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Chapter 16: Problem 21

Why can't two molecules of acetone form a hydrogen bond with each other?

Short Answer

Expert verified
Acetone lacks hydrogens bonded to electronegative atoms, so it can't form hydrogen bonds with itself.

Step by step solution

01

Identifying Functional Groups in Acetone

Acetone, with the formula \( (CH_3)_2CO \), contains a carbonyl group (C=O). This group consists of a carbon atom double-bonded to an oxygen atom.
02

Understanding Hydrogen Bond Formation

Hydrogen bonding typically occurs between a hydrogen atom bonded to a highly electronegative atom (like N, O, or F) and another electronegative atom with a lone pair. This creates an attraction between the hydrogen and the other electronegative atom's lone pairs.
03

Evaluating Hydrogen Bond Donors in Acetone

In acetone, the oxygen in the carbonyl group is electronegative and has lone pairs, making it an acceptor, but there is no hydrogen directly bonded to an electronegative atom in acetone. Thus, there are no hydrogen atoms available to participate as donors in hydrogen bonding.
04

Analyzing Hydrogen Bond Acceptors in Acetone

While the oxygen in the carbonyl group can act as a hydrogen bond acceptor due to its lone pairs, hydrogen bonds require both a donor and an acceptor. Acetone lacks hydrogens bonded to electronegative atoms, so it cannot donate a hydrogen bond.
05

Drawing the Conclusion

Since acetone has no hydrogen atoms bonded to an electronegative atom, it can't form a hydrogen bond as a donor. Therefore, two acetone molecules can't hydrogen bond with each other.

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Key Concepts

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

Acetone Structure
Acetone is a simple organic compound commonly used as a solvent. Its formula is \( (CH_3)_2CO \), and it is the simplest ketone. The structure of acetone consists of three main parts:
  • Two methyl groups \((CH_3)\) bonded to a central carbon atom.
  • A carbonyl group \((C=O)\) at the center.
  • The central carbon atom is double-bonded to an oxygen atom.
The geometry of acetone is relatively simple. The molecule has a planar structure around the carbonyl carbon, which contributes to its reactivity. Understanding acetone's structure helps to see why it cannot form hydrogen bonds with itself.
Carbonyl Group
A carbonyl group is a significant functional group in organic chemistry, represented by \((C=O)\). It features a carbon atom double bonded to an oxygen atom. This group is highly influential in determining a molecule's properties due to its polarity.
In acetone, the carbonyl group is crucial because:
  • It contributes to the molecule's reactivity and ability to act as a hydrogen bond acceptor.
  • The oxygen atom in the carbonyl group is more electronegative than carbon, resulting in a polarized bond.
The carbonyl group's presence makes acetone an excellent solvent, but it also limits acetone's ability to form hydrogen bonds, as it serves only as an acceptor, not a donor.
Hydrogen Bond Donors
Hydrogen bonding is a type of attractive force, pivotal in many chemical and biological processes. For a molecule to act as a hydrogen bond donor, it must have a hydrogen attached to a highly electronegative atom, such as nitrogen, oxygen, or fluorine.
In acetone, the challenge arises because:
  • Acetone lacks a hydrogen atom attached to an electronegative atom.
  • Without a hydrogen donor, acetone cannot contribute a hydrogen to form a hydrogen bond.
This inability to donate a hydrogen atom to another electronegative atom is why acetone molecules cannot hydrogen bond with each other.
Electronegative Atoms
Electronegative atoms play a critical role in hydrogen bonding. They have a strong tendency to attract bonding electrons, which is why they are key components in hydrogen bonds.
Key points to understand about electronegativity in this context are:
  • Oxygen, nitrogen, and fluorine are considered highly electronegative atoms.
  • In acetone, the oxygen atom in the carbonyl group is electronegative, capable of attracting electrons strongly.
Even though the oxygen atom in acetone's carbonyl group can act as an acceptor due to its higher electronegativity, acetone lacks the hydrogen donors necessary to create hydrogen bonds. Therefore, despite having an electronegative atom, acetone can't complete a hydrogen bond with itself.

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Most popular questions from this chapter

Draw a structural formula for the product formed by treatment of butanal with each set of reagents. (a) \(\mathrm{H}_{2} /\) transition metal catalyst (b) \(\mathrm{NaBH}_{4},\) then \(\mathrm{H}_{2} \mathrm{O}\) (c) \(\quad \mathrm{Ag}\left(\mathrm{NH}_{3}\right)_{2}^{+}\) (Tollens' reagent) (d) \(\mathrm{K}_{2} \mathrm{Cr}_{2} \mathrm{O}_{2} / \mathrm{H}_{2} \mathrm{SO}_{4}\)

Answer true or false. (a) The reduction of an aldehyde always gives a primary alcohol. (b) The reduction of a ketone always gives a secondary alcohol. (c) The oxidation of an aldehyde gives a carboxylic acid. (d) The oxidation of a primary alcohol gives a ketone. (e) Tollens' reagent can be used to distinguish between an aldehyde and a ketone. (f) Sodium borohydride, \(\mathrm{NaBH}_{4}\), reduces an aldehyde to a primary alcohol. (g) The addition of one molecule of alcohol to the carbonyl group of a ketone gives a hemiacetal. (h) The reaction of an aldehyde with two molecules of alcohol gives an acetal, plus a molecule of water. (i) The formation of hemiacetals and acetals is reversible. (j) The cyclic hemiacetal formed from 4-hydroxypentanal has two stereocenters and can exist as a mixture of \(2^{2}=4\) stereoisomers.

Explain why the reduction of an aldehyde always gives a primary alcohol and the reduction of a ketone always gives a secondary alcohol.

Answer true or false. (a) An aldehyde is named as an alkanal, and a ketone is named as an alkanone. (b) The names for aldehydes and ketones are derived from the name of the longest carbon chain that contains the carbonyl group. (c) In an aromatic aldehyde, the carbonyl carbon is bonded to an aromatic ring.

Sodium borohydride is a laboratory reducing agent. NADH is a biological reducing agent. In what way is the chemistry by which each reduces aldehydes and ketones similar?
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