351 C11 Smith key

351 C11 Smith key - o let's step it up a notch With...

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#^ Chemistry 351 Fall2008 Chapter l1 l. Rank the acidity of an alkane, an alkene. and an alkyne. rnof€ aci{rL H P-C:--a-t{ r{5 2. Predict the product of hydrohalogenation of 3-hexyne using IiBr. Why is the geminal dihalide formed and not the vicinal dihalide? Use the mechanism to iustifv vour answer. OT e/ 4. Synthesize the product fronr the given starting material. you may use any carbon reactant with 2 carbons or less, as well as any reagent. P--c+{zcrt3 5O 2w4"4 r)p#\3,T+\F I z)HloL, F\z-O, 0ll- F OH d Ts c\ :___--P glridina ./*'."' <t 4 Mil- ; Briefly give a chemical reason fbr the trend. 1} e t? *U+^\ is more elt<*rw,egoflve. ff.r'l h.rorte-s ft e Fl rnore ocil;c.J {h€ -$. bore v\ore
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5. Now that you are feeling a little more confident, bromide as your only sources of carbon, synthesize
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Unformatted text preview: o let's step it up a notch. With acetylene and ethyl the product shown. You may use any necessary Hiso.' 6. Given the fbllowing organic pieces, synthesizc thc product. Once again. you may Lrse any necessary rcascnts. z r) NaFl T z) tr1-sr rr1.,L- 'l ,r)t-\qH-P e)--\./\\cr 1.,,-I N ? 7. Synthesize 5,5,6,6-tetrabromo-3,4-dimethyl-3-hexanol from 3-methyl-2-pentene, using acetylene as your only additional carbon source. You may use any necessary reagents. z/-'.-r2oa l l | | - - - - . - - - - - - - - } \\/ "',/4// \*,, { o-,:.-Y-^f' 9,,o'.r br V3rl ll I o*l /" I 4** zu 8. Using acctylene as your only carbon source (are you noticing a pattern yet?!), perfbrm the following synthesis. Usc any neccssarv reaqents. Good luck! /-rZ L._\"u YLrz--F Ho-o 2 *Auzg...
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351 C11 Smith key - o let's step it up a notch With...

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