5.12 Prof. B. Imperiali Practice Exam #3 Exam will be held Monday April 14th at noon. Notes and calculators will not be allowed in the exam but you will be provided with a periodic table and you may bring use molecular models to use. The exam will cover material from 3/12-4/11. The practice exam key will be posted as a separate file so that you can print up the exam and take it as a “real practice” before you check out the answers.Page 2 Short questions (1-9 3 points each and 10-12 4 points) 1. Estimate the pK, of the proton indicated. SG A.50 B35 (28) D.5 2. Estimate the pK, of the proton indicated. oS A.30 C5 D4 3. Identify the major product of the reaction shown. 4 . MH 5 so Hg re = a s H (in the dark) Br Br Br Br - A B. Cc. "NK © Br oH 4, Identify the major product of the reaction shown. B. c.Page 3 Short questions Name 5. Which of the following terms is the best description of the alkene shown below. HO. oO A. Cis Alkene B. Trans Alkene Cl F. © C.ZAtkene Alkene © 6. Which of the following is the most stable free radical? A CFs B. © Ce D. CT resonance | 7. Which of the following compounds are formed when ethene is bubbled into an aqueous solution of bromine and sodium chloride? Br, /H,o (N2ck |. BrCH,CH,Br 1. CICH,CH,Br |. BrCH,CH,OH A. land It B.1and til C. Wand til (jan and Ill 8, Which of the following reagents effectively cleaves carbon-carbon double bonds? A. Br, and light meta-chloroperoxybenzoic acid C. Os0, follwed by H,0, followed by (CH,)SPage4 Short questions Name 9. Ozonolysis of an unknown compound gave CHz=0, CHsCHO and CH;COCHO. What are possible structures for the unknown compound? Oh0, cn,cocHo CHO, cHcOcHo , 1 euscHo x x* CHSENO L ~~ u > “KX “OK. A. land Il (paw C. land Ill D.IandiVv 10. Which of the following reactions does NOT occur as shown “A. CHjC=C'Nat + CHjCOH ——® CH,CO,Na* + CH,C==CH “B. CH,C=C'Na* + CHOH = —® CH,O'Na* “@. CHC=CH + NaNH, — > Hs 11. Compound J undergoes a rearrangement to yield compounds K and L. Based on the potential energy diagram below which of the following statements is true? =CH + NaOH —_— H,0 + CH,C==cNa* A. K is formed faster and is more stable Potential than energy J B. K is formed faster and is less stable than L C. Lis formed faster and is less stable K than K L (2) is formed faster and is more stable - - dn Kk Reaction coordinatePage 5 Short questions Name. 12. Label the following pairs of molecules as E (enantiomers), D (diastereomers), or S (same molecule). Br Br 38 CHsPage 6 Long questions (Points as shown) Name ee 13. (16 points) For the following compounds, indicate whether they will react under Sy1 conditions (EtOH, A), Sy2 conditions (Kl/acetone), both, or neither. Indicate the products and by which mechanism they are produced. Syl Sat H.C. CH, a at con ane Se ° orou H yee, os Bo oat Lar Sat TD sar eee) v H;CO™ “Cl r 2 as sco" el BLE Q & OCH, t ont a, ae — nok a pood & Liq.Page7 Long questions (Points as shown) Name. 14. (20 points) Design syntheses of compounds | and II (10 points each). The pool of carbon-containing starting materials that you can use are shown in the square brackets. You may use any other common reagents. nL HY io XN bo lo OH 2] PABaSo, —_ Lindla's eab inn Rewesyw Sak A Note: a clear retrosynthetic analysis will be useful for figuring these problems out. Partial credit will be given for a retrosynthetic analysis even if the synthesis is incomplete. Orinn, QO wnee Syahests: weese- nt ——» We Orns. re Qe arPage 8 Long questions (Points as shown) Name 15. (24 points) Provide a detailed stepwise mechanism to account for the following transformations. 8 points each. a. Cie u Nat OMe eB ~. fg J nee Lee x woke xe woe Lake Sy1 conditions iv oy Lae rls, ory Be # a