Chemistry 30A Spring 2004 Final Exam Part A Page 1 1 15 points Write the organic product s in the boxes If more than one organic product is formed indicate which product is major Be sure to indicate stereochemistry if relevant If no reaction occurs write NR Do not include any mechanism details 1 O3 a Ph Ph 2 CH3 2S H2 Pt b Ph Ph OsO4 c Ph Ph H2O2 1 BH3 d 2 HO H2O2 Ph e Br2 large excess CH3 h 2 Consider this reaction H2SO4 a 6 points Provide a mechanism for this reaction b 3 points Finish this statement in 20 words or less This reaction does not occur in pure water no H2SO4 because Chemistry 30A Spring 2004 Final Exam Part A Br Br2 H2O 3 Consider this reaction OH OH or Ph Ph Page 2 Br Ph a 1 point Circle the major product b 6 points Provide a mechanism for the formation of the major product c 6 points Briefly explain 2 3 sentences you choice of major product d 1 point The cation involved in this reaction mechanism that includes bromine in a ring is called a n O aqueous H2SO4 4 Consider this reaction PhC or CH Ph CHO Ph a 1 point Circle the major product b 10 points Provide a mechanism for the formation of the major product c 3 points Finish this statement in 20 words or less This is the major product because Chemistry 30A Spring 2004 Final Exam Part A Page 3 5 15 points Write a reaction to clearly illustrate each concept The reactions must include all reactants and products but do not include any mechanism details a Syn addition b Anti Markovnikov addition to form an alcohol c Oxidation of an alkene d Oxymercuration to form a tertiary alcohol e Reduction of an alkyne to give a cis alkene 6 2 points Finish this sentence in ten words or less BH3 is electrophilic because 7 6 points Circle the appropriate response a Hybridization of carbon in a methyl radical sp3 b Most stable radical c Most stable radical CH3 CH2CH2CH3 CH3CHCH3 sp2 sp Not hybridized CH3 3C CH3 2N N CH3 2 Chemistry 30A Spring 2004 Final Exam Part A Page 4 8 5 points Like carbocations radicals have a limited number of mechanism fates Finish the radical fate illustrations given below with the appropriate curved arrows and mechanism step products If the fate may be completed in more than one way select the most likely pathway Each answer should not extend beyond a single mechanism step Br Atom transfer Br Addition to a pi bond The name of the third common radical fate not given above is 9 6 points List one significant difference and two significant similarities between carbocations and radicals Avoid trivialities such as both can have carbon Less significant answers may receive less credit Difference Similarity Similarity 10 4 points Finish each statement in ten words or less a The radical phenomenon that allows a small amount of a chlorofluorocarbon to convert many moles of ozone into dioxygen O2 is b In cells antioxidants protect against damage from a molecule called Chemistry 30A Spring 2004 Final Exam Part A Page 5 11 Consider this reaction HBr HOOH or Br Br a 1 point Circle the major product b 9 points Write the best mechanism for the formation of the major product