Baixe Carey - Organic Chemistry - sgchapt14 e outras Manuais, Projetos, Pesquisas em PDF para Química, somente na Docsity! CHAPTER 14 ORGANOMETALLIC COMPOUNDS SOLUTIONS TO TEXT PROBLEMS 14.1 (b) Magnesium bears a cyclohexyl substituent and a chlorine. Chlorine is named as an anion. The compound is cyclohexy Imagnesium chloride. 14.2 (b) The alkyl bromide precursor to sec-butyllithium must be sec-butyl bromide. CH,CHCH,CH, + LiBr CHGHCHCH, + 2Li Br Li 2-Bromobutane 1-Methylpropy lithium (sec-butyI bromide) (see-butyllithium) 14.3 (b) Allyl chloride is converted to allylmagnesium chloride on reaction with magnesium. Mg H,C=CHCH Cl mçiemer H,C==CHCH,Mgcl Allyl chloride Allylmagnesium chloride (c) | The carbon-iodine bond of iodocyclobutane is replaced by a carbon-magnesium bond in the Grignard reagent. I Mgl ( do diethy ether Iodocyclobutane Cyclobutylmagnesium iodide 342 Back) Forward Main Menul Toc] Study Guide TOC Student OLC MHHE Website ORGANOMETALLIC COMPOUNDS 343 (d) Bromine is attached to an sp?-hybridized carbon in 1-bromocyclohexene. The product of its reaction with magnesium has a carbon-magnesium bond in place of the carbon-bromine bond. Br MgBr Mg CY diethy ether CY 1-Bromocyclohexene 1-Cyelohexenylmagnesium bromide 14.4 (b) 1-Hexanol will protonate butyllithium because its hydroxyl group is a proton donor only slightly less acidic than water. This proton-transfer reaction could be used to prepare lithium 1-hexanolate. CH,CH,CH,CH,CH,CH,0H + CH;CH,CH,CH,Li —— CH;CH,CH,CH, + CH;CH,CH,CH,CH,CH,OLi 1-Hexanol Butyllithium Butane Lithium |-hexanolate (c) The proton donor here is benzenethiol. CHSH + CHCHCHCHLi —— CHCHCHCH, + CHSLi Benzenethiol Butyllithium Butane Lithium benzenethiolate 14.5 (b) PropyImagnesium bromide reacts with benzaldehyde by addition to the carbonyl group. CH.CH,CH,=-MgBr ! CH,CH,CH, diethyl ether HO“ CMÉTO De, Cof OMgBr — > CH,CHCH,CH,CH, H H oH 1-Phenyl-1-butanol (c) | Tertiary alcohols result from the reaction of Grignard reagents and ketones. 1. diethyl ether, CH,CH,CH, CH.CH,CH,MgBr + O eo» q 2H 1-Propyleyelohexanol (d) The starting material is a ketone and so reacts with a Grignard reagent to give a tertiary alcohol. CH,CH,CH,—MgBr c CH,CH,CH, cH, x Co Setter, o tOMgBr — LL, CHCHCH,COH CH;CH, CH.CH, CH;CH, Propylmagnesium bromide 3-Methyl-3-hexanol + 2-butanone MainMenu) TOC] StudyGuideTOC| Student OLC| | MHHE Website 346 14.14 14.15 14.16 Back| Forward ORGANOMETALLIC COMPOUNDS (d) Lithium divinylcuprate has two vinyl groups bonded to copper. It is an organometallic compound. Li“(H,C=CH—Cu—CH=CH,) (e) - Sodium carbonate, Na,CO, can be represented by the Lewis structure. There is no carbon-metal bond, and sodium carbonate is not an organometallic compound. (/) Benzylpotassium is represented as (cn or (Sê, Kt It has a carbon-potassium bond and thus is an organometallic compound. The two alkyl groups attached to aluminum in [(CH;),)CHCH,], AIH are isobutyl groups. The hy- drogen bonded to aluminum is named in a separate word as hydride. Thus, “dibal” is a shortened form of the systematic name diisobutylaluminum hydride. (a) Grignard reagents such as pentylmagnesium iodide are prepared by reaction of magnesium with the corresponding alkyl halide. diethyl ether 2 CH,CH.CH,CH,CH,I + Mg CH,CH,CH,CH,CH,Mgl |-lodopentane Pentylmagnesium iodide (b) | Acetylenic Grignard reagents are normally prepared by