Set4 - Chem 210 Training Set IV Organic Chemistry Chem 210...

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Chem 210 Training Set IV Page 1 of 23 Organic Chemistry: Chem 210 Training Set IV The questions are arranged approximately in the order of the coverage of material in the lecture. This set covers the material of the final exam. Questions 1-50 cover the material of the typical makeup exam. Notes: I. When listing reagents, a slash (/) is used between reagents that are employed simultaneously, and a semicolon (;) is used between reagents that are employed in a stepwise fashion. II. The stereochemistry conventions are illustrated below: Br OH Br OH Br Br OH OH No stereochemistry shown Absolute stereochemistry shown Relative stereochemistry shown Absolute stereochemistry on one center, unspecified stereochemistry on the other III. Abbreviations: Me = methyl, Et = ethyl, Pr = propyl, Bu = butyl, Pe = pentyl, Ph = phenyl (i.e. benzene as a substituent), AcO = acetate (H 3 CCOO), MCPBA = m- chloroperbenzoic acid. 1 . The bond angle in H 2 O is: a) 109.5° because the oxygen is sp 3 and therefore tetrahedral. b) 120° because the oxygen is sp 2 and therefore flat. c) Slightly smaller than 109.5° because of increased s character in the lone pairs. d) Larger than 109.5° because the hydrogens want to avoid each other (steric). 2 . Which of the following contains at least one sp 2 carbon? a) I only b) I, II, and IV c) I, III, and IV d) II, III, and IV
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Chem 210 Training Set IV Page 2 of 23 3 . Which orbital of butadiene is involved in the following reaction with HBr? 4 . What are the formal charges on the three atoms of ozone in the resonance structure shown (in order from left to right)? a) 0, +1, –1 b) +1, 0,–1 c) -1, +1, –1 d) 0, 0, –1 5 . Which of the following is not a resonance structure of the others? 6 . Which of the following has the lowest barrier to rotation about the indicated bond?
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Chem 210 Training Set IV Page 3 of 23 7 . A four-bonded carbon atom uses two sp 3 and one sp 2 hybrids to make three bonds. What is the remaining hybrid that is used to make the fourth bond? a) pure s e) sp 3 b) pure p f) sp 4 c ) s p g ) s p 5 d) sp 2 h ) s p 6 i) cannot be determined without knowing the bond angles 8 . There are twelve constitutional cycloalkane isomers with a formula C 6 H 12 . What is the largest possible number of primary hydrogens in any of these isomers? a) 3 b) 4 c) 5 d) 6 e) 7 f) 8 g) 9 h) 10 i) 11 j) 12 9 . Which of the following conformations has the highest energy? 10 . What is the energy difference (in kcal/mol) between the two chair conformations of the following compound? a) 2.2 b) 3.2 c) 1.2 d) 0.6 11 . Which of the following equilibria has the lowest (smallest) G?
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Chem 210 Training Set IV Page 4 of 23 12 . Compound A is in equilibrium with which isomer at room temperature? 13 . One of the two chair conformations of cis -1-ethyl-3-methylcyclohexane is more stable than the other by 4.20 kcal/mol. What is the energy cost (in kcal/mol) of 1,3-diaxial interaction between an ethyl and a methyl group?
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This note was uploaded on 12/11/2009 for the course CHEM 210 taught by Professor Maslak,przemyslaw during the Fall '08 term at Penn State.

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Set4 - Chem 210 Training Set IV Organic Chemistry Chem 210...

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