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2 I. Predict which compound will be more acidic. Explain your answer with structures. (6 pts) 3-Florobutan-1-ol vs 2-Florobutan-1-ol II. What carbonyl compounds and Grignard reagents would you use to make the alcohols shown below? Show all possibilities. No mechanism necessary. (8 pts) a. HO OH b. 3 III. Draw the mechanism and predict the products of the following reactions. (10 pts ) a. 1. 2 LiAlH4 2. H3O+ O O b. 1. 2 CH3CH2MgBr 2. H3O+ O OCH3 IV. Give the structures of the intermediates and products A through E. No mechanism necessary. (10 pts) SOCl2 A Mg, ether B CrO3, H+ C 1. C 2. H+ D O Cl 2-Butanol E 4 V. How would you synthesize the product from the given reactant in the following reaction? Show the reaction scheme of each step. No mechanism necessary. (10 pts) OH multisteps a. Br multisteps b. VI. How would you confirm the following reaction using IR spectroscopy? (5 pts) And find the number of peaks in 1H-NMR spectra for both compounds. (3 pts) Cl OH O 5 VII. Sketch the 1H-NMR spectra of the following compounds. Assign peaks to the structures. Indicate a peak in the most de-shielding region from each compound. (10 pts) a) CH3CHCH2COCH3 O CH3 b) Br CH2CH3 6 VIII. Determine the structure of the compounds below from their spectroscopy data. Assign peaks to the structures. (12 pts) a) b) C4H7BrO 2.11 (3H, singlet) 3.52 (2H, triplet) 4.40 (2H, triplet) chemical shift (ppm, peak position) integration splitting C4H10O 7 IX. The reaction schemes shown below are the Williamson ether synthesis and the acidic cleavage reaction of ethers. Fill the boxes to show how you would prepare the following ether and the acidic cleavage reaction of the ether under the strong acidic. (6 pts) + NaH HBr O

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