Practice HW-OChem-II

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Practice HW Shabbir 320N Do Not Turn In 1 Q1 - Fill in the boxes with the products of the following reactions. Draw only the MAJOR product and indicate stereochemistry. If a 50:50 mixture of two possible products is formed draw both in the box. When a racemic mixture is formed, mark the chiral center with an asterisk (*) and write “racemic” in the box. Br 2 , FeBr 3 CH 3 Br, AlBr 3 H 2 CrO 4 H 2 SO 4 , SO 3 HNO 3 , H 2 SO 4 H 2 , Pd Cl O AlCl 3 1 Cl 2 , FeCl 3 , 2. NaOH 3. H 3 O + Br 2 , h ν HNO 2 HBF 4 KCN CuCN 1. LiAlH 4 2. H 3 O + O SO 3 H OH O NO 2 NH 2 N 2 + F CN NH 2 Br Br O
Practice HW Shabbir 320N Do Not Turn In 2 Q2- Fill in the boxes with the products of the following reactions. Draw only the MAJOR product and indicate stereochemistry. If a 50:50 mixture of two possible products is formed draw both in the box. When a racemic mixture is formed, mark the chiral center with an asterisk (*) and write “racemic” in the box. NH 2 CH 3 OH H 2 SO 4 OCH 3 NO 2 Br 2 , FeBr 3 NO 2 SO 3 , H 2 SO 4 CH 3 Cl NO 2 NaNH 2 1. H 2 , Ni, 2. HNO 2 3. H 2 O Cl O AlCl 3 NaOH CH 3 Br CH 2 PPh 3 OH Cl O O NH 2 Cl HNO 2 KI HNO 2 HBF 4 NaNH 2 CH 3 Br
Practice HW Shabbir 320N Do Not Turn In 3 Q3- Fill in the boxes with the products of the following reactions. Draw only the MAJOR product and indicate stereochemistry. If a 50:50 mixture of two possible products is formed draw both in the box. When a racemic mixture is formed, mark the chiral center with an asterisk (*) and write “racemic” in the box. AlBr 3 O HNO 3 Br 2 H 2 SO 4 Br NaOH Br 2 , h ν t-BuOK t-BuOH Cl 2 SO 3 H 2 SO 4 NO 2 H 2 CrO 4 FeBr 3 FeCl 3 HBr H 2 O 2
Practice HW Shabbir 320N Do Not Turn In 4 Q4 -List the product of the following sequence of reactions. Draw only the MAJOR product or products and indicate stereochemistry. When a racemic mixture is formed, mark the chiral center with an asterisk (*) and write “racemic” in the box. Br H O OH HO 1. 2. Mgº, diethyl ether H 3 O + , H 2 O 3. 4. H 3 O + , H 2 O O H H Cl O AlCl 3 O NaOH H 3 O + , H 2 O NH, Cat H 3 O + Cl O H 3 O + , H 2 O 1. 2. 3. 4. 5. 6. 1. HNO 3 H 2 SO 4 2. H 2 , Ni 3.NaNO 2 , HCl 4. KCN, CuCN 5. LiAlH 4 6. H 3 O + 7. Cl O
Practice HW Shabbir 320N Do Not Turn In 5 Q5 - (A-H) These are Synthesis question. Show how the starting material can be converted to the product through any of the reactions you have learnt in OChem.-I and OChem-II. Show all the reagents you need and indicate the stereochemistry when appropriate. You do not need to show arrow pushing like in a mechanism question, only the reactions. If a racemic mixture is formed mark the chiral center with an asterisk (*) and write “racemic” next to the two structures. All carbon atoms should come from the same starting material. Use as many molecules of the starting material as you might need to get to the product. Note is a reaction gives both ortho and para products you are allowed to isolate only one and move forward with your synthesis A) CH 3 OH OH CH 3 ?
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