"Have a great summer!"

Transcription

1 Seat o. Section LAST AME FIRST AME (PLEASE PRIT CLEARLY!!) CEMISTRY 332B Section B (Dr. Arthur Winter) FIAL EXAM Tuesday, May 3, 2011 There are 12 pages to this exam (including this cover page). Check to make sure you have a complete exam. During tests and quizzes, all electronic devices (e.g., calculators and cell phones) and papers other than your test sheets must be turned off and completely out of sight. All book bags, books, etc., as well as jackets, coats and hats, etc., are to be on the floor UDER your seat. Please refrain from conversation until you leave and are outside the door. Thank you. "ave a great summer!"

2 ame (Please CLEARLY PRIT your name and CIRCLE your last name) CEMISTRY 332 FIAL EXAM Dr. Art Winter Tuesday, May 3, 2011 I. (20 points) II. (18 points) III. (42 points) IV. (40 points) V. (30 points) Extra Credit. (5 points) TTAL (150 points) 1

3 1. Give unambiguous names or structures to each of the following molecules (20 points): C!"D-glucofuranose Br pyridine cyclooctyl 2-methylpentanoate Draw Leu-Val-Phe (See extra credit page for amino acid structures) pentanoic anhydride trans-3,4-dihydroxycyclohexanone 2

4 2. Complete the following questions: a. Circle the molecule in each pair that is more acidic: (4 pts) F b. Circle the molecule in each pair that is more basic: (2 pts) 2 2 c. Write 1 o structure, 2 o structure, or 3 o structure next to the appropriate descriptor (3 pts) ow segments of the protein chain orient into patterns (e.g. α helix, β sheets) The amino acid sequence of a protein ow the entire protein folds over three- dimensional space d. Circle the 4 correct descriptors (one in each parenthesis) in the following statement that matches the following sugar: (4 points) This (reducing; non- reducing) sugar is a disaccharide of an (aldo; keto) hexose, which contains a (α; β)- (1,4 ; 1,6 ) linkage e. Circle the acid derivative functional group that would react if exactly one equivalent of a were added to the following molecule: (2 pts) Cl f.. Draw the structure of Glutamic Acid (Glu), that would predominate in neutral water. The pka of the sidechain carboxylic acid is (See extra credit problem for the structure of Glu). (3 pts) 3

5 3. Fill in the missing reagents, starting materials or products for 14 of 16 reactions below. Cross out the 2 problems you do not wish to have graded. o reaction is a possible answer. a. C b. 2 ab 4 (excess) 2. + workup c LiAl 4 (excess) 2. + workup d. + catalyst R Ph Ph n R e. Δ R n R + 2n Ph f. PCC (excess) Br 1. 2 S 2 g. Br 2. -, 2 4

6 2 Cl (2 equiv.) h. AlCl 3 i. C Ph j. k. SCl 2 int: this one has one more step than is immediately obvious l. Et Et m. 5

7 C 1. C, C , Pd 3. 2 n. C 2 2,! o. nylon n p. + 3 C 2 - Et 3 4. Complete 4 out of the following 5 mechanisms using the standard arrow- pushing conventions. Cross out the problem you do not wish to have graded. (40 points) a. Et Et- 6

8 2 + (cat) b. c. 2 C DCC + 7

9 + + 2 d. e. 2 Me 2 C Me 2 C Me - /Me Me 2 C! Me 2 C C 2 Me C 2 Me 8

10 5. Propose a multistep synthesis for three of the following four molecules, starting with the carbon sources indicated (for parts c and d) and/or any other carbon sources with no more than six carbons. You may use any additional reagents you need. You should indicate all intermediate compounds formed along the way, but no mechanisms are necessary. (30 points) a. b. 9

11 Ph c. Br d. 2 Ph Ph ignore stereoisomers 10

12 Extra Credit (5 points). "ow would you like to live in a looking- glass house, kitty? I wonder if they'd give you milk, there? Perhaps looking- glass milk isn't good to drink..." Lewis Carroll. In Alice in Wonderland, Alice is transported through the looking glass into a world that is the mirror image of the real world. Alice begins to feel hungry. She notices that there is bread, a bowl of wood chips, and 20 jars with each of the amino acid supplements, and a jug of water. Alice recalls that in the real world bread contains starch (α- linked D- glucose polymer), and that wood contains cellulose (β- linked D- glucose polymers). Is there anything in the room that Alice could eat and drink that would have nutritional value? Why or why not? Recalling - chem gives Alice a headache and she sees a bottle of Tylenol and a bottle of Advil. Which, if any, pills should she take to relieve her headache, and why? acetominophen (tylenol) ibuprofen (advil) 11