14D_w11_e02

14D_w11_e02 - Chemistry 14D Winter 2011 Exam 2 Page 1 OK to...

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Chemistry 14D Winter 2011 Exam 2 Page 1 Page 1 score = OK to use "Ph" anywhere on this exam where appropriate. Questions 1–3 refer to the manufacture of chloroprene. Chloroprene is polymerized to make Neoprene, a synthetic rubber material found in (among other things) diving suits. At one time chloroprene was manufactured by the reaction of vinyl acetylene with HCl. 1. (2) Circle the most likely structure for chloroprene, i.e., the most likely product of this reaction: C C HCl Cl H or Cl or C C Cl 2. (2) Does the addition of HCl to vinyl acetylene obey Markovnikov's rule? Circle one: Yes No Markovnikov's rule does not apply in this case 3. (2) Chloroprene can also be produced by reaction of 1,3-butadiene with Cl 2 , followed by an E2 elimination of HCl. Draw the structure of the missing molecule (whose formula is C 4 H 6 Cl 2 ) in the box. Cl 2 Strong base Chloroprene C 4 H 6 Cl 2 4. (10) Write a reasonable mechanism for the following reaction. H 3 C H 2 SO 4 H 2 O H 3 C OH 5. (2) Circle the correct statement concerning the position of this equilibrium: Ph CH 3 Ph CH 3 OH O K eq < 1 K eq very nearly = 1 K eq > 1
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Chemistry 14D Winter 2011 Exam 2 Page 2 Page 2 score = Questions 6–8 refer to this reaction: C C H H 2 SO 4 H 2 O O H + CH 3 O Molecule A Molecule B 6. (1) The major product of this reaction is (circle one): Molecule A Molecule B 7. (10) Write a mechanism for the formation of the product that you circled. 8. (3) Complete this explanation by adding no more than twenty words : This is the major product because. .. 9.
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14D_w11_e02 - Chemistry 14D Winter 2011 Exam 2 Page 1 OK to...

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