About reaction a.
You have the methyl-cyclohanol, why brominate it?
Why just do a Williamson ether synthesis using the alkoxide from the alcohol and react with the primary bromide, isobutylbromide?
I see! I get it, let me summarize the whole reactions then,
1. Oxidation - cyclohexanol is oxidized to form a ketone, cyclohexanone
2. Grignard reaction - using CH
3MgBr as Grignard reagent, methyl-cyclohexanol is produced
3. Preparing the alkoxide ion - react methyl-cyclohexanol with NaH to produce methyl-cyclohexide ion, Na
+ and H
2 4. Williamson ether synthesis - the alkoxide ion and isobutyl-bromide are reacted via alkyl halide's SN2 reaction to produce the product wanted.
Is that right?
I believe it is good pedagogy to use chemistry relevant to the discussion in a chapter. I think Bruice does a good job of that. If your instructor is extending the chemistry in some other manner, I wouldn't know about it. I tried to give an answer consistent with the chemistry of the early chapters.
Wow so true, that method actually helps a lot. Thanks so much. After seeing the explanation and referring to the book, I found everything in it. However, I did need to turn back and forth each pages, and when I realized, I had actually learned those chapters but I had not read deeper the subchapters (like hydration and Williamson ether synthesis). Guess I need to save some time to read the whole book myself
Obviously, I don't know what is being discussed in the class. If cyclohexyl methyl ketone had to be prepared from cyclohexanol, I might consider making a bromide from the alcohol and coupling it with a vinyl cuprate (I think this chemistry in Bruice?). Bromination-dehydrobromination would give cyclohexylacetylene. Hydration with sulfuric acid plus mercury salts would give the ketone.
I just read about coupling reactions, by coupling it with "vinyl cuprate", did you mean "vinyl lithium cuprate" (H
2CCH)
2CuLi? Can a Gilman reagent be acetylenyl lithium cuprate? So that it would give cyclohexylacetylene directly. And yet, I couldn't find explanation of bromination-dehydrobromination mechanism..