EXAM 3 - Nfiv em ner 5 was IDIH Be sum 10...

Unformatted text preview: Nfiv em ner' 5, was IDIH Be sum 10 mafi-eaflh-qfleflifinéfififfi]l§fi This tagt'mtifi'tzfie-takéfi in-E'em Teststaken in germ-i1 will rim be graded. Pani‘al craditwill bar-assigned-where wopriate. Ta mve . fifllc'redit'yph musLamWéE-gach quésfi'on mplémly, Reta; and-gnarl luck“ 2. 1. {-112} ptsj-P-ruvidé the apprapriajte IUPAC 0r amnion mum: fur‘the'fuflawing . cumpnunds: '3. first U! CI-[ENIIETR-Y 2-2-12 Scam EMS E E Total: 2. (1d pts] in} Rank the acidity of the following phenols from feast {I} to most {.1} acidic. Write the corresponding number for each compound in the boxes provided below: H H 0H 6:“ E: NH .54:ch a {I}.- {b} Draw ali'of the ossible resonance structures [or the fltlfl‘ll atebase of the strongest acid. Justify your answer from above hy'circling the specific resonance structure-[5} that stabilize(o) the strongest acid’a conjugate'base to the greatest extent: 3. (3 pts) Provide the appropriate starting materials for each reaction type listed below that will generate the ether product shown below in the best overall field {ie. minimized product mixtures}: 04% Williamson Ether Synthesis: Aikoxvmerouration: \/l air a _ caéill‘iflfi 4. {4 pts} Rank the following-sets f compounds in order of their increasing reactivityr toward nncicophilic ' . Dr'der this set from least {1] to most [£1 reactive. 1Write the appropriate numbers in the spaces provided. 9 “H2 o' o mots 0- H CO . H393 Wimp. LI) 5. {1 2- pie} ”Provide a eomplete, detailed and stepwise meehanism for the following nucleophilie Substitution reaction. In order to r'eeeive'iull credit Eon must'show all electron movement and rovide all of the s ro rinte intermediates for this reaction: ”och. I Has“! fi. {'1 flpts} Previde a series of steps to accomplish the feltewing synthetic trans‘fermetien. Yen must preside all apprepriste reagents and intermedietes fer yeur synthesis. fl reattien mechaniSms arreiws are ne'ees'sarv In answer this uestitm. [Hint If yen are having difficulty, tr}r war-king backwards free: the preduet to the starting materials.] 0 HOW Mulfigfe Siege H Br Raquired '1. (1o puts] Complete the following reaction eohemes by providing the appropriate reagentsIs] or all possible produofls'}: 1. HMHOE, H20, NaOH 2 Hail” W Hint: Very Stew Reactidn 8'. [16 pts] Eemplete the [allowing reaction schemes by pruviding- the appropriate starting materialfi], reagentsifie} er maier preduetlfe}. Be sure to indicate proper stereeehemistry where necessary: A H 1. mew. EtOH fi/LJOH 1/ 2- H313” D u . . ._ D 1. acne-as- GHal'u! Br + H Y\D/]\/ _*#_g_+2 Hat)” HE) /\r 9. [14 pts) Complete the falldwing reaction schemes by providing the appropriate starting materiafls), reagentsfs] ur meinr pruducfls}. Be sure to indicate proper stereflehemistry where ne'eeseary: ' I E .- —-:-- 2.H20.NaOH /\ 5H ...
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