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Chapter 12: Problem 33

Draw the condensed structural formula for the alcohol formed when each of the following is reduced by hydrogen in the presence of a nickel catalyst: a. butyraldehyde b. acetone c. hexanal d. 2 -methyl- 3 -pentanone

Short Answer

Expert verified
a. Butanol - CH鈧僀H鈧侰H鈧侰H鈧侽H b. Isopropanol - CH鈧僀HOHCH鈧� c. Hexanol - CH鈧�(CH鈧�)鈧凜H鈧侽H d. 2-methyl-3-pentanol - CH鈧僀H鈧侰H(OH)CH(CH鈧�)鈧�

Step by step solution

01

- Understand the Reduction Process

Reduction of an aldehyde or ketone involves the addition of hydrogen (H鈧�) to the carbonyl group (C=O), converting it to an alcohol (R-OH) in the presence of a nickel catalyst.
02

- Identify the Reactants

Recognize the given compounds: a. Butyraldehyde: CH鈧僀H鈧侰H鈧侰HO b. Acetone: (CH鈧�)鈧侰O c. Hexanal: CH鈧�(CH鈧�)鈧凜HO d. 2-methyl-3-pentanone: CH鈧僀H鈧侰(O)CH(CH鈧�)鈧�
03

- Apply Reduction to Butyraldehyde

The reduction of butyraldehyde (CH鈧僀H鈧侰H鈧侰HO) results in butanol (CH鈧僀H鈧侰H鈧侰H鈧侽H).
04

- Apply Reduction to Acetone

The reduction of acetone, (CH鈧�)鈧侰O, results in isopropanol (CH鈧僀HOHCH鈧�).
05

- Apply Reduction to Hexanal

The reduction of hexanal (CH鈧�(CH鈧�)鈧凜HO) results in hexanol (CH鈧�(CH鈧�)鈧凜H鈧侽H).
06

- Apply Reduction to 2-methyl-3-pentanone

The reduction of 2-methyl-3-pentanone (CH鈧僀H鈧侰(O)CH(CH鈧�)鈧�) results in 2-methyl-3-pentanol (CH鈧僀H鈧侰H(OH)CH(CH鈧�)鈧�).

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Key Concepts

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

Aldehyde Reduction
Aldehyde reduction is a chemical reaction where an aldehyde (a compound with a terminal carbonyl group, -CHO) is converted into an alcohol (a compound with a -OH group). This process is achieved by adding hydrogen (H鈧�) to the carbonyl group (C=O).
In the presence of a catalyst such as nickel, the double bond between the carbon and oxygen in the aldehyde is broken, and hydrogen atoms are added to form an alcohol.
For example, butyraldehyde (CH鈧僀H鈧侰H鈧侰HO) is reduced to butanol (CH鈧僀H鈧侰H鈧侰H鈧侽H). The new -OH group replaces the =O in the aldehyde, forming a primary alcohol.
Ketone Reduction
Ketone reduction involves transforming a ketone (a compound with a carbonyl group located in the middle of the carbon chain, C=O) into an alcohol (specifically, a secondary alcohol) by adding hydrogen.
Similar to the reduction of aldehydes, the presence of a nickel catalyst facilitates this reaction.
During the reaction, hydrogen atoms add to the carbon and oxygen atoms of the carbonyl group, breaking the double bond and forming a hydroxyl group (OH) attached to a carbon atom.
For example, acetone ((CH鈧�)鈧侰O) is reduced to isopropanol (CH鈧僀HOHCH鈧�).
Alcohol Formation
Alcohol formation is the end goal of both aldehyde and ketone reductions. After hydrogenation, the carbonyl compounds turn into alcohols, characterized by the -OH group.
In aldehyde reductions, primary alcohols form, which means the -OH group is attached to a carbon atom that is also connected to only one other carbon.
In ketone reductions, secondary alcohols form, meaning the -OH group is attached to a carbon atom connected to two other carbon atoms.
Examples:
  • Butyraldehyde reduces to butanol (a primary alcohol).
  • Acetone reduces to isopropanol (a secondary alcohol).
Hydrogenation
Hydrogenation is a crucial process in organic chemistry where hydrogen atoms are added to other molecules.
In the context of reducing carbonyl compounds, hydrogenation involves adding hydrogen to the carbonyl groups (C=O) of both aldehydes and ketones to convert them into alcohols.
This process usually requires a catalyst to proceed efficiently and effectively.
Hydrogenation reduces the saturation level of a molecule, meaning double bonds break to allow these additional hydrogen atoms to attach, converting carbonyl groups to hydroxyl groups.
Nickel Catalyst
A nickel catalyst is a substance that speeds up the reduction process without being consumed in the reaction.
Nickel catalysts are commonly used in the hydrogenation of carbonyl compounds due to their ability to facilitate the addition of hydrogen molecules to carbonyl groups.
By using a nickel catalyst, the reduction of both aldehydes and ketones happens more efficiently at lower temperatures.
For example, in the reduction of hexanal (CH鈧�(CH鈧�)鈧凜HO) to hexanol (CH鈧�(CH鈧�)鈧凜H鈧侽H), the nickel catalyst helps in breaking the C=O bond and allows hydrogen atoms to bind, forming the -OH group.

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Most popular questions from this chapter

Which compound in each pair would be more soluble in water? Explain. a. pentane or 1 -propanol b. ethanol or ethyl methyl ether c. methanol or 1 -heptanol

Draw the condensed structural formula for each of the following: a. ethanol b. 3 -methyl- 2 -iodo- 1 -butanol c. 2 -propyn-1-ol (propargyl alcohol) d. 2 -fluorophenol

Draw the skeletal formula for each of the following: a. formaldehyde b. 2,3 -dichlorobutanal c. cyclohexanone d. acetone (propanone)

Draw the condensed structural or line-angle formula, if cyclic, for each of the following: (12.3) a. formaldehyde b. 2 -chlorobutanal c. 3 -methyl-2-hexanone d. 3,5 -dimethylhexanal

Compound \(X\) is 1 -hexanol. When compound \(X\) is heated with a strong acid, it dehydrates to form compound \(\mathbf{Y}\left(\mathrm{C}_{6} \mathrm{H}_{12}\right) .\) When compound \(\mathbf{X}\) is oxidized, compound \(\mathbf{Z}\left(\mathbf{C}_{6} \mathbf{H}_{12} \mathrm{O}\right)\) forms. Draw the condensed structural formulas and give the IUPAC names for compounds \(\mathbf{X}, \mathbf{Y},\) and \(\mathbf{Z}\)
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