2011 DAT Destroyer #107 OCHEM

[pandalove89]

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So the reaction first starts off with a cyclohexene.

1. H30+ is added so an OH and H group gets added on to the double bond.

2. Oxidizing agent makes OH into a ketone

3. then CH3Li, Et2O with H3O+ is added. I don't understand this last step. What is this exactly??

 

[needzmoar]

So the reaction first starts off with a cyclohexene.

1. H30+ is added so an OH and H group gets added on to the double bond.

2. Oxidizing agent makes OH into a ketone

3. then CH3Li, Et2O with H3O+ is added. I don't understand this last step. What is this exactly??

it's similar to the grignard reagent

 

[PooyaH]

it's similar to the grignard reagent

Indeed!

 

[indigenoustw]

CH3Li is an organometallic compound just like CH3MgBr. So CH3Li will attack the carbonyl carbon and result the addition of a methyl group. After acidic workup, forms 1-methylcyclohexanol.

 

[rmm30]

it's similar to the grignard reagent

RLi is organolithium. As others have said it reacts the same way as grignard ie it's an excellent carbon nucleophile.