Catbonyl compounds

Pnctict Problem 19.1 What caTbonyl compound and what phosphorus ylide nu ht you use to prepare 3-cthyl-2-pentane ... 

Since water adds to (at least some) catbonyl compounds, it should come as no surprise that alcohols do too. The product of the reaction is known as a hcmiacetal, because it is halfway to an acetal, a functional group, which you met in Chapter 2 (p. 35) and which will be discussed in detail in Chapter 14. The mechanism follows in the footsteps of hydrate formation just use ROH instead of HOH. 

NR = nonreactive toward hydrocarbons PO — oxidation of phosphines to phosphine oxides MF — peroxometallacyclic adduct formation with cyanoalkenes NSE=nonstereoselective epoxidation SE-stereoselective epoxidation AE = asymmetric epoxidation HA-hydroxylation of alkanes HB=hydroxylation of arenes OA=oxidation of alcohols to carbonyl compounds K = ketonization of terminal alkenes SO — oxidation of SO to coordinated SO4 MO — metallaozonide formation with catbonyl compounds I — oxidation of isocyanides to isocyanates. 

Patents on the catbonylation of methyl chlotide [74-87-3] using carbon monoxide [630-08-0] in the presence of rhodium, palladium, and tidium complexes, iodo compounds, and phosphonium iodides or phosphine oxides have been obtained (26). In one example the reaction was conducted for 35... 

Stereoelectronic factors are also important in determining the stmcture and reactivity of complexes. Complexes of catbonyl groups with trivalent boron and aluminum compounds tend to adopt a geometry consistent with directional interaction with one of the oxygen lone pairs. Thus the C—O—M bond angle tends to be in the trigonal (120-140°) range, and the boron or aluminum is usually close to die carbonyl plane. ... 

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