reaction of a terminal alkyne with a readily available Grignard reagent such as an ethy Imagnesium halide. The reaction that takes place is an acid-base reaction in which the terminal alkyne acts as a proton donor. diethyl ether a CH,CH,C=CH + CH,CH,Mgl CH,CH,C=CMgl + CH.CH, 1-Butyne Ethylmagnesium 1-Butynylmagnesium Ethane iodide iodide (c) — Alkyllithiums are formed by reaction of lithium with an alkyl halide. CH,CH,CH,CH,CH,X + 2Li CH,CH,CH,CH,CH,Li + LiX 1-Halopentane Pentyllithium (X=C1, Brorl) (d) Lithium dialkylcuprates arise by the reaction of an alkyllithium with a Cu(T) salt. 2CH,CH;CH,CH,CHLi + CuX — — LiCu(CH,CH,CH,CH,CH;), + LiX Pentyllithium, from part (c) (X=C1, Bror1) Lithium dipentylcuprate The polarity of a covalent bond increases with an increase in the electronegativity difference be- tween the connected atoms. Carbon has an electronegativity of 2.5 (Table 14.1). Metals are less elec- tronegative than carbon. When comparing two metals, the less electronegative one therefore has the more polar bond to carbon. (a) Table 14.1 gives the electronegativity of lithium as 1.0, whereas that for aluminum is 1.5. The carbon-lithium bond in CH;CH,Li is more polar than the carbon-aluminum bond in (CH,CH,),AL. MainMenu) TOC] StudyGuideTOC| Student OLC| | MHHE Website ORGANOMETALLIC COMPOUNDS 347 (b) (c) 1417 (a) (b) (c) (d) (e) 1 (8) dy) (1) Og The electronegativity of magnesium (1.2) is less than that of zinc (1.6). (CH;),Mg therefore has a more polar carbon-metal bond than (CH,;),Zn. In this part of the problem two Grignard reagents are compared. Magnesium is the metal in both cases. The difference is the hybridization state of carbon. The sp-hybridized carbon in HC=CMgBr is more electronegative than the sp*-hybridized carbon in CH,CH,MgBr, and HC==CMgBr has a more polar carbon-magnesium bond. . dieihyleher . . CH.CH,CH;Br + 2Li TE, cH,CH,CH,Li + LiBr 1-Bromopropane Propyllithium CH.CH,CH;Br + Mg SEL, cH,CH,CH;MgBr 1-Bromopropane Propylmagnesium bromide CH,CHCH, + 2Li ER, cHCHCH, + Lil I Li 24odopropane Isopropyllithium diethyl ether > CHÇHCH; + Mg CH,CHCH, I Mgl 2-1odopropane Isopropylmagnesium iodide 2CH,CH,CH,Li + Cul —— (CH,CH.CH,,Culi Propyllithium Lithium dipropylcuprate (CH.CH,CH,);CuLi + CH,CH,CH;CH;Br ——» CH,CH,CH,CH,CH,CH,CH, Lithium dipropylcuprate 1-Bromobutane Heptane I CH,CH,CH, cemsenemoscus + (OT —— CY Lithium dipropylcuprate Todobenzene Propylbenzene D;O CH;CH,CH,MgBr —— CH;CH,CH;D Propylmagnesium 1-Deuteriopropane bromide D;O CHiCHCH; —a— CHCHCH; Li D Isopropyllithium 2-Deuteriopropane . | 1. diethyl ether CH;CH,CHyLi + HCH o > CH;CH,CH;CH,OH 4 Propyllithium 1-Butanol Back) Forward] MainMenu] TOC] StudyGuide TOC] —StudentOLC| | MHHE Website 348 14.18 Back| Forward ORGANOMETALLIC COMPOUNDS o | (k CH.;CH,CH;MgBr + (Sem TOR (qnencnen, BET OH Propylmagnesium Benzaldehyde 1-Phenyl-I-butanol bromide (1) CHHCH, + Li Õ (CHyCH OH Isopropyllithium Cycloheptanone 1-Isopropyleycloheptanol o oH | | dieihyl ether Í (m) CHÇHCH, + CHCCHCH, So CHÇH—ÉCHCH, 2H Mgl cH, CH, Isopropyl- 2-Butanone 2,3-Dimethyl-3-pentanol magnesium iodide 0H | 1. diethyl ether (1) 2CHCHCHMgBr + CHCOCH, Sor CH.C(CH,CH.CH,;), + CH,0H Propylmagnesium Methyl benzoate 4-Phenyl-4-heptanol Methanol bromide CHA, (0) HC=CH(CH)CH, SiroanaiaR” HG EHCHo.CH, tm, 1-Octene 1-Cyclopropylhexane HC H » Ê “e= Rá CH P. — N Zu(Cu), diethyl ether né (CH.CH, (CH)CH, (E)-2-Decene