CHAPTER 22 HW: CO 2 H DERIVATIVES

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1 CHAPTER 22 HW: C 2 H DERIVATIVES MECLATURE 1. Give the name for each compound (IUPAC or common name). Use R/S naming where needed. Structure Br ame Structure ame 2. Give the name for each ester. Structure ame 3. Give the name for each amide. Structure F F H H 3 C Br ame Page 1

2 4. Give the name for each compound, using cis/trans, E/Z or R/S naming where needed. Structure Br Br ame Structure F ame Structure I ame SPECTRSCPY 5. For each pair of isomers (A+B, then C+D), give two methods that IR spectroscopy can be used to distinguish between the isomers. Give specific wavenumbers where their IR spectra would differ. A H B C D 6. Acetic anhydride has two strong signals in its IR spectrum, at 1827 and 1755 cm -1. What do these signals specifically represent? Page 2

3 7. In each set are listed wavenumbers for the carbonyl stretching modes in each compound s IR spectrum. Explain in detail why in each set, one carbonyl absorbs IR at a higher wavenumber than the other. Hint: draw resonance structures. Acetyl chloride v = 1799 cm -1, Ethyl acetate v = 1743 cm -1 Butanoic acid v = 1717 cm -1, Butanamide v = 1660 cm Predict which carbonyl would absorb infrared radiation at a higher wavenumber. Explain in detail, using appropriate structures. 9. The 1 H MR of DMF has 3 signals at 2.93, 3.03 and 8.00 ppm. Explain why 3 signals are observed. H DMF Page 3

4 10. Predict the number of signals expected in both the 1 H and 13 C MR spectra of each compound. 1 H MR: 1 H MR: 13 C MR: 13 C MR: REACTIVITY TREDS 11. Explain the trends in reactivity toward nucleophilic acyl substitution, using appropriate structures with your answer. Acetyl bromide is more reactive than methyl acetate. Acetic anhydride is more reactive than methyl acetate. c. Ethyl acetate is more reactive than -methylacetamide. Page 4

5 ACID HALIDE AD AHYDRIDE REACTIS 12. Draw the curved arrow mechanism for each reaction. excess H 3 H 13. Give all organic and inorganic products of these reactions. H 2 e. H 2 H py. f. Ph Ph py. H c. Br CH3 CH 2 H py. g. d. h. excess CH 2 H Page 5

6 CARBXYLIC ACID REACTIS 14. Give the curved arrow mechanism for each reaction. + S H H H para-toluenesulfonic acid ( p-tsh) p-tsh H H 15. Give the major organic product of these reactions. H CH 2 H H 2 S 4 c. H H H 2 S 4 H Ph H cat. H + d. H H p-tsh 16. The Fischer esterification reaction does not always produce good yields. What specific methods can be used to drive the reaction to completion? Page 6

7 17. What reagents are needed to synthesize each compound using a Fischer Esterification reaction? ESTER REACTIS 18. Give the curved arrow mechanism for each reaction. KH H 2 H + H 2 S 4 H 2 H + H Page 7

8 19. Give the major organic product of these reactions. ah (aq) c. Et KH H 2 Ph H 2 S 4 H 2 d. p-tsh H Explain why ester hydrolysis using acid generally has an equilibrium constant of ~1, while ester hydrolysis using base has an equilibrium constant greater than Give the curved arrow mechanism for this reaction. MgBr H H +, H Complete the sequence by filling in the necessary reagents for each synthetic step. H H Page 8

9 CMBIED REACTIS 23. Give the major organic product of these reactions. H S 2 f. H H H 2 S 4 H 2 S 4 g. H 2 ah H 2 c. H 2 S 4 h. H CH 2 H H H 3C H H 2 S 4 d. S 2 H i. H p-tsh H e. ah H 2 j. H 2 S 4 H 2 AMIDE AD ITRILE REACTIS 24. Give all organic and inorganic products of these reactions. con. ah c. H 2 con. H + H 2 C con. H + H 2, heat d. C con. ah H 2, heat Page 9

10 25. Give the curved arrow mechanism for each reaction. con. ah H 2 + H 3 H con. H + H 2 H H 3 c. C con. ah H 2, heat + H 3 Page 10

11 26 continued d. C con. H+ H 2, heat H + H4 + HYDRIDE REACTIS 26. Give the major organic products of these reactions. Assume excess inorganic reagent in each. LiAlH 4 H +, H 2 f. DIBAL-H H +, H 2 LiAlH 4 H +, H 2 g. C LiAlH 4 H +, H 2 c. DIBAL-H H +, H 2 h. LiAlH 4 H +, H 2 d. C DIBAL-H H +, H 2 i. H LiAlH 4 H +, H 2 e. LiAlH 4 H H +, H 2 j. C DIBAL-H H +, H 2 Page 11

12 SYTHESIS 27. Devise a synthesis than converts 3-bromo-1-propene into 3-butenoic acid. Br H 28. Design a synthesis to perform the following transformations, showing all reagents and synthetic intermediates (no mechanisms are necessary). H Br H c. C 2 H C 2 H Page 12

13 d. H e. f. CH 2 H g. Page 13

14 h. i. Page 14

CHAPTER 22 HW: CO 2 H DERIVATIVES

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