Chem210-1-2007-FinalExamAnswers

Chem210-1-2007-FinalExamAnswers - Chem 210-1, Section 02,...

Info iconThis preview shows pages 1–8. Sign up to view the full content.

View Full Document Right Arrow Icon
Background image of page 1

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

View Full DocumentRight Arrow Icon
Background image of page 2
Background image of page 3

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

View Full DocumentRight Arrow Icon
Background image of page 4
Background image of page 5

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

View Full DocumentRight Arrow Icon
Background image of page 6
Background image of page 7

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

View Full DocumentRight Arrow Icon
Background image of page 8
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: Chem 210-1, Section 02, December 11, 2007, Final Exam NAME: A MSWEES This exam has 200 total points with the point breakdown for each problem given below. Please read the entire exam before you begin! It witi help you budget your time. 1. (25 points total) A. (10 points) Give the correct structure of (1S,28)—1-bromo-1,2~diphenylpropane. B) (10 points) Give the mechanism for its reaction with sodium methoxide and the product that forms. C) (5 points) Name the product correctly. 2. (25 points) Synthesize the following compound starting from any alkyl halide with 2 carbons or less and acetone. (Hint: you cannot start with acetylene). CH3 thew OH I) i CZC“N ’f" Clif3~ C "LECH E”; fl g a. J 2.) [’50 0M f W‘l/Wz #CECH T fiiflm aft “HOT” [QOH Br; .. CH (—H CHECHZB’I/ F? <1ng C”; 7 1 Z l1 Br BA, 3. (25 points) Propose mechanisms for the following transformations: A) (15 points) H30 H3 H3CK-CH3 EtOH H OEt m—uu—y + HBr heat (3" H3: or; H c :K m ”‘ 3 C“; E: y #- 81 HQ . 13C ch‘ 3 “3C “*3 + H3 6’63 Ag EtOI 14‘ 7 553‘ "J? H 5* f“ .. + "‘ £6014 Lit-M?— B) (10 points) H +0 -—----~ H cytochrome P450 1+ f+ 9 Fe (w) fa (m) 4. (25 points) Using the given starting materiai, any necessary inorganic reagents, and any carbon—containing compound having no more than 1 carbon atom, show how to synthesize the product. --© Br CH30 _—-——+ E“ CHO H0573 3 9—“ Q a) (Elf—7: T i) Bltg/THF a Hag/W" 57! it 5. (25 points total) When the following reaction is carried out under the conditions given, the reaction is strongly exothermic and proceeds rapidly: 0:0: K+'OtBu "H Br DMF A) (10 points) Give the product of this reaction and show the mechanism of its formation. pgf‘om l/ _._.__._._. a? 4— HEAL” GAR 7 $151 8) (10 points) Draw an energy vs. reaction coordinate diagram for the rate-limiting step of this reaction (assume that it is not proton transfer), and label the reactant, the product, the transition state, and the activation barrier. [718. x Ga. Ac” t1 7 he. C) (5 points) Using DMF (N,N—dimethylformamide) as the solvent greatly accelerates the rate of this reaction. Why? 0' "T W‘WW ‘ WHMHW 6. (25 points) The foEiowing chiraf epoxide can be prepared in a single step from the corresponding chiral alkene. V H ‘\H O ’H A) (5 points) Give the structure of a reagent that can perform this transformation in one step from the corresponding chiral alkene. M7». y @j- {€*§*0’o4+ to Ca Q/0“O“H HOH3C~OPO~1L€ b B) (5 points) Give the number of isomers formed in this epoxidation reaction. Are they separable? Why or why not? 2 WW dam“ M m— 51> M"W” fit 3 . raw the structures of the product (or products) of the following C) (10 points) reaction with full stereochemical details using a perspective drawing of the cyclohexane ring (not a flat picture like that shown below): 1’ tt ‘+ crab H M), H) (c WA /® 0% H a D) (5 points) Label each asymmetric carbon atom in each product given in part C) and assign their (R,S) configurations. M W $1. (25 points) (5 points each) Give the products of the following reactions: A) _ OH V11 ++ are - 5 am 0/ 2) H3O+ C 5 Z ‘ 3 cr+ 3 8) ({DH 1) CH3LE ___.. 0+ " c, -— (1+ 6+ 2) H30+ C H3 2 i Z 3 fig C) fl— 0 1)CH3Li '. ff ——-—-—-> = 6+ - “C \JLC’ 2) H30+ CH3 2. I 3 mg 6% D) i CHsoM 1) Nam-I4 * / 2) H30+ g o E) W I 0 1) LiAIH4 . —> I (fr CH ChL CHsom/QK 2) H30+ H 0 Cfle C 1% Z 3 8. (25 points) Using the given starting material, any necessary inorganic reagents, and any carbon-containing compound having no more than 6 carbon atoms, show how to synthesize the product. b> l /\ / lg,l N32 Etzo Hg’efi /\ ’- f > /\ ...
View Full Document

Page1 / 8

Chem210-1-2007-FinalExamAnswers - Chem 210-1, Section 02,...

This preview shows document pages 1 - 8. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online