Organic Chemistry I Exam 1

Organic Chemistry I Exam 1 - NAME Soc Sec Intro Organic...

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Unformatted text preview: NAME Soc Sec # Intro Organic Chemistry 030.104.01 (0'30. 2053 Dr. K‘ein EXAM 1 Summer Session 1 June 20, 2003 CHOOSE ONLY ONE ANSWER FOR EACH PROBLEM 1) Which drawing best represents the shape of an sp3 hybridized orbital? 3) 2) What is the hybridization state for the carbon atom in formaldehyde? 80 SP3 b) 8132 c) Sp d) p 3) Identify the number of carbon atoms in the compound below: / ¢. a) 13 b) 14 c) 15 d) 16 4) Identify the number of hydrogen atoms in the compound above. a) 14 b) 16 c) 18 d) 19 5) Identify the number of carbon atoms with trigonal planar geometry in the compound above. a) 4 b) 6 c) 8 d) 10 6) True or False: The difference in energy between a pi bonding molecular orbital] and a pi antibonding molecular orbital is GREATER than the difference in energy between a sigma bonding molecular orbital and a sigma antibonding molecular orbital. a) TRUE b) FALSE 7) Choose the drawing below that displays the appropriate formal charges: (9 . «0/ 00/ v . / 9/ 1 ‘o 'o NOH N53 C) NEH d) we? a) ' ' b) ‘ 8) How many lone pairs does the nitrogen below have? (IN: 1 a)0 b)l c)2 d)3 9) The geometry of benzene is best described as: E) a) planar b) tetrahedral c) a chair d) a boat 10) Consider the curved arrow below, and select the sentence that best describes it. 00- M a) This arrow violates the first commandment of drawing resonance structures b) This arrow violates the second commandment of drawing resonance structures 0) This arrow violates both commandments of drawing resonance structures d) This is a perfectly good arrow for drawing resonance structures 11) True or False: Resonance structures represent an equilibrium process between two different compounds. a) TRUE b) FALSE 12) Consider the compound shown below: OH (5 A resonance structure of this compound is: (*3 8H CH 8H . be b 9:: ~ a) b) 9 c) d) all of the above 1 13) True or False: When you have four different groups attached to a carbon atoi11, there are exactly 4 different ways to arrange those groups in space. 1 a) TRUE b) FALSE 14) Choose the drawing below that is not a resonance structure for nitroethylene 9 ”$140 flfi/O /\e 0 ”N40 H II a) 09 b) O c) 09 d) O 15) True or False: @ /\/ 9 is a significant resonance structure for trans-Z-butene. a) TRUE b) FALSE 16) In the following compound, describe the nature of the lone pairs: I NVOH /\g/ a) the lone pairs on the OH are delocalized, and the lone pair on the nitrogen is localized b) the lone pairs on the OH are delocalized, and the lone pair on the nitrogen is delocalized c) the lone pairs on the OH are localized, and the lone pair on the nitrogen is localized d) the lone pairs on the OH are localized, and the lone pair on the nitrogen is delocalized 17) Consider the compound below: The parent for this compound is: a) hept b) oct 0) non d) dec 18) Consider the compound below: Ho/fifH O The suffix of the name of this compound is: a) —oic acid b) —one 0) —al (1) —01 19) Select the name of the following compound: /\(\I/ a) E-3,5-dimethylhex—2-ene b) E-2,4—dimethy1hex-4—ene c) Z—3,5—dimethylheX-2—ene d) Z-2,4-dimethylheX-4-ene 20) Choose the drawing below that will have the following name: 2,2-dichloro-4,4-dimethyl-hept-6-en-l-ol CI HO \ C! Cl W M Cl Cl CI CI H M \/\/\)</\ C) 0 \ d) HO / 21) Consider the energy diagram shown below: The gauche interactions occur in a) structures 3 and 5, b) structures 2 and 6, c) structure 4, (1) structure 1 22) True or False: Staggered conformations are generally lower in energy than eclipsed conformations. ‘ a) TRUE b) FALSE 23) Consider the substituted cyclohexane shown below: \\“‘ Thetwo chair conformations for this compound are: 20% fl mglfl 0) er he 5t 24) Which of the following chairs is more stable: by 13% gm 09w 25) True or False: The enantiomer of A is B. (EV ‘ / \\“" D "’II/ A B l a) TRUE b) FALSE Cl 1 26) When the following chair ; undergoes a ring flip, the new chair looks like this: . , 1 m 0'? J | a) Cl b) 0) Cl d) Cl 27) Consider the compound below: HO/E l ,OH NH2 0 The most acidic proton in the following molecule is: an Wham a) NH2 0 b) NH2 0 28) From the group of compounds below, choose the most acidic compound: a) #1 b) /\/ c) W d) NH2 0 I— 29) Which side of the reaction does the equilibrium favor in the following reaction: 9 e H’O‘H + CH3O =:—=HO + CH3OH a) the right side b) the left side 1 c) both sides equally 1 (1) cannot tell without more information 1 OH 30) True or False: the mechanisms of all acid base reactions look like this: Base/EX a) TRUE b) FALSE l 31) Place the following in order of stability: (fr Cd fr if 1 2 3 4 a) l > 2 >' 3 > 4 (where l is the most stable) b) 1 > 3 > 2 > 4 (where 1 is the most stable) c) 4 > 1 > 3 > 2 (where 4 is the most stable) (1) 2 > 3 > 4 > 1 (Where 2 is the most stable) 32) In a mechanism, curved arrows represent the flow of l a) electron density b) atoms c) molecules d) all of the above, depending on the situation 33) Consider the following compound: cu,“ "”11 How many stereocenters are there? a) 4 b) 5 c) 6 d) 7 34) How many stereoisomers can be drawn of the compound above (Problem #313): a) 32 b) 31 ' c) 64 d) 63 1 35) The compound above (problem #33) has how many enantiomers? a) 0 b) 1 c) 64 d) 63 36) Consider the following compound: Cl: Br H , t O The configurations of the stereocenters in the compound above are: a) 2R, SS b) ZS, 5R c) ZS, 5S d) 2R, SR 37) Consider the compound shown below: OH /\‘/Y\/ The enantiomer of this compound is: CH 9H a) b) 5 0) OH (1) all of the above 38) The following two compounds are: n or a) Diastereomers b) Enantiomers c) The same compound (1) Different compounds that are not stereoisomers at all 39) The following two compounds are: a) Diastereomers b) Enantiomers c) The same compound (1) Different compounds that are not stereoisomers at all 40) Do you expect the following to be optically active? Cl CI M a) Yes b) No c) It depends on the temperature (1) Cannot tell without actually trying it in the lab 41) True or False: A racemic mixture of enantiomers is not optically active a) TRUE b) FALSE 42) Hyperconjugation is an effect that describes the overlap of a) two p orbitals b) two sp3 hybridized orbitals c) a hybridized orbital and a p orbital d) all of the above 43) Name the following compound: (6 points) NAME 44) Draw one resonance structure for each of the following compounds. Show your curved arrows. (2 points each) ...
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