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Chapter 10: Problem 52

Give the structural formula and name for the organic product from the following reactions. (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CHO}+\mathrm{LiAlH}_{4}\) (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}+\mathrm{KMnO}_{4}\)

Short Answer

Expert verified
(a) 1-Butanol (CH鈧僀H鈧侰H鈧侰H鈧侽H). (b) Butanoic acid (CH鈧僀H鈧侰H鈧侰OOH).

Step by step solution

01

Understand the Reagents and Initial Compounds (Reaction a)

The initial compound is butanal (CH鈧僀H鈧侰H鈧侰HO), an aldehyde. The reagent is LiAlH鈧� (lithium aluminum hydride), a strong reducing agent.
02

Determine the Reduction Product (Reaction a)

LiAlH鈧� reduces aldehydes to primary alcohols. Therefore, butanal will be reduced to butanol, specifically 1-butanol or n-butanol.
03

Draw the Structural Formula (Reaction a)

The structural formula for 1-butanol is CH鈧僀H鈧侰H鈧侰H鈧侽H. The aldehyde group is replaced by a hydroxyl group when reduced by LiAlH鈧�.
04

Understand the Reagents and Initial Compounds (Reaction b)

The initial compound is 1-butanol (CH鈧僀H鈧侰H鈧侰H鈧侽H), a primary alcohol. The reagent is KMnO鈧�, a strong oxidizing agent often used in acidic or basic solutions.
05

Determine the Oxidation Product (Reaction b)

KMnO鈧� will oxidize the primary alcohol to a carboxylic acid. Therefore, 1-butanol will be oxidized to butanoic acid.
06

Draw the Structural Formula (Reaction b)

The structural formula for butanoic acid is CH鈧僀H鈧侰H鈧侰OOH. The primary alcohol group is oxidized to a carboxylic acid group.

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Key Concepts

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

Aldehydes to Alcohols Reduction
Reducing aldehydes to alcohols is a common reaction in organic chemistry that involves the addition of hydrogen to a carbonyl group. A popular reagent for this transformation is Lithium aluminum hydride (LiAlH鈧�), which is a very strong reducing agent.
When an aldehyde like butanal (CH鈧僀H鈧侰H鈧侰HO) is treated with LiAlH鈧�, the aldehyde's carbonyl group (C=O) undergoes reduction. This process converts the double-bonded oxygen into a hydroxyl group (OH), turning the aldehyde into a primary alcohol like 1-butanol (CH鈧僀H鈧侰H鈧侰H鈧侽H).
Here's how it works:
  • The aldehyde molecule interacts with LiAlH鈧�, which donates hydride ions (H鈦�).
  • A hydride ion attacks the carbonyl carbon, breaking the double bond and forming a new bond with the oxygen.
  • This results in an alcohol, as the oxygen in the original carbonyl group now holds an extra hydrogen, becoming an OH group.
Understanding this reduction reaction is crucial because it often serves as a step in the synthesis of more complex organic compounds.
Oxidation of Alcohols
The oxidation of alcohols is another fundamental reaction in organic chemistry. It involves increasing the oxidation state of the alcohol's carbon, typically converting it into a carbonyl compound.
A common oxidizing agent used for primary alcohols like 1-butanol (CH鈧僀H鈧侰H鈧侰H鈧侽H) is potassium permanganate (KMnO鈧�). KMnO鈧� will oxidize 1-butanol to butanoic acid (CH鈧僀H鈧侰H鈧侰OOH), a primary alcohol to a carboxylic acid conversion.
  • Initially, the primary alcohol's hydroxyl group undergoes oxidation, increasing the oxidation state.
  • The oxidation converts the alcohol group into a carboxylic acid group by formulating a C=O (carbonyl) group and an OH (hydroxyl) group attached to the same carbon, forming the COOH structure.
  • This oxidation reaction is essential in organic synthesis, as it helps create carboxylic acids, which are vital building blocks in numerous chemical processes.
Recognizing the role of oxidation in transforming alcohols into acids provides insights into the broader scope of chemical reactions and pathways.
Structural Formulas
Structural formulas are crucial representations in organic chemistry that depict the arrangement of atoms within a molecule. They help chemists visualize and understand how atoms are connected, which in turn influences the properties and reactions of the molecules.
For instance, taking the molecule 1-butanol with the structural formula CH鈧僀H鈧侰H鈧侰H鈧侽H, shows:
  • Four carbon atoms in a straight chain, illustrating its primary alcohol structure.
  • Attached to the terminal carbon is a hydroxyl group (OH), signifying its alcohol functional group.
When considering the oxidation product butanoic acid, with the formula CH鈧僀H鈧侰H鈧侰OOH:
  • The same linear chain of carbon atoms is seen, as in 1-butanol.
  • However, the oxidation converts the terminal alcohol group into a carboxylic acid group (COOH).
  • This subtle yet significant change is easily visualized through the structural formula, highlighting the impact of chemical reactions on molecular structure.
Structural formulas thus serve as a visual map for chemists, detailing important aspects of molecular architecture that might not be immediately apparent from a molecule's empirical or molecular formula alone.

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Most popular questions from this chapter

An unknown colorless liquid has the formula \(\mathrm{C}_{4} \mathrm{H}_{10} \mathrm{O}\) Draw the structures for the four alcohol compounds that have this formula.

Draw the structure of 2 -butanol. Identify the chiral carbon atom in this compound. Draw the mirror image of the structure you first drew. Are the two molecules superimposable?

Write equations for the following reactions, representing the reactants and products using structural formulas. (a) The hydrolysis of the amide \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CONHCH}_{3}\) to form benzoic acid and methylamine (b) The hydrolysis of \(+\mathrm{CO}\left(\mathrm{CH}_{2}\right)_{4} \mathrm{CONH}\left(\mathrm{CH}_{2}\right)_{6} \mathrm{NH} \rightarrow_{n}\) (nylon-6,6, a polyamide) to give a carboxylic acid and an amine

Give the structural formula and systematic name for the organic product, if any, from each of the following reactions: (a) pentanal and \(\mathrm{KMnO}_{4}\) (b) 2 -octanone and \(\operatorname{LiAl} \mathbf{H}_{4}\)

Draw Lewis structures and name three structural isomers with the formula \(\mathrm{C}_{6} \mathrm{H}_{12} .\) Are any of these isomers chiral?
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