Organic Chemistry : Organic Concepts

Study concepts, example questions & explanations for Organic Chemistry

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Example Questions

Example Question #271 : Organic Concepts

What is the order of increasing stability for the following ions going from least to greatest?

1. 

2.  

3. 

4. 

Possible Answers:

Correct answer:

Explanation:

The bigger the ion, the more stable it is, because the negative charge is distributed over a larger area.

Example Question #341 : Organic Chemistry

Which of the following statements best explains why the element carbon can make up the structure of a plethora of compounds?

Possible Answers:

Carbon atoms have very high electronegativity, a characteristic which allows them to bond with other atoms

Carbon readily forms ionic bonds with other carbon atoms

Carbon atoms combine very readily with oxygen atoms

Carbon can form up to four covalent bonds, often with other carbon atoms

Correct answer:

Carbon can form up to four covalent bonds, often with other carbon atoms

Explanation:

Carbon is a tetravalent element, meaning it can form up 4 covalent bonds with other elements, especially other carbon atoms. This allows for the formation of many different carbon-containing elements of differing sizes, shapes, and structures.

Example Question #342 : Organic Chemistry

Which of the following compounds is a saturated hydrocarbon?

Possible Answers:

Propyne

Propene

Propane

Benzene

Correct answer:

Propane

Explanation:

By definition, a saturated hydrocarbon is a compound that contains no double or triple bonds-all single bonds. Of these choices, propane (-ane suffix indicates that it is an alkane, which contains only single bonds) is the only saturated hydrocarbon.

Example Question #343 : Organic Chemistry

Hexane is an example of an __________ solvent.

Possible Answers:

polar protic

polar aprotic

nonpolar protic

nonpolar aprotic

Correct answer:

nonpolar aprotic

Explanation:

Hexane is a hydrocarbon consisting of 6 carbon atoms and 12 hydrogen atoms, making it nonpolar. Because it has no donatable hydrogen ions, it is also considered aprotic.

Example Question #274 : Organic Concepts

What substituent in the X-position would result in the product?

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Possible Answers:

Correct answer:

Explanation:

The inductive effect of the  group stabilized the carbocation further away from the electron withdrawing group, causing the addition of the  to occur there.

Example Question #344 : Organic Chemistry

How many sigma bonds does a double bond contain?

Possible Answers:

None

Correct answer:

Explanation:

A double bond contains one sigma bond and one pi bond.

Example Question #52 : Intermolecular Forces And Stability

How many sigma and pi bonds does a triple bond contain?

Possible Answers:

 and 

 and 

 and 

 and 

 and 

Correct answer:

 and 

Explanation:

A triple bond contains 2 pi bonds and a single sigma bond. 

Example Question #51 : Intermolecular Forces And Stability

Which of the following functional groups would stabilize a Grignard reagent? 

Possible Answers:

Correct answer:

Explanation:

A Grignard reagent is equivalent to a carbanion. Electron withdrawing groups help stabilize the negative charge on the carbon while electron donating groups will destabilize it. Therefore,  is the only correct answer. 

Example Question #55 : Intermolecular Forces And Stability

Which of the following compounds does not have a net dipole moment?

Possible Answers:

Carbon dioxide

Carbon monoxide

Correct answer:

Carbon dioxide

Explanation:

In this question, we're asked to identify a compound that has no dipole moment.

To answer this question, we need to understand what a dipole moment is. Some compounds have an uneven distribution of charge around their molecular structure. This uneven distribution is normally due to differences in electronegativity of the various atoms that make up that molecule. This uneven distribution of electrical charge is what is known as a molecule's dipole moment. However, while electronegativity differences are important, it is also vital to take into consideration the molecular structure of the compound in question because, many times, two dipole moments can cancel each other out and lead to a net dipole moment of zero.

Now, we'll need to look at each answer choice in order to see whether there will be an uneven distribution of electrical charge.

First, let's start with water. We know that water consists of an oxygen atom singly bound to two other hydrogen atoms. Furthermore, the oxygen has two lone pairs of electrons. This causes the water molecule to take on a bent shape. Moreover, the electronegativity of oxygen is much greater than that of hydrogen. Consequently, we can expect there to be a net dipole moment in water.

Next, let's take a look at dichloromethane, . In an ordinary molecule of methane, we know that the four hydrogen atoms are situated around the central carbon atom in a tetrahedral fashion. Likewise, dichloromethane also has a tetrahedral structure. The difference, however, is that two of the hydrogens are now chlorine atoms. As a result, two of the chlorine atoms will be pointed in the opposite direction to the two hydrogen atoms. Furthermore, chlorine and carbon have a massive difference in electronegativity. As a result, we would expect dichloromethane to have a net dipole moment.

Let's turn our attention to carbon monoxide. This compound consists of a carbon atom triple bonded to an oxygen atom, with a lone pair of electrons on both atoms. Since these are the only two atoms in the compound, the structure is relatively simple as it is just linear. Moreover, there is a substantial difference in the electronegativity of carbon and oxygen and, thus, we would expect carbon monoxide to have a net dipole moment.

Finally, let's look at carbon dioxide. In this compound, we have a central carbon atom which is double bonded to two other oxygen atoms. Just as with carbon monoxide, the structure of carbon dioxide is simply linear. And once again, due to the difference in electronegativity between carbon and oxygen, there is a dipole moment between the central carbon atom and each of the oxygen atoms. However, this doesn't mean that the molecule as a whole has a dipole moment!! Remember, we also need to take the structure of the molecule into account. Because the two oxygen atoms are arranged around the carbon in a linear fashion and are pointing directly away from each other, the two dipole moments between carbon and oxygen will exactly cancel each other out. Thus, carbon dioxide will not have a net dipole moment.

Example Question #271 : Organic Concepts

Shown below is the molecule known as pyrrole. Pyrrole is an aromatic compound that is quite stable due to resonance.

Pyrrole

Which of the following depicts a valid resonance structure for pyrrole?

Possible Answers:

Pyrrole resonance wrong 2

Pyrrole resonance wrong 3

Pyrrole resonance correct

Pyrrole resonance wrong

Correct answer:

Pyrrole resonance correct

Explanation:

In this question, we're presented with the structure of pyrrole. We're told that the compound is aromatic and is stabilized by resonance. We're then given a number of resonance structures, and we're asked to decide which is a correct one.

In order to answer this question, we'll need to consider the structure of pyrrole, and see which resonance structures we can obtain. To do this, we'll need to do some electron pushing.

Also, it's critical to recognize that the nitrogen atom in pyrrole has a lone pair of electrons. This lone pair is situated in the nitrogen's p orbitals. This allows the p orbital electrons to participate in pi bonding with the other two carbon-carbon double bonds found in the molecule. Because there is a lone pair of electrons on the nitrogen atom, we can begin our "electron pushing" starting with these electrons first.

Pyrrole resonance mechanism

After pushing electrons as shown above, we end up with the following possible resonance structure.

Pyrrole resonance correct

Thus, this is the correct answer. All of the other resonance structures shown are not possible. You can do electron pushing to try it out for yourself.

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