The following compounds are commercially available for use as water-soluble solvents. How could each be made? (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2}-\mathrm{O}-\mathrm{CH}_{2} \mathrm{CH}_{2}-\mathrm{O}-\mathrm{CH}_{2} \mathrm{CH}_{2}-\mathrm{OH}\) Carbitol (b) \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{O}-\mathrm{CH}_{2} \mathrm{CH}_{2}-\mathrm{O}-\mathrm{CH}_{2} \mathrm{CH}_{2}-\mathrm{OH} \quad\) Phenyl carbitol (c) \(\mathrm{HO}-\mathrm{CH}_{2} \mathrm{CH}_{2}-\mathrm{O}-\mathrm{CH}_{2} \mathrm{CH}_{2}-\mathrm{OH} \quad\) Diethylene gloycol (d) \(\mathrm{HO}-\mathrm{CH}_{2} \mathrm{CH}_{2}-\mathrm{O}-\mathrm{CH}_{2} \mathrm{CH}_{2}-\mathrm{O}-\mathrm{CH}_{2} \mathrm{CH}_{2}-\mathrm{OH}\) Triethylene glycol

Step by step solution

01

1. Synthesize Carbitol (#\(a\)#)

To synthesize Carbitol: \(\mathrm{CH}_{3} \mathrm{CH}_{2} - \mathrm{O} - \mathrm{CH}_{2} \mathrm{CH}_{2} - \mathrm{O} - \mathrm{CH}_{2} \mathrm{CH}_{2} - \mathrm{OH}\), we can use the Williamson ether synthesis, which involves the reaction of an alkoxide ion with an alkyl halide. In this case: 1. Prepare ethoxide ion from ethanol (\(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\)) and a strong base like sodium hydride (\(\mathrm{NaH}\)). 2. React the ethoxide ion with 2-chloroethyl ethyl ether (\(\mathrm{CH}_{3} \mathrm{CH}_{2} - \mathrm{O} - \mathrm{CH}_{2} \mathrm{CH}_{2} - \mathrm{Cl}\)) to form Carbitol.

02

2. Synthesize Phenyl carbitol (#\(b\)#)

To synthesize Phenyl carbitol: \(\mathrm{C}_{6} \mathrm{H}_{5} - \mathrm{O} - \mathrm{CH}_{2} \mathrm{CH}_{2} - \mathrm{O} - \mathrm{CH}_{2} \mathrm{CH}_{2} - \mathrm{OH}\), we can also use the Williamson ether synthesis. In this case: 1. Prepare phenoxide ion from phenol (\(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}\)) and a strong base like sodium hydride (\(\mathrm{NaH}\)). 2. React the phenoxide ion with 2-chloroethyl ethyl ether (\(\mathrm{CH}_{3} \mathrm{CH}_{2} - \mathrm{O} - \mathrm{CH}_{2} \mathrm{CH}_{2} - \mathrm{Cl}\)) to form Phenyl carbitol.

03

3. Synthesize Diethylene glycol (#\(c\)#)

To synthesize Diethylene glycol: \(\mathrm{HO} - \mathrm{CH}_{2} \mathrm{CH}_{2} - \mathrm{O} - \mathrm{CH}_{2} \mathrm{CH}_{2} - \mathrm{OH}\), we can follow these steps: 1. Start with the dehydration of ethylene glycol (\(\mathrm{HO} - \mathrm{CH}_{2} \mathrm{CH}_{2} - \mathrm{OH}\)), which produces ethylene oxide (\(\mathrm{CH}_{2} \mathrm{CH}_{2} - \mathrm{O}\)). 2. Open the ethylene oxide ring with the nucleophilic addition of ethylene glycol to form Diethylene glycol.

04

4. Synthesize Triethylene glycol (#\(d\)#)

To synthesize Triethylene glycol: \(\mathrm{HO} - \mathrm{CH}_{2} \mathrm{CH}_{2} - \mathrm{O} - \mathrm{CH}_{2} \mathrm{CH}_{2} - \mathrm{O} - \mathrm{CH}_{2} \mathrm{CH}_{2} - \mathrm{OH}\), we can follow these steps: 1. Start with the synthesis of Diethylene glycol (see step 3) and obtain ethylene oxide (\(\mathrm{CH}_{2} \mathrm{CH}_{2} - \mathrm{O}\)) and Diethylene glycol (\(\mathrm{HO} - \mathrm{CH}_{2} \mathrm{CH}_{2} - \mathrm{O} - \mathrm{CH}_{2} \mathrm{CH}_{2} - \mathrm{OH}\)). 2. Open the ethylene oxide ring with the nucleophilic addition of Diethylene glycol to form Triethylene glycol.

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