04 Substitution Reactions Worksheet

04 Substitution Reactions Worksheet - - Br-C C H 3 C CH 3...

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CHEMISTRY 225 SUBSTITUTION REACTIONS WORKSHEET Tert -butyl ethyl ether (TBEE) is an oxygenated gasoline additive. It can be synthesized in the lab by the reaction of tert -butyl bromide and ethanol. Write a detailed, stepwise reaction mechanism to account for the synthesis of TBEE. A complete reaction mechanism will include structures of all intermediates and curved arrows to represent the "flow" of an electron pair. It is not necessary to draw structures for transition states. C Br CH 3 H 3 C CH 3 CH 3 CH 2 OH C CH 3 H 3 C CH 3 OCH 2 CH 3 (+ HBr) TBEE The cover of a recent issue of the Journal of Organic Chemistry (Volume 66, Number 9, May 4, 2001) contained the caption "100 years of Carbocations". Included on the cover were the two carbocations shown below. The triphenylmethyl cation is known to be more stable than the tert - butyl cation. Use this information to comment on the relative reactivity of triphenylmethyl bromide and tert -butyl bromide under conditions favoring S N 1-type dissociation (reactions below). C Br
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Unformatted text preview: - Br-C C H 3 C CH 3 CH 3 Br- Br-C H 3 C CH 3 CH 3 Consider the S N 2 reaction below. N CH 3 + CH 3 Br N CH 3 CH 3 Br ● (3) Identify by structure: the nucleophile _________________________ the electrophile _________________________ the leaving group ________________________ ● (2) What would be the impact on the rate of this reaction if the concentrations of the two reactants were doubled? Explain briefly. ● (3) Suggest an alternate route to the product by an intramolecular substitution reaction. HINT: The bond to be formed in this reaction has been located for you. N CH 3 CH 3 Br BONUS QUESTION! Among the chemical agents used to hasten the recent demise of Oklahoma City bomber Timothy McVeigh was the steroidal muscle relaxant pancuronium bromide. Pancuronium bromide can be prepared by the reaction below. Deduce the structure of pancuronium bromide. CH3 H3C OCOCH3 CH3CO2 N N excess CH 3 Br pancuronium bromide...
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This note was uploaded on 06/18/2010 for the course CHEM 225 taught by Professor Markdec during the Spring '10 term at University of Michigan-Dearborn.

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04 Substitution Reactions Worksheet - - Br-C C H 3 C CH 3...

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