The reaction of alkoxides with haloalkanes is not a viable way to form ethers. (a) Why? (b) Why can thioethers be formed by an analogous reaction?

Mullins 1st Edition
Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination
Problem 104aSuggest a synthesis for the following molecules beginning with organic molecules containing three or fewer carbons. [You will need to use a protecting group in these syntheses.]
(a) 
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Key Concepts
Synthesis Strategy
Protecting Groups
Functional Group Interconversion
Suggest a synthesis for the following molecules beginning with organic molecules containing three or fewer carbons. [You will need to use a protecting group in these syntheses.]
(c)
In contrast to Assessment 13.102, only one combination of haloalkane and alkoxide can be used in the Williamson ether synthesis to make the ether shown. Identify the combination and explain why it is the only combination that works.
Identify the two possible combinations of haloalkane and alkoxide that can be used to make the following ether.
Suggest a synthesis for the following molecules beginning with organic molecules containing three or fewer carbons. [You will need to use a protecting group in these syntheses.]
(b)
Draw a mechanism for the following oxidation reactions.
(d)