EXAM 2 review-key - O Br Li pentane CuI 9 Identify the...

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Exam 2 Review CEM 251 recitation [email protected] 1. Predict the products of the following reactions. Indicate regiochemistry or stereochemistry where relevant. 1. BH 3 2.H 2 O 2 , -OH HI 1. Hg(OAc) 2 2. NaBH 4 1. OsO 4 2. NaHSO 3 Br 2 H 2 /Pd 2. When 2,2-dimethyl-4-pentene-1-ol is treated with aqueous Br 2 , a cyclic bromo ether is formed rather than the expected bromohydrin. Propose a mechanism, using curved arrows to show electron movement. O Br Product
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3. Fill in the missing starting materials and reagents. Br Br Br OH OH OH 4. How would you make the following products? O O H ? ? ? ?
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5. A compound with the molecular formula C 30 H 50 Cl 2 has only one ring. How many Π bonds are in the structure? 6. How man chirality centers are present in the molecule? 7. Complete the following equations by drawing appropriate structures in the boxes (show all carbons and hydrogens and location of (+) charge clearly): HCl initial carbocation intermediate more stable rearranged carbocation product
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8. Predict the product(s) of the following reactions: OH HBr(xs) ether NBS CCl 4 OH SOCl 2 Br Mg ether ? H 2
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Unformatted text preview: O ? Br Li pentane ? CuI ? 9. Identify the reagents in the following scheme: OH Br OH Br OH Br OH Br OH Br A B C D 10. Use the above structures to answer the following questions: a. Which one of the structures is (1S,2R)-2-bromocyclohexanol? b. Which is the enantiomer of A? c. Which one is identical to: OH Br 11. What is the product(s) of the following reactions. Include stereochemistry where needed. OTs H 2 O Ethanol Cl NaCN CH 3 CN Br NaOAc H 2 O Br NaI DMF 12. Draw the appropriate products: Br ∆ , KOH an E 2 reaction Br ∆ , KOH an E 2 reaction Br CH 3 CH 2 NH 2 a first order reaction + carbocation intermediate major elimination product major substitution product 13. Draw the structure of the major substitution products of the following reactions Br H 2 O (an S N 1 reaction) NaCN (an S N 2 reaction) 14. Complete the synthesis: A B HO C D OH 15. Synthesize the following compound from acetylene and any alkyl bromide. OCH 2 CH 3...
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EXAM 2 review-key - O Br Li pentane CuI 9 Identify the...

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