries a set of screwdrivers in his diapers to help with escapes from the crib. 8. Give the IUPAC name for the following compound. /\/ ‘ 4—isobutylyl—2-methylhexane @ 4-isopropyl—S-methylheptane C. 4-isopropyl—2-methylheptane 9. Select the most stable conformer of l, 5—hexane diol. OH OH OH OH HOEQ/OH \Y Y OH \/ —-\ A B. C A. A B . C D. D E. E 10. How are the molecules below related to each other? CH3 CH2 Elf and Cf ® They are constitutional isomers. B. They are identical. ‘ C. They are resonance structures. D. They are not isomers; they are different compounds. E. They are stereoisomers. Angelica Pickles, Tommy’s cousin, was rich and spoiled rotten. The oldest of the kids, she was the only character who could talk to both the adults and the babies. l l. Designate the following compound as R or 5'. A O 635 2 5 Phil and Lil DeVille are E 4 > unidentical twins. They do lots of disgusting l 5. R—Z-pentanol and S—2—pentanol are different with respect to their things — for instance, they like to eat dog food and worms (which they call “chocolate spaghetti”). A. boiling point and melting point. V B melting point. direction of rotation of plane-polarized light. D. number of degrees of rotation of plane-polarized light. Part II. Short answer. Answer the following. Any explanation need not be more than a sentence or two. 1. (a) (6 pts) Draw, in a chair configuration, cis-l-ethyl-2-methylcyclohexane. W" AEZ W) (b) (6 pts) Draw the “ring-flipped” conformer for the above compound. 0*) VA» (A) (c) (5 pts) Which of the above is more stable (if either)? In a sentence or two, why? 7') SM’JLV’ Sn”? L“GH’3\ .5 £1ug+lnb‘ 2. Consider butane. a. (6 pts) Draw a Newman projection that clearly indicates the most stable conformation of butane. 014 3 :4 " H H “‘3 b. (6 pts) Draw a Newman projection that clearly indicates the least stable conformation of butane. W H \ u H- 4. ('7 pts) (a) Draw the mechanism of the acid base reaction between water and hydrobromic acid. Label the acid, base, conjugate acid and conjugate base. Remember that it is an equilibrium! ' - '+_~6r ————-§ 9 [4,044 +- ( H -0 ~ :4 <—-’ u " M L3 3 A (5 pts) (b) Using the attached pKa chart, determine which direction is preferred for the above acid/base reaction. Explain your answer. —————» H-6r \{ 4 5W 491 m... H309 -'. Mm Spike is Tommy’s dog. He was good for always managing to get Tommy (and Chuckie) out of trouble at the last moment. Tommy rides him like a horse. 6. (6 pts) Draw all reasonable resonance structures for the following: 6 6 5. a. (6 pts') Draw a meso form of l,2-dibromo-1,2-dichloroethane. Label the stereooenters in your molecule as (R) or (S). cc £6 82 M n («a/KW» ,. <s> 9 r r b. (4 pts) Draw a diastereomer of your molecule in part (a). Label the stereocenters in this diastereomer as (R) or (S). o. (5 pts) Is your molecule in part (b) a meso compound? Why or why not? 95‘. 110* u no m-l‘VN-l flam- 6 {jam}? '7. (3 pts) Label each of the carbons below with its hybridization state. Angelica’s doll, Cynthia. Cynthia had many adventures, including being temporarily lost in a 1 1 . sewer, and once ‘ , ' Angelical faked ‘_ ' 3 Cynthia’s kidnapping ‘5 f S f in a plot to get more candy. ...
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This note was uploaded on 03/10/2010 for the course CHEM 241 taught by Professor Crouch during the Spring '08 term at Dickinson.

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Exam 1 Review Key - Chemistry .241 Spring 2009 Mike Holden...

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