Exam_3-Chem35-2007-answers

Exam_3-Chem35-2007-answers - Chemistry 35 Exam 3 Answers...

Info iconThis preview shows pages 1–4. Sign up to view the full content.

View Full Document Right Arrow Icon
1 Chemistry 35 Exam 3 Answers – May 2, 2007 Problem 1 . (24 points) Synthesis: Propose a series of reactions (reagents and conditions) that convert the Starting Material into the Product. You do NOT need to draw mechanisms for each reaction. Structure your answer as follows: Starting Material Reagents-1 Product 1 Reagents-2 Product 2 etc. as necessary A) (6 points) OH OH OH MsCl/pyridine SOCl 2 , PBr 3 , HBr/H 2 SO 4 HI, HCl/ZnCl 2 all OK OH OH OH TsCl, pyridine OTs hindered base t -BuOK, DBU LDA, Et 3 COK OsO 4 , ( t -BuOOH or NMO) OH H 2 SO 4 , 1 pt 2 pt OR 3 pt 3 pt OH any base 0 pts for OsO 4 alone is OK
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
2 B) (6 points) 1) BHR 2 (9-BBN, catecholborane, etc) 2) H 2 O 2 , NaOH OH MsCl/pyridine SOCl 2 , PBr 3 OK TsCl, pyridine OTs hindered base t -BuOK, DBU LDA, Et 3 COK 2 pt 2 pt 2 pt C) (6 points) Ph Ph Ph Ph 2 pt 2 pt Ph Ph Ph Ph Br 2 Ph Ph Br Br LDA OR t -BuOK, Ph Ph Lindlar, H 2 Lindlar is: Pd, BaSO 4 , quinoline OR Pd, CaCO 3 , quinoline, Pb(OAc) 2 2 pt (S,R) or (R,S) D) (6 points) OH H O 1 pt 3 pt OH H O 1) BHR 2 (9-BBN, catecholborane, etc) 2) H 2 O 2 , NaOH MsCl/pyridine OK SOCl 2 , PBr 3 OK if shown with inversion TsCl, pyridine hindered base t -BuOK, DBU LDA, Et 3 COK OTs OH Collins (CrO 3 /pyridine) or PCC or Swern 1 pt 1 pt
Background image of page 2
3 Problem 2 . (18 points) A) (6 points) Draw out all of the isomers, including stereoisomers, that have the formula C 4 H 8 . Include only structures with complete octets and zero formal charges. There may be more or fewer boxes than isomers. 1 pt each B) (12 points) Compounds A-D are four of the possible isomers or stereoisomers that have the formula C 4 H 8 . Compounds E-H are the major products from the reactions shown below. A H 2 SO 4 , H 2 O No Reaction B F is a meso compound CHCl 3 , NaOH C compound G has the molecular formula C 4 H 8 O G D E PCC F 1) BH 3 2) H 2 O 2 , NaOH 3) PCC Br 2 H is a meso compound H
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Image of page 4
This is the end of the preview. Sign up to access the rest of the document.

Page1 / 9

Exam_3-Chem35-2007-answers - Chemistry 35 Exam 3 Answers...

This preview shows document pages 1 - 4. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online