Question

(C) Protonation of alkene to form a carbocation followed by addition of bromide ion (D) Addition of the proton to one face of the alkene with simultaneous delivery of a bromide ion from a different molecule of H-Br. 11. Which compound is the strongest nmucleophile for reaction of methane methanesulfonate (CHOS0.CH) in methanol at room temperature? (You may assume that everything is soluble in methanol) (A) potassium bromide (B) cesium iodide (C) sodiam chloride (D) lithium flaoride 12. Which proton is the most acidic? на но -Hp н 13. Which of the following molecules is impossible? (B) (C) (D) (A) 14. Which compound will have the lowest heat of hydrogenation? (A) (B) (C) (D) 15. Which alkene is the most stable? () ( (D) (A) Part I (45) Answer any five of the follewing nine questions. There is no penalty foe answering extra questions 1. Draw 1-(R)-3-(Sdichlorocyclohexane. Is this molecule chiral? Draw the molecule in its minimum energy conformation. Use a Newman projection 2. Provide reactions that would allow the following transformations to take place. You will need more than one step. There is more than one correct way to accomplish cach; just show one for each transfomation. You may use any reagents you need. -OH Br 3. Provide reasonable structures for the product of the following reactions. Pay attention to stereochemistry where it is important. If you expect enantiomers or diassereomers, indicate that fact clearly. Use wedges and dashes to indicate the stereochemistry when it is important ClHO DyPd

Answer 1

11. (B) Among the given metal halides cesium iodide is. mone ionic and also lodide has highest nucleophilicity. 12. He proton is more acidic . He proton is attached with more electronegative atom oxygen. which attract o-H bond electron towars it and makes the more acidic, 13. ( D o Penta valency of carbon is not possible as it has no vacant orbital 14. A tetra substituted alkene hars lowest heat O of hydrogenation . So the correct answer is cel