MCAT Biology : Molecular Properties

Study concepts, example questions & explanations for MCAT Biology

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Example Questions

Example Question #1 : Functional Groups And Properties

Drain cleaners are 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

The NH4 molecule produced in Reaction 2 must have __________.

Possible Answers:

a basic nature due to the presence of the nitrogen atom

a positive charge due to the presence of an extra hydrogen

no charge, since N has a lone pair of electrons available to bond

a negative charge, since one was also created on the other product

an expanded octet for the N atom

Correct answer:

a positive charge due to the presence of an extra hydrogen

Explanation:

The additional H present on ammonia (NH3) requires the generation of the a positive charge on the molecule. This also must be created to balance the negative charge created on the associated anion product.

Example Question #3 : Functional Groups And Properties

Which of the following amines is the strongest base?

Possible Answers:

A secondary amine with electron-withdrawing functional groups

A secondary amine with electron-donating functional groups

A primary amine with an electron-donating functional group

Ammonia

Correct answer:

A secondary amine with electron-donating functional groups

Explanation:

Amines act as bases due to the lone pair on the nitrogen. Amine basicity can be increased or decreased by functional groups attached to the nitrogen. Electron-withdrawing groups decrease the basicity of an amine by lessening the effect of the lone pair, while electron-donating groups increase basicity by amplifying the lone pair effect. As a result, a secondary amine with an electron-donating functional groups will be the most basic amine.

Example Question #1 : Amine Chemistry

Ephedrine (shown below) contains what type of amine?

Mcat_problem_set_1

Possible Answers:

Neutral

Tertiary

Secondary

Quaternary

Primary

Correct answer:

Secondary

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.

Example Question #2 : Functional Groups And Properties

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?

Possible Answers:

Benzylamide

Benzylmethylamine

None of these

Nitrobenzene

Benzylamine

Correct answer:

Benzylamine

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.

Example Question #2 : Functional Groups And Properties

What is the name of the functional group that contains a vinylic hydroxyl group?

Possible Answers:

Carboxyl

Keto

Aldehyde

Enol

Correct answer:

Enol

Explanation:

Enol functional groups contain a hydroxyl group bonded to a carbon involved in a double bond with another carbon (vinyl carbon). An enol will usually undergo tautomerization to become a more stable keto.

Example Question #3 : Functional Groups And Properties

Ephedrine, whose structure is shown below, is used commonly as a stimulant and decongestant.

Mcat_problem_set_1

Ephedrine contains all of the following functional groups except __________.

Possible Answers:

amine

ketone

arene

alcohol

N-methyl group

Correct answer:

ketone

Explanation:

Ephedrine contains an arene (the aromatic benzene ring), an alcohol (the -OH group), an amine (the nitrogen-based group), and an N-methyl group (-CH3 attached to nitrogen). It does not contain a ketone (C=O), or any other carboxyl groups.

Example Question #4 : Functional Groups And Properties

Which of the following compounds would you expect to undergo a nucleophilic addition reaction?

Possible Answers:

Acetic acid

Ethanamide

Methyl ethanoate

Propanal

Correct answer:

Propanal

Explanation:

When dealing with carbonyl compounds, remember that a carboxylic acid and all of its derivatives will undergo nucleophilic substitution. Aldehydes and ketones will undergo nucleophilic addition. Propanal is a three-carbon aldehyde, and will thus undergo nucleophilic addition.

Acetic acid is a carboxylic acid, methyl ethanoate is an ether, and ethanamide is an amide; each of these would undergo nucleophilic substitution.

Example Question #1 : Functional Groups And Properties

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

Mcat_2

Possible Answers:

Carboxylic acid

Nitrile

Ester

Ketone

Ether

Correct answer:

Ester

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.

Example Question #11 : Functional Groups And Properties

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.

Which of the following would be expected pKa values for carbonic acid and carbonate, respectively?

Possible Answers:

1.4 * 10-14 and 14

pKa values depend on surrounding conditions

6.3 and 10.3

10.3 and 6.3

14 and 1.4 * 10-14

Correct answer:

6.3 and 10.3

Explanation:

Carbonic acid is a weak organic acid, not nearly as strong as most inorganic acids. It is still, however, an acid, and has a pKa below 7, but nowhere near as low as 1.4 * 10-14.

Carbonate is a conjugate base, and thus has an alkaline pKa around 10.3.

Example Question #361 : Organic Chemistry, Biochemistry, And Metabolism

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 __________.

Possible Answers:

resonance stabilization in carbonic acid

a loss of CO2 from the system

resonance stabilization in bicarbonate

resonance stabilization in carbon dioxide

a buildup of bicarbonate in the system

Correct answer:

resonance stabilization in bicarbonate

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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