CHEM 2312 Midterm: CHEM 2312 GT Examp2iia

Target Product 1 step(s) may generate multiple stereoisomer OH Possible Starting Materials H C Br Hac Br H3C NH HO HO OH Available Reagents OH OH OES OH OSS OH 1. Mix Reactants inDMSO (hot, dilute) (catalyst) 1. LIAIH42. H20, (H+) 1. DIBALH, -78 C2. H20, NaBH4CH30H CI, heat H2N NH2 HO MgTHF Zn heat CH 1. PPh 32. BuLi H3C Si CH3 2 Lihexane Et3N NH4+ F-

OH Cl 1 r) Answer: Br Answers: 1. Mg ether; 2. CO; 3. H,0: 4. S0Cla: 5. (CH)aCOH, pyridine. O 1. excess LAH 2. H,O (aq. workup) OH OH Answer:

Extra Credit Quiz (10 points) Student name: Date: Organic Chemistry 1, CHEM2423 What is the relationship in each of the following molecules? Do the drawings represent constitutional isomers or stereoisomers, or are they just different ways of drawing the same compound? If they are stereoisomers, are they enantiomers or diastereomers? Explain your answer by converting the drawings into the same represebataion, i.e. if you are comaring a Newman projection to a Fischer projection, you need convert both into either a Newman or Fischer projection. Assign all the absolute configurations as R or S to support your answer CH3 Br and Br-H Br CO-H CH CH3 CO,H -Br and ーCH3 CH,CH2 Br and CH,CH2 2OH CH OH (b) H and HO-H CH3 CH3 CH2OH CH2OH I and (CH),C (h) (CH)C OH OH H3C OH CHa CH3 CH