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06 Question (4 points) e See page 574 Complete the mechanism. All necessary atoms and bonds (that is, those that are involvede See pa 09 Question (4 points) Predict the organic starting material needed to prepare the following geminal dibromide upon18 Question (4 points) Hoping to synthesize 3,3-dimethyl-2-butanol, an inexperienced student reacted 3,3-dimethyl-1-butene wiPLEASE SHOW ALL WORK AND PLEASE ANSWER ALL PARTS OF EACH QUESTION! Thank you!

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: 8-6 All necessary atoms, and bonds are drawn. We have to Just add the missing curred arrow notation in the structures (provt excess HBr. Mechanism proposed ch Concerted step. ? Bir Hydrobromination .. of alkene Hiery M t ... (2 carboeation.) I nTop****sob 2° carbocation). Less stable) 3 shift. (3 carbocation) . OH more stable). : (2,3 dimethyl-2-butanol) Alkene takes up

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