Primary alcohols haloalkanes from

Modifying the reaction medium to involve liquid ammonia with metallic lithium, f-butyl alcohol, and white phosphorus, to which is added the haloalkane, is reported to provide the primary alkylphos-phine derived from the haloalkane.19 Similar results are reported for the reaction of red phosphorus with sodium acetylides20 and by treatment of red phosphorus with sodium metal in an organic medium followed by the addition of two equivalents of f-butyl alcohol and the haloalkane.21 The latter approach is noteworthy in that moderate yields (45%) are obtained for primary phosphines derived from secondary haloalkanes (Figure 2.6). Mixtures of tertiary phosphines bearing one or two acetylenic linkages are produced in low yield ( 15%) by the reaction of lithium acetylides with white phosphorus in liquid ammonia followed by addition of a haloalkane.22... 

Haloalkanes from primary alcohols and HX Water can be a leaving group in 5, 2 reactions... 

Let us inspect these transformations in greater detail. In reaction 1, a hydroxide ion, typically derived from sodium or potassium hydroxide, displaces chloride from chloromethane to give methanol. This substitution is a general synthetic method for converting a methyl or primary haloalkane into an alcohol. 

Alkyl phenyl ethers are prepared by the WUhamson synthesis (Section 16.6). In these reactions a phenoxide ion displaces a halide ion from a primary haloalkane. Because alcohols are weak acids, an alkoxide ion must be prepared using a strong base such as sodium hydride. However, phenols are much more acidic than alcohols, so phenoxides can be obtained by adding hydroxide ion to the phenol. 

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