Question

In: Chemistry

My compound is 2,4-Dimethyl-1-Pentanol 1.       Retrosynthetic analysis of your compound: What is a possible precursor?   What...

My compound is 2,4-Dimethyl-1-Pentanol

1.       Retrosynthetic analysis of your compound: What is a possible precursor?   What are the reagents you need to obtain your product when using this precursor?     

2.       In a drawing, show the synthetic steps that lead from the precursor to your compound. Use curved arrows properly!

3.       Using your precursor, show mechanisms and products of a Markovnikov and an anti-Markovnikov addition.

4.       Using the materials obtained through Markovnikov and anti-Markovnikov additions to the precursor, discuss stereochemical aspects. That means: Enantiomers? Diastereomers? Regioisomers? E. g., Markovnikov addition yields the (?)-enantiomer, while …   . Are the compounds chiral or achiral, why is that?

          Indicate the proper orientation of substituents by drawing structures with wedges and dashes where necessary.

5.         Identify all chiral centers in your substance and assign R- or S- designations.        

Solutions

Expert Solution

1. Given below is a retrosynthetic analysis for 2,4-dimethyl-2-pentanol

2. Shown below is a complete synthetic scheme for the formation of the compound from its precursor.

3. Given below the Markovnikov's addition which forms the most substituted alcohol product and the anti-Markovnikov's additon forming the desired alcohol product mechanisms

4. The compounds formed by Markovnikov's and anti-Markovnikov's rule of addition would be consitutional isomers or regioisomers. The compounds formed would be achiral. In both the saces the addition can be from either side giving us mixture of enantiomers in each case.

5. Shown below are possible products formed provided the other centers are also chiral.


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