Wittig rxn help

[Wererew]

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Could anyone clarify this for me?

I do not understand how the phosphorus jumped and the carbon chain changed,

I thought that CH3Li would take off the hydrogen of middle carbon to make an ylide

(This is from solution of orgo odyssey ch13)

 

[Artdent97]

This is in solution mannual

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[Wererew]

This is in solution mannual

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This is the solution... I am confused about the first step

 

[Wererew]

Bump! Sorry I am still very confused, but haven't seen much people use the orgo odyssey 🙁 @orgoman22

 

[dentsurg22]

Could anyone clarify this for me?

I do not understand how the phosphorus jumped and the carbon chain changed,

I thought that CH3Li would take off the hydrogen of middle carbon to make an ylide

(This is from solution of orgo odyssey ch13)

Where exactly did the Chloride in LiCl come from? Seems like a mistake to me

 

[Wererew]

Where exactly did the Chloride in LiCl come from? Seems like a mistake to me

That's exactly how it is written in the solution manual and i cannot figure out what I am missing (if it is a difficult/trick question).. I was thinking that it might not be a mistake so I just wanted to learn/ get some clarification

 

[Steeezy]

This looks like a mistake, no big deal. You are correct in that the purpose of the CH3- is to deprotonate the carbon bonded to the phosphorus in order to create the ylide. I'd be surprised if there was any other answer here. See attached pic.

 

[Wererew]

that problem has been corrected See attachment.

Dr. RomanoView attachment 221762

Thank you Dr. Romano but is there supposed to be a negative charge on the Carbon instead of the Phosphorus?

 

[DAT Destroyer]

Bump! Sorry I am still very confused, but haven't seen much people use the orgo odyssey 🙁 @orgoman22

Sorry for all the confusion, this should clear it up.

The solution to #54 is correct, in this Wittig. A cycloalkene with an exocyclic double bond is shown in choice C. The typo was recently corrected. The by product is Lithium iodide, not LiCl. The ylide also has a C...it should be a P. We have thousands of problems in this book, the occasional error creeps in. Thanks for the great catch.

Hope this helps.

Dr. Romano

 

[Wererew]

Sorry for all the confusion, this should clear it up.

The solution to #54 is correct, in this Wittig. A cycloalkene with an exocyclic double bond is shown in choice C. The typo was recently corrected. The by product is Lithium iodide, not LiCl. The ylide also has a C...it should be a P. We have thousands of problems in this book, the occasional error creeps in. Thanks for the great catch.

Hope this helps.

Dr. Romano

Yes I am enjoying the book, I love how it is organized by topic so I can focus one at a time!

Thank you for the clarification