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Chapter 11: Problem 43

Give the structural formula and systematic name for the product, if any, from the reactions of each of the following pairs of compounds: (a) pentanal and \(\mathrm{KMnO}_{4}\) (b) pentanal and \(\mathrm{LiAlH}_{4}\) (c) 2-octanone and \(\mathrm{LiAlH}_{4}\) (d) 2 -octanone and \(\mathrm{KMnO}_{4}\)

Short Answer

Expert verified
(a) Pentanoic acid, (b) 1-pentanol, (c) 2-octanol, (d) 2-octanone (no change).

Step by step solution

01

Understanding the Reactions

We are dealing with pairs of compounds reacting with either \(\text{KMnO}_4\) or \(\text{LiAlH}_4\). We'll address the chemical changes step by step.
02

Reaction (a) Pentanal with KMnO4

\( \text{KMnO}_4 \) is a strong oxidizing agent. When reacted with pentanal, it oxidizes the aldehyde to a carboxylic acid, forming pentanoic acid. The structural formula is \( \text{CH}_3(\text{CH}_2)_3\text{COOH} \).
03

Naming the Product (a)

The systematic name of the product is pentanoic acid.
04

Reaction (b) Pentanal with LiAlH4

\( \text{LiAlH}_4 \) is a strong reducing agent. When reacted with pentanal, it reduces the aldehyde to a primary alcohol, forming 1-pentanol. The structural formula is \( \text{CH}_3(\text{CH}_2)_3\text{CH}_2\text{OH} \).
05

Naming the Product (b)

The systematic name of the product is 1-pentanol.
06

Reaction (c) 2-Octanone with LiAlH4

\( \text{LiAlH}_4 \) reduces the ketone group to an alcohol. For 2-octanone, it forms 2-octanol. The structural formula is \( \text{CH}_3(\text{CH}_2)_4\text{CHOHCH}_3 \).
07

Naming the Product (c)

The systematic name of the product is 2-octanol.
08

Reaction (d) 2-Octanone with KMnO4

\( \text{KMnO}_4 \) usually oxidizes primary and secondary alcohols. Since 2-octanone is already oxidized, it remains unchanged by \( \text{KMnO}_4 \).
09

Naming the Product (d)

There is no change, so the name remains 2-octanone.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Aldehyde Oxidation
Aldehydes are organic compounds characterized by the presence of a carbonyl group bonded to at least one hydrogen atom. When an aldehyde is exposed to a strong oxidizing agent like potassium permanganate (\(\mathrm{KMnO}_4\)), it undergoes an oxidation reaction.
In this reaction, the aldehyde group is converted into a carboxylic acid.
  • The carbonyl carbon gains an additional oxygen, leading to a new hydroxyl group, transforming the compound into a carboxylic acid.
  • For example, when pentanal oxidizes, it turns into pentanoic acid with the structural formula \(\text{CH}_3(\text{CH}_2)_3\text{COOH}\)
This process is fundamental in organic chemistry because it transforms molecules into more reactive species or prepares them for further reactions.
Ketone Reduction
Ketones are a type of organic compound that feature a carbonyl group bonded to two carbon atoms. Unlike aldehydes, ketones cannot be oxidized to carboxylic acids under normal conditions but can be reduced to alcohols.
When a ketone reacts with a strong reducing agent like lithium aluminum hydride (\(\mathrm{LiAlH}_4\)), it undergoes a reduction process.
  • This reaction converts the carbonyl group into a hydroxyl group, resulting in an alcohol.
  • For example, the reduction of 2-octanone produces 2-octanol, with the structural formula \(\text{CH}_3(\text{CH}_2)_4\text{CHOHCH}_3\)
This type of reaction is useful because it transforms functional groups into others, allowing for the synthesis of complex molecules from simpler precursors.
Organic Reactions
Organic reactions involve the making and breaking of chemical bonds within organic molecules. They are essential to chemistry because they form the basis for creating nearly all organic compounds.
Key reactions include oxidation and reduction, where the functional groups of organic compounds are transformed.
  • Oxidation typically involves increasing the oxygen content or removing hydrogen.
  • Reduction involves increasing hydrogen content or removing oxygen.
These reactions enable chemists to modify molecules to enhance their properties or combine them to create new substances. In educational settings, understanding these reactions helps students grasp the complex processes involved in organic chemistry.
Systematic Nomenclature
Systematic nomenclature in chemistry refers to a set of rules used to generate a standard name for chemical compounds.
It allows chemists to precisely describe a molecule's composition and structure.
  • For carbon compounds, this often involves identifying the length of the carbon chain and the type and position of functional groups.
  • For example, in 'pentanoic acid', 'pent' indicates five carbons, and 'oic acid' signals a carboxylic acid group.
  • Similarly, '1-pentanol' signifies a primary alcohol derived from pentane.
This system is crucial because it ensures consistent communication among chemists worldwide, reducing misunderstandings and improving clarity in scientific discourse.

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Most popular questions from this chapter

Write an equation for the formation of the following polymers. (a) polystyrene, from styrene \(\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}=\mathrm{CH}_{2}\right)\) (b) PET (polyethylene terephthalate), from ethylene glycol and terephthalic acid

Structural Isomers (a) Draw all of the isomers possible for \(\mathrm{C}_{3} \mathrm{H}_{8} \mathrm{O}\). Give the systematic name of each and tell into which class of compounds it fits. (b) Draw the structural formula for an aldehyde and a ketone with the molecular formula \(\mathrm{C}_{4} \mathrm{H}_{8} \mathrm{O}\). Give the systematic name of each.

Elemental analysis of a colorless liquid has given its formula as \(\mathrm{C}_{5} \mathrm{H}_{10}\). You recognize that this compound could be either a cycloalkane or an alkene. A chemical test to determine the class to which it belongs involves adding bromine. Explain how this reaction would allow you to distinguish between the two classes.

What is the molecular formula for an alkane with 12 carbon atoms?

Addition of water to alkene \(\mathbf{X}\) gives an alcohol \(\mathbf{Y}\). Oxidation of \(\mathbf{Y}\) produces 3,3 -dimethyl-2-pentanone. Identify \(\mathbf{X}\) and \(\mathbf{Y}\), and write equations for the two reactions.
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