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o ADDITIONAL PROBLEMS 3.15 What is the conjugate base of each of the following acids? (a) NH, (d) HC=CH (b HO (e CHOH (9H 3.16 Listthe bases you gave as answers to Problem 3.15 in order of decreasing basicity. CHAPTER 3. AN INTRODUCTION TO ORGANIC REACTIONS: ACIDS AND BASES 317 What is the conjugate acid of each of the following bases? (a) HSOS (d) NH; (b) HO (e) CH.CH; (0) CH;NH, — (f) CHICO; 318 Listthe acids you gave as answers to Problem 3.17 in order of decreasing acidity. 3.19 Designate the Lewis acid and Lewis base in each of the following reactions: 1 (a) CH,CH;—CI + AICI, —» CH;CH;—CIAI=CI a F | (b) CH—OH + BE, —» O HF cH, H, (9) CE" + HO — CH (0H CH, CH, 3.20 Rewrite each of the following reactions using curved arrows and show all nonbonding electron pairs. (a) CH,OH + HI—» CH,OH,* + 1º (b) CH,NH; + HCI—» CH;NHy + CIO H H HH Seas La (9 Je=C0 +HE=>+H-CoC=H+RO H H k 321 When methyl alcohol is treated with NaH, the product is CH,O Na (and H,) and not Na* “CH,0H (and Ho). Explain why this is so. 327 What reaction will take place if ethyl alcohol is added to a solution of HC=C: “Na* in liquid ammonia? 3.23 (a) The K, of formic acid (HCO, H) is 1.77 x 1074, What is the pK,? (b) Whatis the K, of an acid whose pk, = 13? 324 Acid HA has a pk, = 20; acid HB has a pK, = 10. (a) Which is the stronger acid? (b) Will an acid-base reaction with an equilibrium Iying to the right take place if Na A“ is added to HB'? Explain your answer. 325 Write an equation, using the curved-arrow notation, for the acid-base reaction that will take place when each of the following are mixed. If no appreciable acid -base reaction takes place, because the equilibrium is unfavorable, you should so indicate (a) Aqueous NaOH and CH,CH;CO,H (b) Aqueous NaOH and C,H,SO,H (e) CH,CH,ONa in ethyl alcohol and ethyne (d) CH,CHsLi in hexane and ethyne (e) CH.CH,Li in hexane and ethyI alcohol ADDITIONAL PROBLEMS 3.26 Show how you would synthesize each of the following, starting with an alkyl bromide and using any other needed reagents. (a) CH,;CH,CH,D (b) CH,CHDCH, (e) fts CHG=D cH, 3.27 Starting with appropriate unlabeled organic compounds show syntheses of each of the following: (9) CH—CEC—T (b) CH—CH—O-D (0) CHyCHsCH;OD CH, 3.28 (a) Arrange the following compounds in order of decreasing acidity and explain your answer: CH;CH,NH,, CH,CH,0H, and CH;CH,CH,. (b) Arrange the conjugate bases of the acids given in part (a) in order of increasing basicity and explain this answer. 3.29 Arrange the following compounds in order of decreasing acidity: (a) CH;CH=CH,, CH.CH,CH,, CH;C=CH (b) CH;CH,CH,0H, CH,CH,CO,H, CH,CHCICO,H (c) CH;CH,0H, CH,CH;0H;*, CHOCH; 3.30 Arrange the following ions in order of increasing basicity: (a) CH;NH,, CH;NH;*, CH;NH” (b) CH,O-, CH,NH”, CH.CH,- (c) CH;CH=CH”, CH,CH,CH;", CH;C=C- 3.31 Whereas H;PO, is a triprotic acid, H;PO, is a diprotic acid. Draw structures for these two acids that account for this difference in behavior. 3.32 Supply the curved arrows necessary for the following reactions. 
