Organic Chemistry : Organic Concepts

Study concepts, example questions & explanations for Organic Chemistry

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Example Questions

Example Question #1 : Intermolecular Forces And Stability

Which of the following molecules has the lowest boiling point?

Possible Answers:

2-methylpentane

Hexane

2,3-dimethylbutane

Pentane

Correct answer:

2,3-dimethylbutane

Explanation:

When discussing boiling points of hydrocarbons, it is important to remember that branching decreases a molecule's boiling point. We can first eliminate hexane and pentane as our answers, as neither are branched. From here, we can come upon 2,3-dimethylbutane as our answer because it is more branched than 2-methylpentane. Also important when ranking hydrocarbons in terms of boiling point is the number of carbons - more carbons means a higher boiling point.

Example Question #231 : Organic Concepts

Rank the given molecules in order of increasing boiling point.

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Possible Answers:

II, III, I, IV, V

II, V, IV, I, III

V, IV, I, III, II

I, IV, III, V, II

IV, V, I, III, II

Correct answer:

V, IV, I, III, II

Explanation:

Most polar (II) has highest boiling point due to hydrogen bonds. The other molecules: increasing boiling point with decreased branching of the molecule (the more branched, the less surface area, and the lower the boiling point due to molecular stacking).

Example Question #11 : Intermolecular Forces And Stability

Which of the following intermolecular forces is the strongest?

Possible Answers:

London dispersion forces

Ion-dipole interactions

Hydrogen bonding

All of these have approximately the same strength

Dipole-dipole interactions

Correct answer:

Hydrogen bonding

Explanation:

The strongest of those listed s hydrogen bonding. This type of intermolecular force is the attraction that occurs between hydrogen atoms and the lone pairs on atoms of oxygen, nitrogen and/or fluorine. Hydrogen bonds are the strongest while dispersion forces are the weakest. The strength of hydrogen bonds is responsible for properties of water such as high specific heat capacity, high surface tension, cohesion, high boiling point, and other.

Example Question #12 : Help With Intermolecular Forces

A researcher is trying to identify a molecule. He observes that there is a weak hydrophobic bond between adjacent molecules. He also notices a weak polar interaction between the molecules. Which of the following could be the identity of the molecule?

Possible Answers:

Hexane

More than one of the above could be the identity of this molecule

Hydrochloric acid

Hydrobromic acid

Correct answer:

More than one of the above could be the identity of this molecule

Explanation:

Intermolecular bonds occur between adjacent molecules (recall that ‘inter’ means ‘between’). There are several types of intermolecular bonds. Hydrophobic bonds, or van der Waals forces, are the weakest intermolecular forces and occur between every molecule; therefore, all of the listed molecules in the question have hydrophobic bonds. Polar interactions between molecules occur between charged species or polar molecules. Recall that polar molecules are molecules that contain two or more atoms with very different electronegativities. The more electronegative atom pulls the electrons closer to itself, causing polarity in the molecule. The more electronegative atom will have a partial negative charge (due to the proximity to electrons) and the less electronegative atom will have a partial positive charge. This polarity in molecule allows for dipole-dipole interactions, a type of intermolecular force.

To solve this question, we need to determine which molecules are polar. Hexane, or , has only carbon and hydrogen atoms. Carbon and hydrogen electronegativities are very similar; therefore, this molecule is nonpolar. Hydrofluoric acid () have two atoms with very different electronegativities; therefore, this molecule is polar and will have polar interactions. Similarly, hydrobromic acid () will also be polar and will have polar interactions.

Example Question #11 : Intermolecular Forces And Stability

Which of the following is considered the strongest intermolecular bond?

Possible Answers:

Dipole-dipole interactions

Hydrogen bond

Ionic bond

Covalent bond

Correct answer:

Hydrogen bond

Explanation:

Intermolecular bonds occur between adjacent molecules whereas intramolecular bonds occur within molecules. Examples of intermolecular bonds include hydrogen bonds, van der Waals interactions, and dipole-dipole interactions. The strongest intermolecular bond is hydrogen bond whereas the weakest is the van der Waals interactions. Covalent bonds and ionic bonds occur within molecules and are termed intramolecular bonds. Covalent bond is the strongest intramolecular bond.

Example Question #11 : Help With Intermolecular Forces

Which type of intermolecular force explains why butanal has a lower boiling point than octanal?

Possible Answers:

Covalent bonding

Dipole-dipole interactions

van der Waals interactions

Ion-dipole interactions

Hydrogen bonding

Correct answer:

van der Waals interactions

Explanation:

As a molecule's mass increases, van der Waal forces also increases due to an increased area for fleeting charged interactions. Thus, the longer carbon chain length in octanal causes a higher boiling point. Because both octanal and butanal can participate in dipole-dipole interactions, this does not differentiate their boiling points, as it would if butane and butanal were compared. Both compounds participate in hydrogen bonding, which will account for their relatively high boiling points, but both molecules share the increased boiling point due to this type of intermolecular force.

