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Retrosynthetic Analyses Involving Alkylation of an Alkynide Ion

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Questions on Retrosynthetic analyses involving alkylation of an alkynide ion.
Please help me with attached problems 2, 3, and 4. Thanks very much! :)

Please help me with problems 2, 3, and 4. Aren't there certain rules you have to follow for alkylation, such as (1) you can't be branched at carbon 2 and (2) you have to end up with a primary alkyl halide

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Solution Summary

The retrosynthetic analyses involving alkylation of an alkynide ion is examined.The solution offers a guide to solving the questions with the aid of clear diagrams and description of steps.

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The following word document includes the solutions to questions 2,3,and 4.

Since we are looking for a compound that was formed by alkylating by an alkynide ion we can directly say it was produced by a C C-
Which means that the bond must have been formed through some of the alkyl chains in the middle of the compound

The arrows indicate the only possible places in which you can actually have an alkynide ion previously used. This reaction in general would be made using an alkyl halide with a chain that contais a triple bond at the end
The general formula would be:

RBr ...

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