trans-1-Heptyl-2- methyleyclopropane CH,CH, (CH;),CH Re OO am CHCH DS a(CHO,CH, (9) PTN Zn(Cu), diethyl ether à, H H H H (2)3-Decene cis-1-Ethyl-2-hexyl- cyclopropane Br Br CHB: (7) H,C=CHCH,CH,CH, TocCHT” CH,CH.CH, HH 1-Pentene 1 1-Dibromo-2-propyleyelopropane In the solutions to this problem, the Grignard reagent butylmagnesium bromide is used. In each case the use of butyllithium would be equally satisfactory. MainMenu) TOC] StudyGuideTOC| Student OLC| | MHHE Website ORGANOMETALLIC COMPOUNDS 351 (c) The desired product is a secondary alkyl bromide. A reasonable synthesis would be to first prepare the analogous secondary alcohol by reaction of pheny Imagnesium bromide with benz- aldehyde, followed by a conversion of the alcohol to the bromide. Retrosynthetically this can be seen as Br oH o | I | CHCH—CH, > cHCH+CH, > C;HMgX + CHCH Or AO) dee gi) em ad) 0H Br Phenylmagnesium Benzaldehyde Diphenylmethanol Bromodiphenylmethane bromide (d) The target molecule is a tertiary alcohol, which requires that pheny Imagnesium bromide react with a ketone. By mentally disconnecting the phenyl group from the carbon that bears the hydroxyl group, we see that the appropriate ketone is 4-heptanone. po f A CH,CH,CH.CCH,CH,CH, > CH,CH,CH,CCH.CH,CH, + Ó 4-Phenyl-4-heptanol 4-Heptanone The synthesis is therefore MgBr f 0H 1 Cr + CH;CH,CH,CCH,CH,CH, >» CH,CH,CH,CCH;CH,CH, Phenylmagnesium 4-Heptanone 4-Phenyl-4-heptanol bromide (e) Reaction of phenylmagnesium bromide with cyclooctanone will give the desired tertiary alcohol. gBr O Ae diethytether + 2H00 Phenylmagnesium — Cyclooctanone 1-Phenyleyelooctanol bromide (f) The 1-phenylcyclooctanol prepared in part (e) of this problem can be subjected to acid- catalyzed dehydration to give 1-phenylcyclooctene. Hydroboration-oxidation of 1-phenyl- cyclooctene gives trans-2-pheny lcyclooctanol. m O H;SO,, heat hH H ra oH 1-Phenyleyelooctanol 1-Phenyleyclooctene trans-2-Phenyleyelooctanol Back) Forward] MainMenu] TOC] StudyGuide TOC] —StudentOLC| | MHHE Website 352 ORGANOMETALLIC COMPOUNDS 14.20 | In these problems the principles of retrosynthetic analysis are applied. The alkyl groups attached to the carbon that bears the hydroxyl group are mentally disconnected to reveal the Grignard reagent and carbonyl compound. Doo (a) CH CH FCHACHICH(CHy, oH 5-Methyl-3-hexanol Do O CH.CH;MgX + HÇCHCHCHy» CEICHqa + XMgCH,CH(CH;), 0 Ethylmagnesium 3-Methylbutanal Propanal Isobutylmagnesium halide halide (b) «1 (2 Dont Socn, 0H 1-Cyclopropyl-I-(p-anisylmethano! >— Mex + ne Soocn, Dea + xmM A Som TI | e : o O Cyclopropyl- p-Anisaldehyde Cyclopropane- p-Anisylmagnesium magnesium halide carbaldehyde halide o Í () — (CH)CCH,0H > (CH),CMgX + HCH 2,2-Dimethyl-1-propanol tert-Butylmagnesium Formaldehyde halide (d) (1) 2 (CH C=CHCH,CH,HCH-CH, OH 6-Methyl-5-hepten-2-ol (CH)C=CHCH,CH,MgX + HECH, (CH C=CHCHLCHLÇH + XMgCH, 4-Methyl-3-hexen-1-ylmagnesium Ethanal 5-Methyl-4-hexenal Methylmagnesium halide halide Back) Forward] MainMenu] TOC] StudyGuide TOC] —StudentOLC| | MHHE Website Back| ORGANOMETALLIC COMPOUNDS 353 (e) D E e E DM + oH 4Ethyl.4-octanol Propylmagnesium halide 3-Heptanone NO + XMg uq ó O + XMg ON 4-Octanone Ethylmagnesium 3-Hexanone Butylmagnesium halide halide 14.21 (a) Meparfynol is a tertiary alcohol and so can be prepared by addition of a carbanionic species to a ketone. Use the same reasoning that applies to