Chem335.SampleExam2.AnswerKey.pdf

Chem335.SampleExam2.AnswerKey.pdf - San Francisco State...

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Unformatted text preview: San Francisco State University ' Department of Chemistry and Biochemistry Organic Chemistry II: Sample Examination #2 March 18, 2015 -This examination contains 8 questions. Please confirm that you have all 10 pages. -Please put your name on this page and take a look at all the questions before starting. -Record your answers clearly in pencil in the space provided on this examination. ~There is scratch paper, a 1H NMR table and a periodic table attached. 1. 13 points 2. 16 points 3. 8 points 4. 4 points 5. 5 points 6. 10 points 7. 30 points 8. 14 points Total = 100 Name: AMW B} 1/10 1. (13 points) Please provide or circle the correct answer for each questions below. Only one answer will be accepted. Lo B) Please draw the structure of 3-fluoro-2,2-dimethylcyclohexanone. A) Please draw the structure of meta-ethylpentylbenzene. Tl C) Which of the following is a characteristic of the structure of a benzene ring? i) All carbon-carbon bonds are less than 1.0 A _ All carbons are sp3 hybridized (W All carbon-hydrogen bonds are 120° to the neighboring carbon-carbon bonds Iv) The aromatic ring has less than 10 kcallmol of resonance stabilization D) Which of the following is a characteristic of the cation intermediate that is formed during an electrophilic aromatic substitution reaction? i The intermediate is aromatic The intermediate contains an spa hybridized carbon iii) The cation is not resonance stabilized iv) The intermediate is long lasting E) Which of the following is not a contributing resonance structure for the electrophilic aromatic substitution of methoxybenzene with an electrophile (E)? F) Which of the following is a characteristic of the structure of a carbonyl group? ® The oxygen is sp2 hybridized ii) The oxygen is slightly acidic iii) The functional group is not polarized iv) The carbon is a nucleophilic site G) Which of the following would have the slowest rate of hydration? o o o ‘ NO\\ )LH \JLH \rlLH @H/ 2. (16 points) Please provide mechanisms for the following transformations. I_\ {m i o O o e (j H30 A “F l 1) PPhJQELL’} is) its ‘0 a; 3;." s3 “)2 52 O “a F ii F3“ (‘9: @112. m 2:“ “fifa V. s, -===~/ (3:) 1g / H A; g A --3 e._/' u ’ ’\ ’ 3 “is m) n {.f‘If‘AFQfi N) 9% I “’1: fish Q) Ck \ ”iiflflzi ’4 \ _ ~ / ".5 -_ (”\‘HWV‘ ; (“x ”*i i ‘ii i, \ es -'~ 3 \f/ K/ ‘\/ \\._./' V 3/10 3. (8 points) Please identify these compounds as: aromatic, non-aromatic, or anti- aromatic. In each of the cases the molecules should be considered planar in conformation. B) Milt. [3 El ‘ c) Mam D) M A B c D 4. (4 points) Rank the following in order of increasing rate of electrophilic aromatic substitution. Fill your answers in the box. CH3 cr=3 NH2 No2 A B c o 5. (5 points) The 1H-NMR spectrum (below) was acquired for an aromatic compound. In the box provided, please fill in the letter that corresponds to the structure most consistent with the spectrum. 4/10 6. (10 points) Draw only the major product for each of the following bromination reactions. Note: only one answer will be accepted and no points will be awarded if multiple answers are given. A) OMe 05M. Bra ——>— c) g FBBI'S Ear B) . L Q 02N FeBr3 (’9le 84" 0) Bra 8/ —)> O , FeBr3 D) Cl B ' \xC-l i 0’ 42—» iv a; n FeBra H z E. 1’ E) OMe if“ Br2 ’JNTNZ'VI? Hi —>- T <2) '4, FeBr ~ " H038 3 Hagg /k T 5/10 7. (30 pts) Provide the information that has been omitted in the following sequence. Cl‘fi: OMe i 1) BrzFeBra 0M6 Mg“ J o —2-- —:-- Br ' 2) H20, H2304 BI' / NEt o 005 - 1)Flh/H2 H‘a ' ,o 793%. - Parazl Et . <— ., NHEt NHEt 3) NaO‘Bu Et 1) HBCy2 Et » 2) NaOH, H202 Et . 2) H30 ', ’th HO Mn02 ¢ l Molecular Formula V 1) H2N~NH2 of Final Product = (.— C19H31N F a. 'n l/\,fi’h 2) NaOH, H20 8. (14 pts) Suggest a multi-step sequence that allows for- the conversion of the following starting materials to the corresponding products. (Note: you can use any additional starting materials that contain 3 carbons or less) A. NH © 3» @ L—r—I’mf” - .W m Cl Br L arias; W‘ CLZ. ’ QV‘QAPS ng U «3 “W’s? 0ng it“ “’ETML M \w WSW W’s 9(/ B. OH OH O 1" CE <~——“~3——-—— {Sew aomhgwislaw Br 5 9f _ . 5:3; 3:2; 1“ H2504 VLS Mllj K’Gwfli \/ . {13S} bin ck‘itj SQ3¥§ Firm“ “‘37 f lo 6 «M W I EH “0;; Ci“ Page; '- 75 ciKB f' 7/10 ...
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