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Chapter 16: Problem 332

Derive an alcohol product from the following aldehyde precursors using any reagents and conditions necessary.

Short Answer

Expert verified
The alcohol product derived from an aldehyde precursor \( R-CHO \) can be obtained by performing a reduction reaction using Sodium Borohydride (NaBH4) as a reducing agent in a polar protic solvent under ice-cold conditions, followed by protonation of the resulting alkoxide ion intermediate with an acid. The final alcohol product is \( R-CH(OH) \), where "R" represents any alkyl or aryl group, and "CH(OH)" represents an alcohol functional group.

Step by step solution

01

Write down the given aldehyde precursor

First, let's write down the aldehyde precursor whose structure is: \( R-CHO \) Where "R" represents any alkyl or aryl group, and "CHO" represents an aldehyde functional group.
02

Identify the reducing agent and conditions

We'll use Sodium Borohydride (NaBH4) as the reducing agent in this reduction reaction. The conditions for this reaction are a polar protic solvent, such as ethanol or methanol, and ice-cold temperatures.
03

Perform the reduction reaction

Next, we'll perform the reduction reaction by treating the aldehyde precursor with the reducing agent (NaBH4) in the polar protic solvent under ice-cold conditions. The general reaction scheme can be written as: \( R-CHO + NaBH_4 \rightarrow R-CH(O^-)Na + BH_3 \) In this step, the reducing agent (NaBH4) donates a hydride ion (H-) to the carbonyl carbon of the aldehyde, leading to the formation of an alkoxide ion intermediate (R-CH(O-)). At the same time, sodium ions (Na+) and borane (BH3) are generated as byproducts.
04

Protonate the alkoxide ion intermediate

The last step of the reaction is to protonate the alkoxide ion intermediate (R-CH(O-)) in order to form an alcohol product. This can be achieved using an acid, such as water or dilute hydrochloric acid (HCl), as a proton source: \( R-CH(O^-) + H_3O^+ \rightarrow R-CH(OH) + H_2O \) Here, the alkoxide ion receives a proton (H+) from the acid, resulting in the formation of an alcohol product (R-CH(OH)) and water as the byproduct.
05

Write down the final alcohol product

After completing the reduction reaction and protonation steps, we have derived an alcohol product from the given aldehyde precursor. The final alcohol product is: \( R-CH(OH) \) where "R" represents any alkyl or aryl group, and "CH(OH)" represents an alcohol functional group. In conclusion, we have successfully derived an alcohol product from the aldehyde precursor by performing a reduction reaction using Sodium Borohydride (NaBH4) as a reducing agent and then protonating the resulting alkoxide ion with an acid.

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Most popular questions from this chapter

Predict the products of hydroboration-oxidation of: (a) cis-2-phenyl-2-butene; (b) trans \(-2\) -phenyl-2-butene; (c) 1 -methylcyclohexene.

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