the synthesis of alcohols from Grignard reagents. On mentally disconnecting one of the bonds to the carbon bearing the hydroxyl group qu Pai CHCHC=CH CHcH =“C=CH CH CH 3 3 we see that the addition of acetylide ion to 2-butanone will provide the target molecule. o oH I 1.NH, | HC=CNa + CHCH,CCH, — o CH,CH,CC=CH 2H cH, Sodium 2-Butanone Meparfynol (94%) acetylide The alternative, reaction of a Grignard reagent with an alkynyl ketone, is not acceptable in this case. The acidic terminal alkyne C—H would transfer a proton to the Grignard reagent. (b) | Diphepanol is a tertiary alcohol and so may be prepared by reaction of a Grignard or organo- lithium reagent with a ketone. Retrosynthetically, two possibilities seem reasonable: Ge CH; (Cota ÇCH—N ) > CHS + CRLGCH=N oH o and Ge Gs (CoHoÇCH—N ) > (CHAC=0 + ICHN 5 oH Forward] MainMenu| TOC] Study Guide TOC] StudentOLC| — MHHE Website] 356 ORGANOMETALLIC COMPOUNDS Dehydration of either alcohol yields 4-tert-butyl-1-phenylcyclohexene. H H H recto o o See Heat Neem ci CoHs 4-tert-Butyl-I-phenyleyclohexene 14.24 (a) By working through the sequence of reactions that occur when ethyl formate reacts with a Grignard reagent, we can see that this combination leads to secondary alcohols. I 1. RMgX, diethyl ether RCH + CH,CHOMgXx TST, ReHR I RMgX + HCOCH,CH, 2.H,0' | oH Grignard Ethyl formate Aldehyde Secondary reagent alcohol This is simply because the substituent on the carbonyl carbon of the ester, in this case a hydrogen, is carried through and becomes a substituent on the hydroxyl-bearing carbon of the alcohol. (b) | Diethyl carbonate has the potential to react with 3 moles of a Grignard reagent. o I RCOCH.CH, + CH;CH,OMgX | RMgX + CH,CH,OCOCH,CH, Grignard Diethyl Ester reagent carbonate RMgX i Í RR EX RCR + CH,CH,OMgX OH Tertiary alcohol Ketone The tertiary alcohols that are formed by the reaction of diethyl carbonate with Grignard reagents have three identical R groups attached to the carbon that bears the hydroxyl substituent. 14.25 If we use the 2-bromobutane given, along with the information that the reaction occurs with net inversion of configuration, the stereochemical course of the reaction may be written as cH,CH, CH; CH. 2 LiCUC Ho H É ss Lica, com A cHCH, H The phenyl group becomes bonded to carbon from the opposite side of the leaving group. Applying the Cahn-Ingold-Prelog notational system described in Section 7.6 to the product, the order of decreasing precedence is CH,>CH;CH,>CH,>H Back) Forward] MainMenu] TOC] StudyGuide TOC] —StudentOLC| | MHHE Website ORGANOMETALLIC COMPOUNDS 357 Orienting the molecule so that the lowest ranked substituent (H) is away from us, we see that the order of decreasing precedence is clockwise. CH HCÉ CH:CH, The absolute configuration is R. 14.26 The substrates are secondary alkyl p-toluenesulfonates, and so we expect elimination to compete with substitution. Compound B is formed in both reactions and has the molecular formula of 4-tert-butylcyclohexene. Because the two p-toluenesulfonates are diastereomers, it is likely that compounds A and C, especially since they have the same molecular formula, are also diastereomers. Assuming that the substitution reactions proceed with inversion of configuration, we conclude that the products are as shown. cH, SET LiCUCH;, SJ 4 (CH):€ (CH);€ (CH;;€ trans-4-tert-Butyleyclohexyl cis-1-tert-Butyl-4-methyleyclohexane | 4-tert-Butylcyclohexene poluenesulfonate (compound A, €, H,) (compound B, C His) OTs LiCuCH;), SETE MeucH » O 2 (CHAO + (CH);€ cis-4-tert-Butyleyclohexyl trans-1-teri-Butyl-4-methyleyclohexane Compound B p-toluenesulfonate (compound C, CH.) Inversion of configuration is borne out by the fact given in the problem that compound C is more stable than compound A. Both substituents are equatorial in C; the methyl group is axialin A. 14.27 We are told in the statement of the problem that the first step is conversion of the alcohol to the cor- responding p-toluenesulfonate. This step is carried out as follows: cH, o 0H o OTs so,Ci 3,8-Epoxy-1-undecanol p-Toluenesultonyl 3.8-Epoxyundecyl chloride (TsCI) p-toluenesulfonate Alkyl p-toluenesulfonates react with lithium dialkylcuprates in the same way that alkyl halides do. Treatment of the preceding p-toluenesulfonate with lithium dibutylcuprate gives the desired compound. o OTs o 3,8-Epoxyundecyl 4,9-Epoxypentadecane poluenesulfonate Back) Forward] MainMenu] TOC] StudyGuide TOC] —StudentOLC| | MHHE Website 358 ORGANOMETALLIC COMPOUNDS As actually performed, a 91% yield of the desired product was obtained in the reaction of the p-toluenesulfonate with lithium dibutylcuprate. 14.28 (a) The desired 1-deuteriobutane can be obtained by reaction of D,O with buty lithium or butyl- magnesium bromide. cH,CH,CH,CHLi + D,O Butyllithium Deuterium oxide CH,CH,CH,CH,D or 1-Deuteriobutane CH,CH,CH,CH,MgBr + D,O Butylmagnesium bromide Preparation of the organometallic compounds requires an alkyl bromide, which is synthesized from the corresponding alcohol. PB; CH,CH.CH,CH,0H — q CH,CH,CH.CH;Br 1-Butanol 1-Bromobutane Li M; CH,CH,CH,CH,Li = CH.CH;CHCHBr — CH,CH,CH,CH,MgBr Butyllithium 1-Bromobutane Butylmagnesium bromide (b) In a sequence identical to that of part (a) in design but using 2-butanol as the starting mate- rial, 2-deuteriobutane may be prepared. PB; Mg DO CHCHCH,CH, —— CHACHCH:CH, —— CHAGHCH:CH, —— CHGHCHCH; OH Br MgBr D 2-Butanol 2-Bromobutane sec-Butylmagnesium 2-Deuteriobutane bromide An analogous procedure involving sec-butyllithium in place of the Grignard reagent can be used. 14.29 All the protons in benzene are equivalent. In diphenyImethane and in tripheny Imethane, protons are attached either to the sp?-hybridized carbons of the ring or to the sp”-hybridized carbon between the rings. The large difference in acidity between diphenyImethane and benzene suggests that itis not a ring proton that is lost on ionization in diphenyImethane but rather a proton from the methylene group. (CH9CH, (CHE + H* Diphenylmethane The anion produced is stabilized by resonance. It is a benzylic carbanion. GO — HO — e Back) Forward] MainMenu] TOC] StudyGuide TOC] —StudentOLC| | MHHE Website ORGANOMETALLIC COMPOUNDS 361 A-6. Show by a series of chemical equations how you would prepare octane from 1-butanol as the source of all its carbon atoms. A-7. Synthesis of the following alcohol is possible by three schemes using Grignard reagents. Give the reagents necessary to carry out each of them. qu (CH; CHO(CH3), A-8. Using ethylbenzene and any other necessary organic or inorganic reagents, outline a synthe- sis of 3-phenyl-2-butanol. Give the structure of the final product of each of the following sequences of reactions. o a) O e me cada, no FeBr, ' Í . () IButene —, Me, mm not, =0 NaNH, Hr (e) CHC=CH AM, ss, ss PART B B-1. Which (if any) of the following would not be classified as an organometallic substance” (a) Triethylaluminum (b) EthyImagnesium iodide (c) | Potassium tert-butoxide (d) |. None of these (all are organometallic compounds) B-2. Rank the following species in order of increasing polarity of the carbon-metal bond (least —> most polar): CH,CH,MgCl CH;CH,Na (CH,CH);AI 1 2 3 (a) 3<1<2 6) 2<1<3 () 1<3<2 (d) 2<3<1 B-3. Which sequence of reagents would carry out the following conversion? CHCH.