Functional Groups and Properties

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MCAT Biology › Functional Groups and Properties

Questions 1 - 10
1

Ephedrine (shown below) contains what type of amine?

Mcat_problem_set_1

Secondary

Primary

Tertiary

Quaternary

Neutral

Explanation

A secondary amine is an amine (nitrogen atom) that is attached to two carbon-containing groups (alkyl groups or aryl groups). The nitrogen in ephedrine is attached to two alkyl groups, making it a secondary amine.

Primary amines are generally written as . Secondary amines are generally written as . A tertiary amine will be bound to three different R-groups. Quaternary amines require a positive charge on the nitrogen atom to accommodate a fourth R-group.

2

Carboxylic acids typically have higher boiling points than aldehydes and ketones. This is because carboxylic acids have which of the following properties?

Carboxylic acids can create intermolecular hydrogen bonds, increasing the effective molecular weight of the molecules

Carboxylic acids can create intramolecular hydrogen bonds, which increases the boiling point

Carboxylic acids are less soluble in water than aldehydes and ketones

Aldehydes and ketones create stronger hydrogen bonds with water

Explanation

Carboxylic acids are able to create hydrogen bonds with one another. This forms a dimer, which doubles the effective molecular weight and greatly increases the boiling point of carboxylic acids. Aldehydes and ketones are not able to form hydrogen bonds with one another, so their boiling points are dependent on each individual molecule's molecular weight. As a result, their boiling points are not as high as the corresponding carboxylic acids'. Note that carboxylic acids cannot form intramolecular hydrogen bonds.

3

Which of the following compounds will be the most reactive with an alcohol to form an ester product?

Acid chloride

Acid anhydride

Carboxylic acid

Amide

Explanation

All of the options, except for the carboxylic acid itself, are derivatives of a carboxylic acid. These derivatives differ in their reactivity when creating new compounds. Acid chlorides are the most reactive compounds, and amides are the least reactive out of these option. Acid chlorides and acid anhydrides frequently participate in reactions, while amides are less likely to react.

4

In the reaction scheme below, compound A is a(n) __________ and compound B is a(n) __________.

Mcat_1

ketone . . . alcohol

alcohol . . . ketone

ketone . . . alkene

alkene . . . alcohol

alcohol . . . alkene

Explanation

Ketones, like compound A, contain an internal carbon-oxygen double bond. Alcohols, like compound B, contain a hydroxyl group (-OH). In this case, compound A is a secondary ketone and compound B is a tertiary alcohol.

Alkenes, like compound C, contain a carbon-carbon double bond.

5

Compound A, shown below, contains an example of what type of functional group?

Mcat_2

Ester

Ketone

Carboxylic acid

Ether

Nitrile

Explanation

Esters have the general molecular formula of , where and are carbon groups. The rightmost region of compound A shows an ester.

Ketones have the formula of , with a carbon-oxygen double bond. Ethers have the formula of , with an oxygen linked by single bonds within a carbon chain. An ester resembles adjacent ketone and ether groups. Carboxylic acids have the formula , resembling an ester with a hydrogen in place of a second carbon chain. Finally, the nitrile group has a formula of , with a triple bond between nitrogen and carbon.

Compound A also contains an aromatic function group (the benzene ring) and a nitro group, , on the far left side.

6

Drain cleaners a common household staple, used to open clogged drains in bathtubs and sinks. Human hair is a common culprit that clogs pipes, and hair is made predominately of protein. Drain cleaners are effective at breaking down proteins that have accumulated in plumbing. Drain cleaners can be either acidic or basic, and are also effective at breaking down fats that have accumulated with proteins.

A typical reaction—reaction 1—which would be expected for a drain cleaner on contact with human hair, would be as follows in an aqueous solution:

Pic_1

Another reaction that may occur, reaction 2, would take place as follows in an aqueous solution:

Pic_2

Compared to the organic compound produced in Reaction 2, an aldehyde __________.

has lower acidity

has no carbonyl group

has more polarity in its bonds

is more oxidized

has lower overall bond energy

Explanation

Aldehydes have lower acidity than carboxylic acids, but are more reduced and thus have higher overall bond energies.

7

Which of the following functional groups would most likely act as an acid?

Carboxyl

Acetal

Aldehyde

Ketone

Explanation

Carboxyl groups, or carboxylic acids, are good acids due to the resonance between the two oxygen atoms, allowing for greater stability of the conjugate base upon removal of a proton. Acetals and aldehydes can act as weak acids, but carboxyl groups will be deprotonated first.

8

Understanding the function of the sodium-potassium pump, which of the following residues might possibly line the channel?

Aspartic acid

Lysine

Isoleucine

Oleic acid

Explanation

Aspartic acid is the only viable answer. Its R-group contains a second carboxylic acid that is deprotonated in most physiological conditions. The negatively charged aspartate will interact favorably with the positively charged cations moving through the pump. Lysine is a basic amino acid that contains an amine group at the terminal end of its R-group. Isoleucine is an aliphatic and hydrophobic amino acid. Oleic acid is an example of a fatty acid, which can carry a negative charge in some conditions, but it is not an amino acid and thus cannot be incorporated into a protein.

9

Your lab isolates a compound with the formula . Upon further analysis, you determine that the base structure is a benzene ring with a single constituent. Which of the following could be the identity of the compound?

Benzylamine

Benzylamide

Benzylmethylamine

Nitrobenzene

None of these

Explanation

Nitro groups and amide groups both contain oxygen components, and cannot be found in the compound described. We also know that the benzene ring only has a single constituent, meaning that it cannot be a methylamine. The compound must be benzylamine, a benzene ring with a -CH2NH2 substituent.

10

Among the most important pH buffer systems in humans is the bicarbonate buffer, which keeps the blood at a remarkably precise 7.42 pH. The bicarbonate buffer system uses a series of important compounds and enzymes to make the system function. Figure 1 depicts the key reactions that take place.

Untitled

The activity of this buffer system is mainly controlled by the renal and respiratory systems. The renal system excretes bicarbonate in the urine, while the respiratory system “blows off” carbon dioxide as needed. By balancing these two systems as needed, blood pH is maintained in such a narrow range.

The deprotonation of carbonic acid is favored by __________.

resonance stabilization in bicarbonate

a buildup of bicarbonate in the system

a loss of CO2 from the system

resonance stabilization in carbonic acid

resonance stabilization in carbon dioxide

Explanation

Bicarbonate is the product of deprotonation of carbonic acid. Anything that stabilizes this product will encourage the deprotonation reaction, and resonance is a key stabilizing factor for bicarbonate. Stability of the conjugate base is a major contributing factor to the strength of an acid and its ability to deprotonate.

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