Practice Exam Question: - Consider the formation of a Grignard reagent from an a

Question

Practice Exam Question:

- Consider the formation of a Grignard reagent from an alkyl halide, as shown below:

CH3CH2CH2Br + Mg CH3CH2CH2MgBr

Determine the starting and ending oxidation states of the bolded carbon. Is that carbon oxidized or reduced?

- The reaction performed (Oxidation of Cyclooctanol to Cyclooctanone) is limited to secondary alcohols since primary alcohols will often overoxidize to the carboxylic acid. Explain why the reaction will not work on tertiary alcohols either.

- In many cases, charges and oxidation numbers are similar, if not the same –this is the case for the atoms in MgCl2. That said, for organic molecules,charges and oxidation numbers can be and usually are very different. Explain why atom/ion charges and oxidation number are essentially the same for MgCl2 while they are very different for something like methane,and the assumptions that are made when discussing each. Be sure to support your claims!

Explanation / Answer

CH3CH2CH2Br + Mg CH3CH2CH2MgBr

- The starting and ending oxidation states of the bolded carbon are -1 and -3 respectively. The carbon is reduced.

- Tertiary alcohols are not easily oxidised because, unlike primary and secondary alcohols, they do not have a hydrogen atom attached to the same carbon atom as the hydroxyl group

- In organic molecules like methane or ethane

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