[pollution]

Hello, I have attempted transformations 1-5 of the 9 question worksheet and am wondering if they are correct.   I will attempt the other 4 questions and upload later.  I also have 2 other pages of predicting the product and mechanism I will attempt before uploading.   Thanks for any input.

[pollution]

Here answers 6-9.  I could not figure out #8 .

[movies]

Nice work, looks like most of them are right or at least on the right track.

In #2, using HCN directly doesn't really work, the two step way is a sure bet though. 

In #4, I think you have the wrong reagent.  NaBH₄ is usually used to reduce ketones and aldehydes to alcohols, it won't touch alkenes.  I think you probably meant to use a different boron reagent (Hint!).

For #5, you propose an S_N2 displacement on a tertiary carbon, which is a big no-no.  Think about the mechanism of the first step you proposed (where you add HBr).  How could you use a similar mechanism to make your product? (hint: 1 step!)

For #8, do you know any way to REDUCE a carbon to the alkane oxidation state?  There are a couple of ways to do it, but only one will give you only one D at the same position as the alcohol once was.

[tbuihuu]

my answer

[tbuihuu]

question 6: or 

[mdlhvn]

Yeah! wonderful answers of a future organic professor! 
Try your best.

[pollution]

Here are my final answers 

[movies]

5 is still wrong.

[pollution]

#5 is one of the right answers, there is more than one way to do it

[DaveD]

I think a better answer for 5 would be to react the starting material with H2SO4 instead of HBr, in MeOH as the solvent.  HSO4- is not as nucleophilic as Br- , and you should be able to trap the t-butyl cation with your MeOH to form your desired product MTBE.

[movies]

I think a better answer for 5 would be to react the starting material with H2SO4 instead of HBr, in MeOH as the solvent.  HSO4- is not as nucleophilic as Br- , and you should be able to trap the t-butyl cation with your MeOH to form your desired product MTBE.

Exactly!