04 Substitution Reactions Worksheet Key

04 Substitution Reactions Worksheet Key - CHEMISTRY 225 i4...

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Unformatted text preview: CHEMISTRY 225 i4; 7 SUBSTITUTION REACTIONS WORKSHEET Tart-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 wili include structures of all intermediates and curved arrows to represent the "flow" of an eiectron pair. It is not necessary to draw structures for transition states. CH ' CH I 690 i | 3 H3C—----C-----Br H3C—C—OCH20H3 (+ HBr} CHgCHgOH l | CH3 CH3 " TBEE / h H + 9 Cr“; «4 ... as I . “’7 6.3 ~—-—-—--—) alga“ ale?) uh, .. C (:1); l on}, M; H 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". Inciuded on the cover were the two carbocations shown below. The triphenylmethyl cation is known to be more stable than the terr- butyl cation. Use this information to cornment on the relative reactivity of triphenylmethyl bromide and Icrt-butyl bromide under conditions favoring SN l-type disseciation (reactions below). I _- _ CH3 CH - Br 332;. i - Br 3 | 0 Br -—-—-—» 1-,:- c a; H30 -—c — Br —» H30 -- - or?) I I I :7- I m Wei vtc~aJxxt wwrcuutii- i“- 714; 4”! via an Lo, amt; fled-e {Orv—— Mcp‘i' 9i‘c-LLL MrLDUaJIDuL Limte flat. ‘icquwm7iw—eri-L7i cell's“. his» wo~r giftifli-L mm 7L1 ‘i?_-+-— Lmi7i can l‘fiu) hi FHC‘LAJI; inan Li’tiylw‘fl Lymwmir. musi Le MDVC fo‘J-t Linc iv; ' (wit, (.4 a. {mi- mk) n” in}- L471 amt Consider the 8x2 reaction below. {I \H e < JN—CH3 + CH3Br ~——n- r'\ [email protected] B; E \\\—~—J \m—r CH3 0 (3) Identify by structure: F} _ a 4 the nucleophile \——- ?- “ the electrophile lg "_ . I; Q the leavmg group _~f__ I (2) What would be the impact on the rate of this reaction if the concentrations of the two reactants were doubled? Explain briefly. _ TL”— Vflit wcuidi imtveagL L7 4 {Leif}- fl {@Hv. 90 W V a La la Us 1&3!»- Hl‘lv- on»; 9N2 verbatim“ tab/L [Mikkel-Ll- o (3) Suggest an alternate route to the product by an tntramolecm’ar substitution reaction. HINT: The bond to be formed in this reaction has been located for you. i :7" \i a rd ,CH3 9 . we ~—~ cuz out one. (Him-JP 6 (+3 Br I \ "a \ W3, CH3 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 paricuronium bromide. i_._. CH3 ococm i \l H30 excess ‘ N ,K " CH Br xv -’ “1/- v/ I 3 I I. | I ‘|I-" CH3COz' cage»: ' pancuroriiiiin bro-militia ...
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04 Substitution Reactions Worksheet Key - CHEMISTRY 225 i4...

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