Ch15 - 310 S olutions C hapter 15 O rganometallic Compounds 311 S olutions Chapter 15 O rganometallic Compounds.emblem 15.4 Show h ow to prepare

Info iconThis preview shows pages 1–3. Sign up to view the full content.

View Full Document Right Arrow Icon
------ 310 Solutions. Chapter 15: Organometallic Compounds CHAPTER 15 Solutions to the Problems Problem l5.l Explain how these Grignard reagents would react with molecules of their own kind to "self-destruct". Grignard reagents are strong bases. In both cases the Grignard reagent will "self·destruct" due to an aCid-base reaction. ..' '. (a) H~rvgBr HO~M9Br' (M9Br)+-~ (b)~rvgBr -------- (MgEt)+';~· Problem 15.2 Recalling the reactions of alcohols from Chapter 10, show how to synthesize each compound from an organohaloge~ ~ompoun.d and an oxirane. followed by a transformation of the resulting hydroxyl group to the desired .oxygen-contammg functional group. o 0 (a)~ B.r ()M9Br p\ . Mg 1. L..... :). ~OH ~O () ether .. .-2-.-H-C-I-/-H .... :~O (b) ~o ' OH . PCC . ~O or U"Y -- K 2 Cr 207 H 2 S0 4 H 2 0, heat Problem 15.3 Show how to bring about each conversion using a lithium diorganocopper reagent. (a) U' + (CH,CH,CH,CH,),CuLi - ...... - I .# ~ ~B.r+ (b) V ((CH 3 hCHCH 2 hCuLi Solutions 311 Chapter 15: Organometallic Compounds .emblem 15.4 Show how to prepare each Gilman reagent in Example 15.4 from an appropriate alkyl halide and each epoxide from an appropnate alkene. . 2Li . . FC0 3 H ~ C ~ C~ Br - ~CH:2Li+ LiBr CsHs~ ~ CsHs' . . I '3 ''2 (racemIc) CuI ~* .. 2 C~CH:2Li - [(C~C~hCu]U+ LIT ~FC03~~ (~emic) or alternatively, 2Li Cs H s C~ Li + LiBr CsHsC~Br Cui ---'''~ [( CsHsCH:2hCu]Li + Lil Emblem 15.5 Predict the product of the following reaction. !'k--~~ (}=CH 2 + + ~ ~. Elr Problem 15.6 Show how the following compound could be prepared from any compound con~ining ten carbons or fewer. y '1<J ' OH Zn(Cu) y' OH. . + C~212 ... diethyl ether Y Emblem 15.7 Complete these reactions involving lithium diorganocopper (Gilman) reagel1ts. (a) Q-Br + ( )r,CULi "h'" 0-< + LiBr rY Br 0+ .. ",.-. (b) (~CULi ether 2 '. ~Cu + UBr' ~ (C)~I + . (7t,CULi .. ether -t- eu +. u,
Background image of page 1

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

View Full DocumentRight Arrow Icon
313 Chapter 15: Organometallic Compounds Solutions 312 Solutions Cbapter 15: Organometallic Compounds t~ (d) " (~CULi .. . . 2 ether CX+ ~ Cu . + LiCI problem 15.8 Show how to convert I-bromopentane to each ofthese compounds using a lithium diorganocopper (Gilman) reagent. Write.an equation, showing structural formulas, for each synthesis. . (a) Nonane CH3CH2CH2CH2CH2Br + (CH 3 CH 2 C-H 2 CH 2 hCuLi ether ~ CH 3 (CH 2 hCH 3 · + CH 3 CH 2 CH 2 CH 2 Cu + LiBr Nonane (b) 3-Methyloctane ~C~C~~C~Br ether 0i 3 I. ~3 ~CH2OiC~CftzC~~~ + + UBr ~C~OiCu 3-Methyloctane Note how the 3-methyloctane has one chiral center, so a racemic mixture will be produced assuming the Gilman reagent starting material i~ racemic: (c) 2,2-Dimethylheptane CH3CH2CH2CH2CH2Br +. [(CH 3 hChCuLi -e-t-he-r-i·" CH 3 I CH3yCH2CH2CH2CH2CH3 + + LiBr CH 3 . 2,2-Dimethylheptane (d) I-Heptene .. CH3CH2CH2CH2CH2Br . + (CH 2 =CHhCuLi ether + LiBr + I-Heptene (e) l-Octene. CH3CH2CH'2CH2CH2Br
Background image of page 2
Image of page 3
This is the end of the preview. Sign up to access the rest of the document.

This note was uploaded on 07/09/2011 for the course CHE 301 taught by Professor Diver during the Spring '08 term at SUNY Buffalo.

Page1 / 6

Ch15 - 310 S olutions C hapter 15 O rganometallic Compounds 311 S olutions Chapter 15 O rganometallic Compounds.emblem 15.4 Show h ow to prepare

This preview shows document pages 1 - 3. Sign up to view the full document.

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