exam4key - First Three Letters of Last Name TA Name Exam 4...

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Unformatted text preview: First Three Letters of Last Name TA Name Exam 4 5.12 Spring 2005 Name Signature lD# Prerequisite (circle one): 5.112 5.111 3.091 1. Make sure your exam has 11 numbered pages plus a periodic table. 2. Write your initials on each page. 3. Look over entire exam before starting and carefully read all instructions. 4. Show work for partial credit. Possible Points Total 1. (10 points) a. Which compound is more susceptible to electrophilic aromatic substitution? 5— z wl'l'kcj’c‘w‘“ (903)“ + NH2 NHS Chaise) So &QacL\Jag (D E: b. Which carbonyl compound is more susceptible to nucleophilic attack? alét Lyle) Mare madam —— c. What is the purpose of the FeBr3 catalyst in an electrophilic aromatic substitution halogenation? It serves as a radical initiator It destabilizes the carbocation intermediate. e. Rank in order of acidity (1: most acidic). OH OH Initials Points 2. (12 points) Draw the structure of the MAJOR product of the following reactions. If there is no reaction, write “NR”. a. HNO3/HZSO4 b. c. d. O W Cg LiAIH4 90 ° U Initials Points 3. (15 points) Draw the structure of the MAJOR product of the following reactions. If there is no reaction, write “NR”. O PCC N {L Initials Points 4. (12 points) Provide the necessay reagents for the following transformations. More than one step may be required. (D MAL Col C 1J3 Initials Points 5. (4 points) The equilibrium constant for hydration of acetone is 2 x 103' which translates into a small percent conversion to the following hydrate. i __ HOXOH Kw: 2x 10-3: H30 CH3 H30 CH3 Would you expect the equilibrium constant for hexafluoroacetone to be smaller or larger than that for acetone? 0 HO OH 12?? X F30ACF3 F30 or:3 mfihyd \ -3 MW Keq greater than 2 x 10 Keq less than 2 x 10'3 6. (5 points) Draw a mechanism for the following transformation. d + £01 Cg) Jr (Di—\M“ (C) *5 / (A )\ A é\ I") i be “131* (3° N ,../ \N < f’ 9—,— ‘ 2 ‘ «A \J u \ 3 (\l 4:» gig} I Mao 0:33—06 ( /\ Initials [0 Points 7. A. (10 points) Draw a detailed mechanism for the reaction below. B. (2 points) In your mechanism clearly indicate the rate determining step of the reaction. Initials Points 8. (10 points) Draw a synthesis of the following product from the given starting materials (additional reagents will be necessary). Each step in your synthesis must be clearly shown, but no mechanism is required. 0 0W 6 Mr starting materials product éflzsv‘qr; (an LLowLJ € \w‘wuimkwx 3m)f: 8‘10 Point‘s (Fg ‘.’ l— wos ovw Contact) Bu’l' HAL "best \ Lmst‘ (2350 se leQLwQ) sjwlrlxes 35 73 a w.’[<}\5_ F thLi ?(;L\ Initials Points 9. (10 points) Draw a synthesis of the following product from the given starting materials (additional reagents will be necessary). Each step in your synthesis must be clearly shown, but no mechanism is required. HO Product Initials Points 10. (10 points) Draw a synthesis of the following product from the given starting materials (additional reagents will be necessary). Each step in your synthesis must be clearly shown, but no mechanism is required. HO HO/\/OH ' OH /\/OH 0 product starting materials (3 H + Cl ” 9 Y Li [Jo /\/‘G u o L I [JQLC’rLO-I V I u \—/\/61~‘ - M307 0 a MAOL. Initials Points Extra Credit:(2 points) Furan is readily acetylated with acetic anhydride and a Lewis acid such as BF3. Predict the major regioisomer produced in this reaction and justify your reasoning with resonance structures. [3) ioi ii» fix? 0 J“ 4 O '3 U C) / \_ , <\ #3 as <21 C a (1—)? 3 ‘9’ “ML ~L /O\ /O\\ 4- H . \\——-l I 9x {£3‘NVL\'\. l; /©\_..l:' O i Initials ‘ Points 10 ...
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This note was uploaded on 01/30/2011 for the course CHEM 2OA3 taught by Professor Stover during the Spring '10 term at McMaster University.

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exam4key - First Three Letters of Last Name TA Name Exam 4...

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