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Chapter 15: Problem 22

Using your old and new roadmaps as a guide, show how to convert 1-bromo-3methylbutane into 2,7-dimethyloctane. You must use 1-bromo-3-methylbutane as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way. CC(C)CCBr CC(C)CCCCC(C)C 1-Bromo-3-methylbutane 2,7-Dimethyloctane

Short Answer

Expert verified
Question: Describe the synthesis process to convert 1-bromo-3-methylbutane into 2,7-dimethyloctane. Answer: The synthesis process involves four main steps: 1. Formation of a Grignard reagent (3-methylbutylmagnesium bromide) by reacting 1-bromo-3-methylbutane with magnesium metal in anhydrous ether. 2. Preparation of a suitable ketone, in this case, 3-pentanone. 3. Reaction of the Grignard reagent with the ketone to form a tertiary alcohol, 2,7-dimethyloctan-2-ol. 4. Dehydration of the tertiary alcohol using a dehydrating agent like concentrated sulfuric acid to obtain the final product, 2,7-dimethyloctane.

Step by step solution

01

Formation of a Grignard reagent

Start by converting the 1-bromo-3-methylbutane into a Grignard reagent by reacting it with magnesium metal in the presence of anhydrous ether. This will result in the formation of a 3-methylbutylmagnesium bromide Grignard reagent. Reaction: 1-bromo-3-methylbutane + Mg → 3-methylbutylMgBr
02

Preparation of a ketone

Next, prepare a suitable ketone for the Grignard reagent to react with. In this case, we need 3-pentanone. Reaction: H_3CCH_2COCH_2CH_3 (3-pentanone)
03

Grignard reaction with the ketone

Now react the 3-methylbutylmagnesium bromide Grignard reagent prepared in step 1 with 3-pentanone prepared in step 2 to form a tertiary alcohol. Reaction: 3-methylbutylMgBr + 3-pentanone → 2,7-dimethyloctan-2-ol
04

Dehydration of tertiary alcohol

Finally, we need to convert the resultant 2,7-dimethyloctan-2-ol into 2,7-dimethyloctane. This can be done by dehydrating the tertiary alcohol using an appropriate dehydrating agent like concentrated sulfuric acid. Reaction: 2,7-dimethyloctan-2-ol → 2,7-dimethyloctane + H_2O Following these steps, we have successfully converted 1-bromo-3-methylbutane into 2,7-dimethyloctane using various reagents and reactions.

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Most popular questions from this chapter

Show how spiro[2.2]pentane can be prepared in one step from organic compounds containing three carbons or less and any necessary inorganic reagents or solvents. Spiro [2.2] pentane

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