EXAM_1_2007 - 1 1) (6 Points, 2pts. each) Give the correct...

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Unformatted text preview: 1 1) (6 Points, 2pts. each) Give the correct IUPAC name for the following structures: Br H3CH2C H CH2CH2CH3 Cl a) H3C b) CH3 Include cis/trance c) Cl Cl 2) (6 Points, 2pts. each) Give the correct structure for the following names: a) (Z)-3-chloro-5-fluoro-4-nonene b) 1,3,5-Cyclodecatriene c) 1,6-diethylcyclohexene 2 3) (6 pts.) Draw the Gauche and Anti conformation for 1,2-dichloroundecane looking from C4 to C5 in the appropriate boxes. Gauche Conformer Anti Conformer 4) (6 pts. 3pts. Each) Predict the position of equilibrium in the following acid-base reactions by circling the favored side. a) HCN + CH3COO– CH3COOH + CN– pKa = 4.76 pKa = 9.31 b) CH2CH3C pKa = 25 CH + NaH CH2CH3C CH + H2 pKa = 40 5) (6 Points, 3pts. Each) Draw the Lewis dot formula for ozone, O3 and write a resonance structure for it. 3 6) (6 Points, 2 pts. Each) What is the relationship between each pair? Your choices are: Constitutional isomers, Configurational isomers, Conformational isomers or Identical. Br Br Br Br Br Br Br Br Br Br Br Br Br Br a) b) c) Br Br Br Br 7) (10 pts.) Answer the following questions about Compound A. O C NCH3 ComPound A SCH2CH3 a) Which of the atoms in Compound A is the most electronegative atom? b) What is the hybridization of the nitrogen in Compound A? c) What is the hybridization of the sulfur in Compound A? d) How many p–electrons are there in Compound A? e) How many SP– hybridized atoms are there in Compound A? 4 9) (5 Points) Which of the following compounds is the most stable one? A B C D 10) (5 Points) Draw five constitutional isomers for cyclic compounds with the molecular formula of C6H12. 5 11) (12 Points) For the following reaction: Br2, H2O a. (3 pts.) Give the major organic product in the box provided above. b. (3 pts.) Draw the structure of the fastest formed (most stable) reaction intermediate for the above reaction. c. (6 pts.) Draw an energy diagram (reaction coordinate diagram) for the above reaction assuming an exothermic reaction. You must clearly indicate the position of reactants, products, transition state(s), change in Gibbs free energy, activation energy, and carbocation intermediate. 6 12. (33 pts.. 3 pts. Each) Fill in the boxes with the appropriate reactants, reagents, or products. For the products, only draw the major organic product. Note: Make sure to show stereochemistry where appropriate. CH3 a) Cl2 Stereochemistry CH3 b) HBr O Ph O O O Ph c) H3CHC CH2 hn CH2 d) 1. Hg(OAc)2 H2O 2. NaBH4 e) H2 Pt Stereochemistry 7 CH3 f) 1) O3 2) Zn, HCl g) 1) OsO4 2) NaHSO3 Stereochemistry HIO4 CH3 h) 1. BH3 2. H2O2, OH Stereochemistry i) H2O H There are two products for this reaction, one of hich is a rearragement product. Rearrangement Product ...
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This note was uploaded on 03/29/2008 for the course CEM 251 taught by Professor Rathke during the Spring '07 term at Michigan State University.

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