Example Question #12 : Intermolecular Forces And Stability

Which of the following element(s) is/are not involved in hydrogen bonds?

I. Nitrogen

II. Oxygen

III. Chlorine

Possible Answers:

I and III

III only

I and II

I only

Correct answer:

III only

Explanation:

Hydrogen bonds are strong intermolecular bonds between hydrogen and one of three atoms: nitrogen, oxygen and fluorine. A typical hydrogen bond occurs between a hydrogen atom on one molecule and one of the three atoms listed on another molecule. These bonds are reversible; however, they serve as strong interactions that stabilize a mixture of molecules.

Example Question #16 : Intermolecular Forces And Stability

It is observed that molecule A has a higher boiling point than molecule B. Which of the following could be the possible identities of molecule A and molecule B?

I. Molecule A: Hydrochloric acid, Molecule B: Hydrofluoric acid

II. Molecule A: Hydrogen peroxide, Molecule B: Diamond

III. Molecule A: Diamond, Molecule B: Nitric oxide

Possible Answers:

II and III

I and II

II only

I only

Correct answer:

II only

Explanation:

Recall that boiling is the process of converting a liquid to a gas. This process involves the separation of molecules, which requires breaking the intermolecular bonds; therefore, boiling points depend on the strength of the intermolecular bonds. A stronger intermolecular bond will require more energy to break and, therefore, will have a higher boiling point. The question states that molecule A has the higher boiling point; therefore, molecule A must have stronger intermolecular interactions than molecule B. The strongest intermolecular bond is hydrogen bond, followed by dipole-dipole interactions and van der Waals interactions (weakest).

If we look at scenario I, molecule A is polar and has dipole-dipole interactions and van der Waals interactions (every molecule has van der Waals). It does not have hydrogen bonds because it does not contain nitrogen, oxygen, or fluorine (in addition the the hydrogen atom). Molecule B, on the other hand, has hydrogen bonds in addition to other intermolecular forces; therefore, molecule B has stronger intermolecular forces and a higher boiling point.

In scenario II, hydrogen peroxide has hydrogen bonds whereas diamond only has weak van der Waals interactions; therefore, molecule A has higher boiling point. In scenario III, diamond only has weak van der Waals interactions whereas nitric oxide can participate in dipole-dipole interactions as well (note that nitric oxide doesn’t have hydrogen atom and, therefore, cannot participate in hydrogen bonds). This means that molecule B has the higher boiling point in scenario III.

Example Question #12 : Intermolecular Forces And Stability

Which of the following compounds are not able to form hydrogen bonds with water?

Possible Answers:

Alkanes

Aldehydes

Ethers

Carboxylic acids

Correct answer:

Alkanes

Explanation:

This question is rather straightforward, asking us which class of compounds will not form hydrogen bonds with water.

In order to form a hydrogen bond, whether it is intermolecular or intramolecular, there needs to be a partial positively charged hydrogen atom in between two other partial negative charged atoms. These atoms tend to be highly electronegative, and are usually either nitrogen, oxygen, or flourine.

Carboxylic acids will certainly engage in hydrogen bonds. The oxygen that is double bonded to the carbon has a partial negative charge, while the carbon has a partial positive charge, just as in aldehydes and ketones. Furthermore, the hydroxyl group attached to the carbon atom can also take part in hydrogen bonds.

Ethers are compounds in which an oxygen atom is situated between two carbon atoms via single bonds. Because there is a sufficient difference in the electronegativity of oxygen and carbon, ethers are also capable of hydrogen bonding.

Alkanes are hydrocarbons. This means that the only atoms found in these molecules are carbon and hydrogen. Because there is little difference in electronegativity between carbon and hydrogen, alkanes are incapable of hydrogen bonding with water.

Example Question #11 : Intermolecular Forces And Stability

Which of these accurately describes hydrogen bonds?

Possible Answers:

They play an important role in the solvent properties of water.

They are not involved in protein structure.

They decrease the boiling point of water.

They may occur between hydrogen and chlorine.

Correct answer:

They play an important role in the solvent properties of water.

Explanation:

A hydrogen bond forms when a hydrogen attached to an electronegative atom of one molecule becomes attracted to an electronegative atom of another molecule (the electronegative atoms that may form hydrogen bonds are oxygen, nitrogen, and fluorine). Hydrogen bonds are extremely important in water molecules. The hydrogen atoms attached to the electronegative oxygen atom in water can form hydrogen bonds with the oxygen atoms of other water molecules, giving water many of its properties as a solvent.

Hydrogen bonds are also important in protein secondary structure, which is defined by the pattern of hydrogen bonds that form between the carbonyl oxygen and amine hydrogen atoms in the peptide backbone of proteins. Lastly, hydrogen bonds increase boiling point because they increase the strength of different substances.

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