Alcoholic Coordination

Chemistry Level 2

t-butyl ethanol \text{t-butyl ethanol} is mixed into a solution of heated sulfuric acid \text{sulfuric acid} and the major product is mixed with osmium tetroxide \text{osmium tetroxide} . The final product will contain one or more alcohol substituents. Your answer should be the sum of the carbon positions ( C O H C_{OH} ) an alcohol is attached. For example, if C 1 C_1 , C 3 C_3 , and C 9 C_9 all have alcohol groups, then your answer would be 1 + 3 + 9 = 13 1+3+9 = \boxed{13} . Use IUPAC numbering protocol when labeling the carbon positions in your answer.


David's Organic Chemistry Set

David's Physical Chemistry Set


The answer is 5.

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2 solutions

David Hontz
Jun 30, 2016

Notice the rearrangement to go from a 2 2^{\circ} carbocation to a more stable 3 3^{\circ} carbocation. Once the alkene is formed, osmium tetroxide will add alcohols to C 2 C_2 and C 3 C_3 ; thus Answer 2 + 3 = 5 \text{Answer} \Rightarrow 2+3= \boxed{5}

Did the same! :)

Prakhar Bindal - 4 years, 11 months ago

Heat is also required for the formation of C+ and double bond without heat π bond cannot be formed.

Archit Agrawal - 4 years, 11 months ago

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Yeah little heat will suffice As it is a 2 degree alcohol . in 3 degree heating is not required @David Hontz

Prakhar Bindal - 4 years, 11 months ago

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It is 2degree but with only 3 hyperconjugations which is same as primary but only have a little +I effect better than primary.

Archit Agrawal - 4 years, 11 months ago

Just one thing, though I got the answer right , it may be difficult for the others to get to know that the numbering is according to the IUPAC nomenclature.. so please mention it in the question

Vignesh S - 4 years, 11 months ago

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Excellent point. I've modified the question to mention IUPAC. Thank you for aiding in giving the question more clarity.

David Hontz - 4 years, 11 months ago

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No problem.. by the way, you have a nice collection of organic problems

Vignesh S - 4 years, 11 months ago
Aakhyat Singh
Feb 5, 2018

On dehydration of 3,3-dimethylbutan-2-ol, we will get 2,3-dimethylbut-2-ene(after carbocation rearrangement .i.e. methyl shift). On addition of OsO4 (syn addition of -OH) we get butan-2,3-diol

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