SampleExam2 - aldol products. OH CHO O 17. Provide starting...

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Page 1 of 4 CHM 2220 Sample Exam Questions 1. Rank the indicated protons in terms of acidity using the number 1 to 4. Label the most acidic proton(s) 1 and the least acidic proton(s) 4. O H H O HO H O O OH H H 2. Draw the major enolate formed in each reaction. O NaOEt EtOH 25 o C O LDA / THF / -78 o C Write the major organic product formed in the following reactions. 6. CO 2 H OH H 2 SO 4 7. warm reaction to 50 o C CHO NaOCH 3 2
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Page 2 of 4 8. Br 1. Mg 2. CO 2 3. H 3 O + 9. O HO O heat 10. OCH 3 O H 3 O + 11. Cl O OH O 12. OH O OH H + 13. O O O OH H + 14. N(CH 3 ) 2 O CH 3 OH
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Page 3 of 4 15. O O O NH 2 16. Provide starting materials for each of the following
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Unformatted text preview: aldol products. OH CHO O 17. Provide starting materials for each of the following products formed by Robinson annulation . O O Page 4 of 4 18. Fill in the boxes with the appropriate structures. (3 points each box = 18 total) Br NaCN LiAlH 4 (CH 3 CO) 2 O H 2 SO 4 H 2 O heat CH 3 OH H + LiAlH 4 Compound pKa H 3 O +- 1.7 HNO 3- 1.4 HF 3.1 (CH 3 ) 2 NH 2 + 4.6 CH 3 COOH 4.7 2,4-pentanedione 9.0 HCN 9.1 NH 4 + 9.4 H 2 O 15.7 acetone 19 CH 3 C= CH 26 NH 3 36 (CH 3 ) 2 NH 36 CH 4 60...
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SampleExam2 - aldol products. OH CHO O 17. Provide starting...

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