Chapter 4: Problem 25
1-Propanol can be prepared from propene by (a) \(\mathrm{HOH} / \mathrm{H}^{\oplus}\) (b) \(\mathrm{Hg}(\mathrm{OAc})_{2} / \mathrm{H}_{2} \mathrm{O}\) and \(\mathrm{NaBH}_{4}\) (c) \(\mathrm{B}_{2} \mathrm{H}_{6}-\mathrm{THF}\) and \(\mathrm{H}_{2} \mathrm{O}_{2} / \mathrm{OH}^{-}\) (d) All of these
Short Answer
Step by step solution
Understand the question
Evaluate mechanism (a)
Evaluate mechanism (b)
Evaluate mechanism (c)
Conclusion
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Alkenes
One key feature of alkenes is their unsaturation, meaning they can undergo addition reactions, where new atoms are added to the carbons of the double bond, converting it into a single bond.
In the context of the exercise, propene, which contains a three-carbon chain with one double bond, acts as the starting alkene. Due to the reactivity of its double bond, propene can be transformed into 1-propanol using the hydroboration-oxidation reaction.
Alcohols
Depending on the carbon to which the hydroxyl group is attached, alcohols are classified as primary, secondary, or tertiary:
- Primary Alcohols: The hydroxyl group is attached to a carbon atom bonded to only one other carbon.
- Secondary Alcohols: The hydroxyl group is bonded to a carbon atom attached to two other carbons.
- Tertiary Alcohols: The hydroxyl group is connected to a carbon atom that is linked to three other carbons.
In the exercise, 1-propanol, produced from propene, is a primary alcohol because the -OH group is attached to a terminal carbon atom.
Hydroboration-Oxidation
This is followed by the oxidation step, where the boron atom is replaced by a hydroxyl group using hydrogen peroxide (_2O_2) in a base (such as ^-). This reaction sequence is noteworthy as it yields primary alcohols from terminal alkenes, due to the unique orientation of addition, contrary to most hydration reactions.
Therefore, this method is optimal for converting propene into 1-propanol, as detailed in the solution.
Markovnikov and anti-Markovnikov addition
In contrast, anti-Markovnikov addition is the opposite of this rule. In such reactions, the substituent that isn't hydrogen (such as a hydroxyl group) attaches to the less substituted carbon.
Hydroboration-oxidation is a classic example of an anti-Markovnikov reaction because it results in primary alcohols when applied to simple alkenes. This deviation from Markovnikov's rule allows chemists to selectively synthesize alcohols with specific structures, as seen in the transformation of propene to 1-propanol without forming more complex branching.