DAT Achiever test #5, ochem#90 HELP!

[N8D9]

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Hi guys

I don't know how many of you have the 5th test of the DAT achiever but I had a question regarding #90 (Ochem) - I understand the solution, but I wanted to know why option "E" is wrong? wouldn't the addition of D2O break the alkene and attach to the more substituted Carbon as well (as shown in E)

For those who don't have this test, the question consists of a Benzene ring to which -CH=CH-COCl is attached at position 1 and -OH is attached at position 3. This molecule is then reacted with D2O(l) to produce what?

Please help me clarify this..

THANK YOU!

 

[LaughingGas]

Hi guys

I don't know how many of you have the 5th test of the DAT achiever but I had a question regarding #90 (Ochem) - I understand the solution, but I wanted to know why option "E" is wrong? wouldn't the addition of D2O break the alkene and attach to the more substituted Carbon as well (as shown in E)

For those who don't have this test, the question consists of a Benzene ring to which -CH=CH-COCl is attached at position 1 and -OH is attached at position 3. This molecule is then reacted with D2O(l) to produce what?

Please help me clarify this..

THANK YOU!

If i remember correctly addition of water (this case D2O instead of H2O) you need acid catalyst. D2O itselt has a poor acidic D and D-O bonds are strong. Using D2O solely there is no reaction because the D+ is not a strong electrophile to break alkene double bond.

 

[bharat008]

Hi guys

I don't know how many of you have the 5th test of the DAT achiever but I had a question regarding #90 (Ochem) - I understand the solution, but I wanted to know why option "E" is wrong? wouldn't the addition of D2O break the alkene and attach to the more substituted Carbon as well (as shown in E)

For those who don't have this test, the question consists of a Benzene ring to which -CH=CH-COCl is attached at position 1 and -OH is attached at position 3. This molecule is then reacted with D2O(l) to produce what?

Please help me clarify this..

THANK YOU!

I would have guessed the answer to be substitution of CHLORIDE group with OD. Cl is a good leaving group and highly reactive and it would be replaced by OD... Hope that helps.

You can't break the alkene in the absence of ACID... D20 would have to be Acid Catalyzed to break the alkene..

 

[N8D9]

Hey thanks guys, I do, now, recall that acid should be necessary 🙂

Also, the COCl does become COOD and the OH becomes OD.

Thanks again, and good luck!!