ÇHCH, — CH.CH.CHCH, 0H D (a) -H;SO,, heat; then B,Ds; then H,O0,, HO” (b) HSO,, heat; then D,, Pt (c) - CH;MgBr; then DO (d) HBr; then Mg: then DO B-4. Arrange the following intermediates in order of decreasing basicity (strongest — weakest): H,C=CHNa CH,CH,Na CH,CH,ONa — HC=CNa 1 2 3 4 (a) 2>1>4>3 () 3>4>1>2 (b) 4>1>2>3 (d) 3>2>4>1 Back) Forward] MainMenu] TOC] StudyGuide TOC] —StudentOLC| | MHHE Website 362 Back| B-5. B-6. B-8. ORGANOMETALLIC COMPOUNDS Which, if any, of the following pairs of reagents could be used to prepare 2-phenyl- 2-butanol? qu CHCHÇOHs cH, 2-Phenyl-2-butanol | (a) CH;CH;MgBr + CH,CH,CCH, | (b) CH,CH,MgBr + CH,CH,CH | (c) CHMgl + CHCH,CCH, i (d) CHHMgcl + CH,CCH,CH,CH, (e) None of these combinations would be effective. Which of the following reagents would be effective for the following reaction sequence”? 1? 2.H,C=0 CHC=CH So CHC=CCH,0H E (a) - Sodium ethoxide (c) Butyllithium (b) | Magnesium in diethyl ether (d) Potassium hydroxide What is the product of the following reaction? + 2CHM 1. diethyl ether, 5MgBr so” o” So (a) HOCHCH,CHLCH,CHOH (o) CHOCH;CH;CHCH,CHCH; cH, cH, OH q (b) HOCH,CH.CH,CHÇOH (d) HOCH,CH.CH,CH.CHOCH, cH, cH, Which of the following combinations of reagents will yield a chiral product after hydrolysis in aqueous acid? o o (a) As + CH;MgBr (o) cucufoca, + 2CH;MgBr o (b) A + CH;MgBr (d) Both (a) and (e) Forward] MainMenu| TOC] StudyGuideTOC| StudentOLC| | MHHE Website Back| Forward ORGANOMETALLIC COMPOUNDS 363 B-9. B-10. Which sequence of steps describes the best synthesis of 2-phenylpropene”? (a) -Benzene + 2-chloropropene, AICL, (b) -Benzene + propene, H;SO, (c) 1. Benzaldehyde (CH;CH=0) + CH;CH,MgBr, diethyl ether 2. HO! 3. HSO,, heat (d) 1. Bromobenzene + Mg, diethyl ether 2. Propanal (CH;CH,CH=0) 3. HO! 4. HySO,, heat (e) 1. Bromobenzene + Mg, diethyl ether 2. Acetone [(CH;),C=0)] 3. HO! 4. HySO,, heat What sequence of steps represents the best synthesis of 4-heptanol (CH;CH,CH,),CHOH? (a) -CH;CH,CH,MgBr (2 mol) + formaldehyde (CH,=0) in diethyl ether followed by HO* (b) CH;CH,CH,MgBr + butanal (CH,CH,CH,CH=0) in diethyl ether followed by HO* (c) - CH;CH,CH,CH,MgBr + acetone [(CH;),C—0] in diethyl ether followed by H,0* (d) (CH;CH,CH,),CHMgBr + formaldehyde (CH;—=0) in diethyl ether followed by HO* | (e) CH,CH,CH,MgBr + ethyl acetate (CH;COCH.CH, ) in diethyl ether followed by HO « All of the following compounds react with ethyImagnesium bromide. Alcohols are formed from four of the compounds. Which one does not give an alcohol? í í í (a) CH (c) ( S-toem, (e) ( S-enoten, Í i (b) CcoH (d) CCH, - Give the major product of the following reaction: CHA, Zn(Cu) (E)-2-pentene —>>>—» (a) cis-1-Ethyl-2-methylcyclopropane (b) trans-1-Ethyl-2-methylcyclopropane (c) — 1-Ethyl-I-methylcyclopropane (d) | An equimolar mixture of products (a) and (b) MainMenu) TOC] StudyGuideTOC| Student OLC| | MHHE Website