308_exam_3_fall2014 - Name Chem 308 Exam 3 Spring 2014...

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Unformatted text preview: Name Chem 308, Exam 3 Spring 2014 1X. (12 points) Using propanal, any reagent having one carbon as your source of carbon and any other necessary reagents, devise a synthetic sequence for the formation of N-propylbutanamide. Show distinct chemical reactions for each step in the sequence. Indicate any specifically required solvents and reagents for all steps in the sequence. Put reagents and solvents above the arrow and any work up below the arrow. Once you write the structure of a compound you can designate it with a Roman numeral and use that in the rest of the sequence. Remember, count the carbons! \JLH a O Nw‘ts + \/u\ u 4 \/\OH not} /" {5361. \/\0H d wolf-‘6 (5)0er Name Chem 308, Exam 3 Spring 2014 67A”; fl: 3“ 2Y. (12 points) Write out the complete mechanism of the reactions shown below. Be sure to show ali charges, lone pairs that are involved in the reaction and to show movement of electrons with appropriate curved arrows. 0 o A 01-! . _._).. + —OH O 0/ H20 .1 De (1“ “33: H J +30%! 0/ Z \/ o __,,/~~ ? ‘1': Ci? .5..- Z We”? V‘QH’ I? “' mu Q _ O M H i. H -(-'—'\'\f ‘3 K II #0 V\OC1Rr-\_:/"Q Q C?" B. Describe briefly (ten words or less) two major differences between the hydrolysis of esters with aqueous base and with aqueous acid. 1 75744.11!» Jo‘s 531:". an... “up Mafia—2' Name Chem 308, Exam 3 Spring 2014 2* o o C... #Qfll'! .L:& a :0" R ti "Ev-2) \s/ltxgu +' HCL. \/ Cl. ran, SAHZ RS 35’. 3X. tile—points) Write the structure of a compound having a molecular formula of C7H1203 and the proton and 130 spectra shown. 3 H sing. 1 mafia—1 260 1—1 o '1éo T140 '1éo ?a INTS F5“- 3 pl QAJ'Lfia‘JVL' HtZTH YL 2- HEMYL ’3-oxo I72 UTnquTQ' 2 Pawns IUPAC name Name Chem 308, Exam 3 Spring 2014 4X. (12 points) A. Explain briefly (ten words or less), using examples of specific compounds, the two major factors affecting the reactivity of acyl compounds in nucleophilic substitution. fLE'CTZflPHIL-IUTV’ or amazon“ 6,412.60.» . ————_———_——__——r 1 Q 3 ,JLCL No.16; ELEorer/uc. Trifle) 2L5)“; C) New C) ' + GPTlOf-JHL /‘_-I‘____C|_ 9...}; flkcg C IJLHHL {-25 /:Huz '3 2. @fld‘nfixvv or: LEAVING: cakaup 2 Fr? /"*~c._, flex—H LIBJ 3A5r¢ anagram: _..--"' p.42 55;.Sor:e;:i B. Write the mechanisms for the following reactions. O HO OH ..0 9 )K + -OH "' X a? n ‘0“ ' .2 -i R + C)! '—--b 3 /A\:/" w- '33:! :t\ ,! 'ParHT ’3": H" «r an ’flIBSfN‘ Agape-=3 O O A + ————," 3' OH Name Chem 308, Exam 3 Spring 2014 5X. (12 points) Fill in the missing reactants, products or reagents for the following reactions. 0 O NaOH 09 u _ Z A NH! _———+ H 1;”, H20,heat Name Chem 308, Exam 3 Spring 2014 6X. (12 points) Using only benzene as your only source of carbon and any necessary reagents, devise a synthetic sequence for the formation of m- bromofluorobenzene. Show distinct chemical reactions for each step in the sequence. Indicate any specifically required solvents and reagents for all steps in the sequence. Put reagents and solvents above the arrow and any work up below the arrow. Once you write the structure of a compound you can designate it with a Roman numeral and use that in the rest of the sequence. | Br 881—75 H-S' 6V x5 HDOT: a r ,r ———e (7” 2 H2503: / F1 5123 + .. STE r402 27‘ a “H3 pong co U ,_2> I _r' z + 3 D I [ML m2 #2" Pt '2’ ,2 a: V5 22.“: "‘ A $001 ‘2); LED“; Name 5’4 r“; n 5 Chem 308, Exam 3 Spring 2014 ' 7 X W. (12 points) Fill in the missing reactants, products or reagents for the following reactions. 1) 0:31” an» 2: A ‘0) MILO) Aafl ‘5) A ...
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