{[ promptMessage ]}

Bookmark it

{[ promptMessage ]}

MT2_Key - Second Examination Chemistry 128B(Closed book no...

Info icon This preview shows pages 1–4. Sign up to view the full content.

View Full Document Right Arrow Icon
Image of page 1

Info icon This preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 2
Image of page 3

Info icon This preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 4
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: Second Examination Chemistry 128B May 18, 2011 (Closed book, no models) 6) Name JKE L; (Please print) Last First Middle initial Last 4 digits of your student ID Number: l‘his exam consists of4 pages (including this page) and 6 questions. Do not turn the pages until 12:10 PM. i‘urn in your paper by 1 PM. Put your initials in the upper right corner ofthe next 3 pages. Be sure you have pages 2—4. Please answer clearly in the spaces provided. Back ot‘the pages are only for scratch work. Any request for regrading should be done according to the TA’s instruction. 8:")1i11g 201 l 1288 Midterm 2 Page 2 Initials l. 1 IS pts) Multiple choice. Circle the best answer. 1111 Best way to convert JVCHO into M l. CH3MgI 1. CHzlz 2. COHC st()4, 120°C 2. KOC(CH3)3 (h) ls methyl cyclohexanecarboxylate CH; 1) O Uko 0 C113 E I \ll/ CH3 0 c) CHACHO will give 1H NMR signals at about 2 and 8 ppm 4 and 8 ppm 2 and 10 ppm 4 and 10 ppm if i“ d The reaction ) /(‘,\ : ¢C\ is an example of H3(‘ H H2C 11 resonance deshielding conjugation OC(CH3)3 ”C(CHsh :0) Best way to convert into 0 Wolff-Kishner Reduction Clemmensen Reduction Jones Oxidation I . 1 l5 pts) Formulate a detailed, step-by-step mechanism and give the product for the following reaction. ;;(1 ~/‘ H+ O 0* \ (2* 1312, CH coon CHZBr t H2 ___> (3:112 | H S )ring 201 l 1288 Midterm 2 Page 3 lnitials_ 3. (24 pts) Draw the structure of the expected major product of each reaction shown below Write 'NR‘ =1 no reaction occurs. Pay attention to stereochemistry. 0 OH (_)H A 1. LiAlH4,2. 1130+ ? (1" ~ + vY\ : o catNaOD D20 1h) WE racemic H Zn(Hg), conc HCl A (C! O OH 1d) Er; HCN NaCN CN OH . . CO H Product of reaction 'd',above M d— 2 Q CHZOH O o D < cat H+ h 0— C112 OH 1 L‘ 4. (_ l4 pts) A molecule has the molecular formula CgHioo and the spectra below. Propose a structure. \\ l/ \‘, ,-"\ f \ i ’ 1‘ “('1 f ‘ filli/ ‘14 V! i it ll 5 hi l l 6H,d0ublet 1 ill 1‘ if} 1; 1 ‘ M 1 ‘ 1‘ i if ll 1 ‘ 3 l“ ' 1i 3500 3000 2500 2000 1500 1000 500 cm-1 l ’ ZHadoublet\ 1H 1 l o i ”a ,, , ,. .Ju l 17*] TM} 7""T 'fi' ifir *r'rr-"Twrw 1W1 ;' 1"1 1 H 6 12 10 8 6 4 2 0 ppm 8.11ng 201 l 1288 Midterm 2 Page 4 Initials__ 5. l l5 ots) (a) A molecule has the molecular formula (35H1002 with 1H NMR and IR spectra shown below. Assrgn a reasonable structure to this molecule. 9H,singlet. 3 ‘00 3000 2500 2000 1500 1000 7 500 -1 3 cm 1H, broad singlet / ‘— i i l i I ‘ l i 1 i '1 a 12 10 8 6 4 2 (h) Propose 21 synthesis of this molecule from any organic compound of 4 carbons or less. 1. (:02 Mg 2. Hr. H20 Br —————> MgBr ————> COZH (‘()2H 0 ppm 6. l :7 pts) Write a detailed, step—by-step mechanism and the final product for the reaction below. Hints: The final product has the composition C6H1202 and the 1H NMR shown below, right. :():A Ht w M CH CH OH tH+ 11+ H 3 2 , ca .r (C 4H802 ) OH :OH + :OH I" .. ___, H HUM 01f ——* o \_./ H i 3H,triplet K + A V ‘ o : o HQCHZLH3 2H.quartet \ 1111H 111 \ # /CH2CH3 Hug/(mm. o i 1 4H 1 iii. A .1. o o '5 r? 4 3 2 1 Oppm ...
View Full Document

{[ snackBarMessage ]}

What students are saying

  • Left Quote Icon

    As a current student on this bumpy collegiate pathway, I stumbled upon Course Hero, where I can find study resources for nearly all my courses, get online help from tutors 24/7, and even share my old projects, papers, and lecture notes with other students.

    Student Picture

    Kiran Temple University Fox School of Business ‘17, Course Hero Intern

  • Left Quote Icon

    I cannot even describe how much Course Hero helped me this summer. It’s truly become something I can always rely on and help me. In the end, I was not only able to survive summer classes, but I was able to thrive thanks to Course Hero.

    Student Picture

    Dana University of Pennsylvania ‘17, Course Hero Intern

  • Left Quote Icon

    The ability to access any university’s resources through Course Hero proved invaluable in my case. I was behind on Tulane coursework and actually used UCLA’s materials to help me move forward and get everything together on time.

    Student Picture

    Jill Tulane University ‘16, Course Hero Intern