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t.cengagenow.com/ilrn/takeAssignment/takeCovalentActivity.do?locator assignment take&takeAssig; nment SessionLocator assignment-take Select the reagents you would use to synthesize the compound below fiom benzene Use the minimum number of steps. No more than four steps are required List the letters of the reagents in the order dat they are used example fa CHBr CH2CH3 Reagents Available a. Br FeBr3 i CH3CH2COCI, AlCl3 b. Cl2. FeCla j, bromosuccinimide (NBS). (PhCO202 C. KOH g, Hz. Pd k. BHs. THF; then H202, OH Reagents used

Explanation / Answer

Hi, the compound you want to synthesize has two ortho/para directing groups which are meta to each other. This means you first have to add a meta-directing group, add the bromine and then convert the meta directing group. I mean to say that you start with benzene and react it with reagent i to get propanoylbenzene. Reagent a then will convert it to 3-bromo-1-propanoylbenzene. This has to be reduced using g.

Now the problem lies here. Since you have a benzylic alcohol you would want to use HBr to convert it to bromide but, I do not see any reagent listed. It might sound illogical but, there are only two things that you can try: h and j. J could oxidize the alcohol back to ketone. You might want to try h. I believe, there is no other way to achieve this transformation if you only have these listed reagents. The sequence is iagh. Sticking to these choices, it is the only probable reaction sequence, however I think this list is short on one reagent (HBr). Anyways, if you need to discuss anything, do not hesitate to post it in the comments box.

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