Show the entire multistep reaction scheme from butyl alcohol to final product.

Macroscale and Microscale Organic Experiments
7th Edition
ISBN:9781305577190
Author:Kenneth L. Williamson, Katherine M. Masters
Publisher:Kenneth L. Williamson, Katherine M. Masters
Chapter7: Extraction
Section: Chapter Questions
Problem 7Q
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Please answer the question at the bottom, Thanks.

LAB NOTES FOR PREPARATION OF BUTYL MAGNESIUM BROMIDE
AND ITS SUBSEQUENT CONVERSION TO AN ALCOHOL

To the reaction flask were added 2.5967 gram of magnesium turnings, about 20 ml
of diglyme, and a solution of 13.5942 gram of butyl bromide in about 25 ml
diglyme.
The procedure as per the lab manual was initiated. After the required heating time
was completed the reaction mixture was allowed to cool to room temperature.
Then a solution of 6.1123 gram of acetone in about 15 ml of diglyme was added
dropwise as per the lab manual.
The rest of the lab manual procedure was completed, ultimately affording 2.5532
gram of an oily, clear and slightly yellow liquid, presumed to be 2-methyl-2-
hexanol. Boiling point as measured by distillation was 138 – 141 deg C.
About 0.8 ml of the presumed 2-methyl-2-hexanol was placed in an NMR tube to
which was added 2 drops of TMS. The tube was capped, then inverted and righted
20 times to thoroughly mix the product and TMS.
Subsequently, Proton, Carbon – 13 and DEPT NMR spectra were acquired at the
Cumberland Campus using the Anasazi 60MHz FT NMR spectrometer.
The IR spectrometer was unavailable.

Show the entire multistep reaction scheme from butyl alcohol to final product.

Expert Solution
Step 1

The alkyl magnesium bromide popularly known as the Grignard reagent can be used as reagent for various organic synthesis. It is an organometallic compound formed from reacting alkyl bromides with Mg metal in presence of ether. In presence of carbonyl group, the reagent undergoes nucleophilic addition to form alcohols.

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