Test 2 2536 08 solution

Test 2 2536 08 solution - 1 Chem 2536 Spring 2008 Test 2

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Unformatted text preview: 1 Chem 2536 Spring 2008 Test 2 Name_________________________________________ Pledge: I have neither given nor received information on this test.___________________________________________________ 1) Show the nucleophilic acylsubstitution mechanism, product, and byproduct for the reaction below. Show correct reaction arrows and acid/base steps when applicable. Use curved arrows to show the electron movement. Label the leaving group, nucleophile and electrophile. ( pts) 2) Rank the compounds from most electrophilic (1) to least electrophilic (3). _____ _____ _____ Page 1 2 3) Propose a mechanism to explain the formation of the following byproduct. Do not add any reagents, use those given. ( pts) 4) Rank the following from strongest (1) to weakest (4) base. ( pts) _______ _______ _______ _______ Page 2 3 5) Fill in the 1H NMR table for the following compound. Label the H's on the structure. Hydrogen (Label with a,b,c.....) Chem shift (ppm) Integration Shape (splitting) 6) Draw the following compounds. a. 2propylpentanoyl chloride b. ethylmethanoate Page 3 4 7) a. Give the structure of the isomer of C4H9Br shown in the 1H NMR below. b. Label the integration ratio for each signal in the boxes above each signal. c. Label the hydrogens on the NMR and structure. ( pts) 8) Give the major organic product(s) of the following reactions. O a. Page 4 HOCCH2CH2CH2CH3 + H2NCH3 5 b. c. d. e. Page 5 6 Table of some reagents: Zn(Hg)/HCl MnO2 KMnO4 NBS NaNO2/HCl/H2O/0 C SOCl2 9) Provide methods and reagents necessary to prepare the following products from the given starting material. Show products of intermediate reactions. (5 pts ea) Extra credit (3pts): Which category of fatty acids is proving most detrimental to our health? 1 H NMR chemical shifts (ppm) Page 6 7 Page 7 8 Top of Periodic Table 2 3 4 5 6 4 Be 12 Mg 20 Ca 38 Sr 21 Sc 39 Y 22 Ti 40 Zr 23 V 41 Nb 24 Cr 42 Mo 1 1 H 3 Li 11 Na 19 K 37 Rb 7 25 M 43 Tc 8 26 Fe 44 Ru 9 27 Co 45 Rh 10 28 Ni 46 Pd 11 29 Cu 47 Ag 12 30 Zn 48 Cd 13 5 B 13 Al 31 Ga 49 In 14 6 C 14 Si 32 Ge 50 Sn 15 7 N 15 P 33 As 51 Sb 16 8 O 16 S 34 Se 52 Te 17 9 F 17 Cl 35 Br 53 I 18 2 He 10 Ne 18 Ar 36 Kr 54 Xe Page 8 ...
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