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. A. 50 B. 35 C. 25 D. 5 2. Estimate the pK, of the proton indicated. OH A. 30 Β. 10 C. 5 D. 1 3. Identify the major product of the reaction shown. H H H H Br2 (in the dark) H Br Br Huy H H Br Br Br H B H A. B. C. 4. Identify the major product of the reaction shown. Br KO(CH)3 A. B. C. Page 3 Short questions Name 5. Which of the following terms is the best description of the alkene shown below. HO. (2 ① CI A. Cis Alkene C. Z Alkene B. Trans Alkene D. E Alkene 6. Which of the following is the most stable free radical? A. CF3 B. C. D. resonance! 7. Which of the following compounds are formed when ethene is bubbled into an aqueous solution of bromine and sodium chloride? Br₂/H2O/Nacl I. BrCH₂CH₂Br I. CICH₂CH₂Br I. BrCH2CH2OH A. I and II B. I and III C. II and III D. III and III 8. Which of the following reagents effectively cleaves carbon-carbon double bonds? A. Br2 and light B. meta-chloroperoxybenzoic acid C. OSO, follwed by H2O2 D. Q3 followed by (CH3)2S Page 4 Short questions Name 9. Ozonolysis of an unknown compound gave CH₂O, CH3CHO and CH3COCHO. What are possible structures for the unknown compound? CH₂O, CH3COCHO CH₂O, CH3COCHO 1. CH3CHO IV. CHECHO II. A. I and II B. I and IV C. II and III D. II and IV 10. Which of the following reactions does NOT occur as shown A. CH₂C C Na + CH3CO₂H CH3CO₂ Na + CHC CH B. CH3C C Na + CH₂OH CH₂O Na + CH3C CH C. CH₂C CH + NaNH2 NH3 + CHCC Na+ D. CH3C CH + NaOH H₂O + CHCC Nat 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? Potential energy J A. K is formed faster and is more stable than L. B. K is formed faster and is less stable than L K L C. L is formed faster and is less stable than K Reaction coordinate D. L is formed faster and is more stable than K Page 5 Short questions Name 12. Label the following pairs of molecules as E (enantiomers), D (diastereomers), or S (same molecule). Page 6 Long questions (Points as shown) Name 13. (16 points) For the following compounds, indicate whether they will react under SN1 conditions (EtOH, A), SN2 conditions (KI/acetone), both, or neither. Indicate the products and by which mechanism they are produced.