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 MgBr diethyl ether I-Bromocyclohexene 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 I-hexanolate CHa CH, CH,CH,CH,CH,OH CHCH,CH,CH,Li CH3 CH,, CH3 CHCH,CH, CH,CH, CH,OLi 1-Hexanol Butyllithium Butane Lithium 1-hexanolate (c) The proton donor here is benzenethiol. C6HSSH CH,CHCH,CH,Li CH, CHCHCH ChSLi Benzenethiol Butyllithium Butane Lithium 14.5(b) Propylmagnesium bromide reacts with benzaldehyde by addition to the carbonyl group CHI CH2CH2T-MgBr CHCHCH diethyl ether C6H CTO C6HSC-OMg Br C6HSCHCH,CH,CH 1-Phenyl-1-but (c) Tertiary alcohols result from the reaction of Grignard reagents and ketones CHCHCI CHa CH,CH,Mg Br 1-Propylcyclohexanol (d) The starting material is a ketone and so reacts with a Grignard reagent to give a tertiary alcohol H,CH,CH2-MgE H C CH, CHCH diethyl ether CHaCH,CH,CO CHa CH, Propylmagnesium bromide 3-Methyl-3-hexanol Back Forward Main Menu TOC Study Guide Toc Student OLC MHHE Website(d) Bromine is attached to an sp2 -hybridized carbon in 1-bromocyclohexene. The product of its reaction with magnesium has a carbon–magnesium bond in place of the carbon–bromine bond. 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. (c) The proton donor here is benzenethiol. 14.5 (b) Propylmagnesium bromide reacts with benzaldehyde by addition to the carbonyl group. (c) Tertiary alcohols result from the reaction of Grignard reagents and ketones. (d) The starting material is a ketone and so reacts with a Grignard reagent to give a tertiary alcohol. diethyl ether H3O CH3CH2CH2 H3C C OMgBr CH3CH2 3-Methyl-3-hexanol CH3CH2CH2COH CH2CH3 CH3 CH3CH2CH2 MgBr O CH3CH2 C H3C Propylmagnesium bromide 2-butanone 1. diethyl ether 2. H3O CH3CH2CH2MgBr O CH2CH2CH3 OH 1-Propylcyclohexanol diethyl ether H3O C6H5C O H CH3CH2CH2 C6H5C OMgBr H 1-Phenyl-1-butanol C6H5CHCH2CH2CH3 OH CH3CH2CH2 MgBr C6H5SH Benzenethiol C6H5SLi Lithium benzenethiolate CH3CH2CH2CH2Li Butyllithium CH3CH2CH2CH3 Butane CH3CH2CH2CH2CH2CH2OH 1-Hexanol CH3CH2CH2CH2CH2CH2OLi Lithium 1-hexanolate CH3CH2CH2CH2Li Butyllithium CH3CH2CH2CH3 Butane Mg diethyl ether 1-Bromocyclohexene Br 1-Cyclohexenylmagnesium bromide MgBr ORGANOMETALLIC COMPOUNDS 343 Back Forward Main Menu TOC Study Guide TOC Student OLC MHHE Website