Chem335.SampleExam3.AnswerKey.pdf

Chem335.SampleExam3.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 #3 April 22, 2015 oThis examination contains 6 questions. Please confirm that you have all 11 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. 16 points 2. 20 points 3. ' 15 points 4. 15 points 5. 24 points 6. 10 points Total = 100 Name: WSW” '1”! 1/11 1. (16 points) Please provide or circle the correct answer for each questions below. Only one answer will be accepted. A) For both of the molecules shown, circle the most acidic bolded hydrogen. (9" ° 0 B) C) D) Rank the following in order of increasing rate of nucleophilic acyl substitution. Fill your answers in the box. least ' Me 0 Me active B E) Which of the following statements concerning the reactions of a,[3-unsaturated ketones with nucleophiles is true? i) Amines prefer to add at the carbonyl carbon LiAlH4 prefers to react with the fi-postion w, Enolates prefer to add at the B—postion ' Cuprates prefer to add at the carbonyl carbon 2/11 F) 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. A represents the aromatic signals (already given). 3/11 2. (20 points) Please provide mechanisms for the following sequence. 5m srz 0H 01k 0 0 NaOEt NaBH__)L )LOH /ILH JV EtOH 6* EtOH @TG 6 $5 f GL1 Sky 23‘ 3 : @ f: a G5 :4 H ya GM 0 a = (66 .-——> Q a”; ,. 1" fl “ «5” /""“‘ 8H c /\?/{:’i <9" / \uggf‘g /\°"( ‘ H 4/11 3A. (9 points) Draw only the major product for each of the reactions. Note: one answer will be accepted and no points will be {Dewarded if multiple answers are given. i) HJkAph NaOH, AH20 H‘J’ [iw @ Q iii) 0 O NaOH, AH20 €97) prl’JL\¢5’1\\ 4- pr,’ll\~ Eflfnli B. (6 points) Draw the starting materials that would lead to the shown product by the indicated transformation. AIdoI it) Reaction Via: H '9 CD Robinson H Annulation (”‘1 \/ 5/11 4. (15 points) Draw only the major product for each of the following reactions. Note: only one answer will be accepted and no points will be awarded if multiple answers are given. all A) 0 1) LiA|H4 J Ph ’ILOMe 2) H309 fa" «D B) o 1) DIBAL )L Ph JLNMe2 2) H300 7117;!" H C) o 1) LiAlH4 __).. 1m Ph JLNMea 2) H30° Pl" /\ N 2’ G D 1 M -M B H ) Ph/c” ———)-’ e 99 ' PM /\Me., 2)H30 E) j /N 1)D|BAL “P1 / —-* Ph/ 2)[email protected] F" 6/11 5. (24 points) Provide the information that has been omitted in the sequences. 7/11 6. (10 points) Suggest a multi—step sequence that allows for the conversion of the following starting materials to the corresponding products. (Note: any additional starting materials can be used that contain 2 carbons or less) ', View.) C‘C Email ©AB' 1’5 mm" '00» NW MM 0 9M ms; diam 0 Mel own/rim cw 8/11 ...
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  • Summer '13
  • Dr.JenniferTripp
  • Chemistry, Organic chemistry, Amine, San Francisco State University, Department of Chemistry and Biochemistry, San Francisco State

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