Organic Chemistry Williamson Synthesis of an Ether

[imdapolak]

" Write an alternate reaction that can be used to prepare the same product that we got in our lab ( changing the metal in the alkoxide or halide leaving group is not sufficient.) Explain the reaction you used, is it expected to be cheaper cost wise, and or produce a higher yield, based on the physical properties of the reactants."
For the lab starting material we used para-chlorobenzyl chloride formula (C7H6Cl2) reacted with Sodium ( Na) + 1-propanol to get a chemical formula of C10H13OCL, which I am struggling to name but the prof suggested to just call it a Benzyl ether. My guess at the IUPAC name is para-chloro-benzyl-propoxy. The benzene ring has a cl at the para position, and at the meta there is a ch2-O-Ch2-Ch2-Ch3. I wrote out the Sn2 reaction for this problem but I am not sure how to write an alternate reaction to get the same product without using the same initial starting materials. I have been looking up other starting material compounds like benzyl chloride and cinnamyl chloride but I am not sure how to get chlorine in the para position, is there another reaction step I have to add to this? Any clarification on how to approach this problem would be greatly appreciated as my prof simply said "figure it out." Also, if anyone knows of a website that gives me the cost per mol of these starting materials that would be great, I am not sure how to look this up exactly.

Thanks in advance for any help

 

[Yanick]

This should be in HW help section but I'll give a hint.

Also you are overthinking the question. I doubt you're professor wants you to start completely from scratch (like benzene and propane). She just doesn't want you to change the Chloride to a Bromide or the Sodium to a Potassium (which is very trivial and doesn't serve to teach you anything about the Williamson Ether Synthesis).

Hopefully you've gone through this in lecture, or have heard of this concept before. If you haven't, now is a good time to read the page or two in your text about it. Its actually a lot simpler than it seems at first glance.

What is the 'jist' of the Williamson Ether synthesis?

Where in this 'jist' is the area of flexibility?