OLD+EXAM+2 - Q5 CH 18 Ethers epoxides 1(4pts If I want to...

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Q5 CH 18 Ethers, epoxides 1. (4pts) If I want to prepare isopropoxybenzene by alkoxymercuration/reduction, what must be the structure of my two organic starting materials? + 2. (4pts) What are the products of the following ether cleavage reaction: HBr + isobutoxybenzene + 3. (2pts) What is the missing product in the following reaction scheme? + 2(HBr) SH Br 2
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Q6 CH 19 Aldehydes/Ketones Predict the major expected product formed from 2-methylcyclohex-2-enone (the reactant shown for all 5 reactions) with each of the reagents indicated. Pretend that all reactions are irreversible. Draw your answers in the boxes provided. If no reaction is expected write “NR” in the box. 2pts each 1. (CH 3 ) 2 CuLi 2. H 3 O 1. CH 3 MgBr 2. H 3 O (Ph) 3 PCHCH(CH 3 ) 2 CrO 3 , H 3 O HOCH 2 CH 2 OH HCl O O O O O
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E2 CH 18, 19 1. Draw the following structures: (8pts) A) 2-ethoxypentane B) Isopropyl tert-butyl ether 2. Write out the IUPAC name for the following two structures: (8pts) A) O __________________________________________________ B) O H O ________________________________________________ 3. Which has the higher boiling point, diethyl ether or 1-butanol? EXPLAIN for full credit. (4pts) 4. Retrosynthesis. Show the best way to prepare methoxycyclopentane via Williamson ether synthesis ( ie., what two organic starting materials would you use?) (4pts)
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