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2 CAS C 203 Exam 2 rganic Chemistry 4 November 2010, 8:00 A.M. 9:20 A.M. Name D Number nstructions (A) Make sure you have 5 pages with 7 questions. (B) Write all answers on the pages provided. (C) nly answers written in ink will be considered for regrading. (D) Good luck! V V V V V e Li Be B C N F Ne Na Mg Al Si P S Ar K Ca Ga Ge As Se Kr Rb Sr n Sn Sb Te Xe Page Score 1 /14 2 /32 3 /21 4 /21 5 /12 Total /100
3 page 1 (1a) 1,3-Butadiene can be prepared by the reaction of vinyl chloride with ethylene: + + vinyl chloride ethylene 1,3-butadiene Using data in the table, calculate the standard enthalpy change º of the reaction. Show your work and write your answer in the space provided. (5 points) º = = 14 º = 14 kcal/mol (1b) 1,3-Butadiene can also be prepared by the reaction of two ethylene molecules: Using data in the table, calculate the standard enthalpy change º of the reaction. Show your work and write your answer in the space provided. (5 points) º = (2 112) = +5 º = +5 kcal/mol (1c) Which reaction is more thermodynamically favorable, that in (1a) or (1b)? iefly explain the reason(s) for your choice. (4 points) (1a) is more favorable because its º is more negative. Bond Bond Dissociation Energy, D [kcal/mol] C 2 C C 2 C 112 C 2 C CC 2 115
4 page 2 (2) Draw the structure of the major organic product of these reactions and reaction sequences. n those reactions marked, clearly indicate the stereochemistry of the product. Do not present mechanisms. (32 points) 3 C C 3 3 C C 3 2 (a ) Pd C 3 (b) 3 C C 3 C 3 (1) g(ac) 2 2 (2) NaB 4 3 C C 3 C 3 (c ) (1) s 4 (2) NaS 3 (d) 3 C 3 C 3 C 2 gs 4 2 S 4 3 C 3 C 3 C C 3 C 3 (1) B3 C 3 (e ) (2) 2 2 Na (f) C 3 (g ) C 3 C 3 2 C3 C 3 (h ) 3 C RC C C C 3
5 page 3 (3) Write the systematic name of these compounds, including stereochemical designations where appropriate. (12 points) (a) C 3 7-chloro-2-methylcyclohepta-1,3-diene 3 C C 3 (b) (Z)-4-bromo-2,6-dimethyloct-3-ene 3 C C 3 (c) 3 C 3 C F (E)-3-fluorohept-2-en-5-yne (d) (E)-3,8-dibromoocta-1,3-dien-7-yne (4) Propose a detailed mechanism for this reaction; use curved arrows to show the movement of electrons. (9 points) C 3 C 3 + C 3 C 3 C 3 C 3 C 3 C 3 C 3 C 3
6 page 4 (5) α-phellandrene (C ), the sex-attractant of the Caribbean fruit fly Anastrepha suspensa, reacts with excess 2 in the presence of a Pt catalyst to produce Compound A; reaction with with excess 3 followed by work-up with Zn and C 3 C 2 produces Compounds B and C. Draw the structure of α-phellandrene in the box. (6 points)!-phellandrene C excess 2 Pt 3 C C 3 C 3 C 3 C 3 Compound B + (1) excess 3 (2) Zn, C 3 C 2 3 C Compound C Compound A 3 C C 3 C 3 (6) Propose a short sequence of reactions for transforming the indicated starting material to the target molecule. Draw the structure of the product formed after each reaction; do not write mechnisms. (15 points) (a) C 3 more than one step C 3 C 3 X X C 3 K C 3 RC 3 C 3 C 3 C addition, dehydration, then epoxidation also acceptable C 3 C 3 (b) 3 C C 3 more than one step 3 C C C C 3 3 C addition first, then 2 also acceptable C 3 3 C C 3
7 page 5 (7) Propose a detailed mechanism for these reactions; use curved arrows to show the movement of electrons. (12 points) (a) C (b) + C C + 3 C 2 2 C 3 C 3 +
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