Chem 360 Exam 2 Fall 2013 NAMEKa-:;S'{ot-\Ps+--~Prof. Bartmess (Carey8) )- This is a 55 min exam. Please think your answers1. (13) through before committing them to paper.- Be legible; if! can't read it, it's wrong.2. (12) - Don't put any answers on the back of the pages(although you can use the backs for scratch paper);3. (40) material on the back of pages will not be graded.- BE SURE THAT YOU HAVE FOUR DIFFERENT PAGES4. (12)5.(23)1.(13) Give the correct IUPAC nomenclature fo~the llowing structures. You can ignore RlSstereochemistry, but E,Z i fieeded..r-,,""\HO ~L7J02.(12) For each of the following h rizontal groups of3 acids, indicate which is the strongest acidon each line by writing "strongest' under it, and which is the weakest by writing "weakest"under it.OHCD0 EtC' "w-;:--r~ -~~~tt-Dct~~~e--t~'r~Cf:f-.,0c....-tOUlA- -4--D~ '\.~~ k-\[)('~\..\-~otBuC02H.~I..V+3<~~o2.(40) Fill in the missing reagent/reactant/product(s). Show all organic products. Pay attention toregiochemistry and stereochemistry. One arrow may mean more than one set or-reagents.a.o~OEtEtO-EtOHb.o~CIEtOHpyridinec.ooOHd.e.PhCH=OfBr.v..oo·~~ '-tdt:;:u+r0-0PhH4.(12) Present a high-yield synthesis ofQ1!.£of the following molecules, starting from whateverof the following are needed: non-cyclic mono-functional alcohols of four or fewer carbons, andany necessary reagents. All carbons in the target must come from the alcohols, but carbons in thereagents are "free". You need not give the mechanism for each step, but all necessary reagentsand solvents must be shown, and each chemical step (different reagents) must be clearlyindicated as a separate step. .Cb~~~~OEtbJ\Ldj'OEtOH~~ev-@t""3Jetz6 ~,/"-/~~"'@r@If'rf'-.*-t?l?1/'~~6H5. (23) a. Give a complete curved-arrow mechanism for formation of this dione from thereactants shown Show all intermediate structures and any important resonance forms of them.~ ~ ~OMeO-H30+0 0.~ .r<:+ ••Jl Jl+ MeOHPhOMe Ph/~~'-'1~MeOHC)yv~O ~O~r~ ~."'~ ~ [~. :;". ~Ql-\ ,'- ~ .§ct-t:cl~3 "' ~~(r~~~ ():::ED\ ~~<.tYlfthe H30+,is omitted, what product is obtained?~ c. If2-but.anone is used in place of acetone in part a., what would be obtained?V~. .. _
View Full Document
Unlocking...