Organic Chemistry, Biochemistry, and Metabolism

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MCAT Biology › Organic Chemistry, Biochemistry, and Metabolism

Questions 1 - 10
1

Acetyl-CoA is a react in the citric acid cycle, while and are products. If twelve molecules of are produced over a period of time, how many molecules are produced during this period?

Four

Twelve

Twenty-four

Two

Explanation

Each turn of the citric acid cycle is powered by one molecule of acetyl-CoA, resulting in three and one . The net reaction is:

Since twelve are produced, there must have been an input of four acetyl-CoA molecules and four total turns in the cycle. As a result, four molecules were produced.

2

Which alcohol will react most rapidly via an SN1 mechanism?

Explanation

Tertiary alcohols react most rapidly via SN1 mechanisms because they form stable tertiary carbocations. Primary and secondary alcohols typically react most rapidly via SN2 mechanisms.

Of the available options, is the only one that contains a tertiary alcohol.

3

Organic reactions can often be classified into two broad categories: substitution and elimination. Substitution reactions substitute one substituent for another. Elimination reactions typically form after the wholesale removal of a substituent, with no replacement. Below are examples of two types of reactions.

Reaction 1:

1

Reaction 2:

2

A scientist is studying the rate of reaction 1. He wants to double the rate of the reaction, but is unsure how to increase concentrations of the reactants. Which of the following is true?

Doubling the concentrations of both the hydroxide and the halide will quadruple the reaction rate

Doubling the concentration of the halide only will quadruple the reaction rate

Doubling the concentration of the hydroxide only will quadruple the reaction rate

Neither doubling the concentration of halide, nor doubling the concentration of hydroxide, will quadruple the reaction rate

Reaction rate in this reaction is not determined by concentration

Explanation

Reaction 1 represents an SN2 reaction. The rate limiting step involves both reactants coming together to form a transition state. The rate of this reaction depends on the concentration of both the organic molecule and the nucleophile.

In contrast, reaction 2 is an E1 reaction, in which the rate limiting step is the removal of the leaving group to form a carbocation. In E1 and SN1 reactions, adjusting the concentration of the halide only is enough to affect the rate.

4

How many chiral centers does the following molecule contain?

Chiral_centers

1

0

2

3

4

Explanation

A chiral center is defined as a tetrahedral atom with four unique substituents. In the molecule above there exists only one carbon that has four different substituents, which is carbon #4 (counting from the right). Carbon #4 has -chloro and -hydroxy groups, as well as two different longer alkyl chains. No other atom has four unique substituents.

5

Organic reactions can often be classified into two broad categories: substitution and elimination. Substitution reactions substitute one substituent for another. Elimination reactions typically form after the wholesale removal of a substituent, with no replacement. Below are examples of two types of reactions.

Reaction 1:

1

Reaction 2:

2

A scientist is studying the rate of reaction 1. He wants to double the rate of the reaction, but is unsure how to increase concentrations of the reactants. Which of the following is true?

Doubling the concentrations of both the hydroxide and the halide will quadruple the reaction rate

Doubling the concentration of the halide only will quadruple the reaction rate

Doubling the concentration of the hydroxide only will quadruple the reaction rate

Neither doubling the concentration of halide, nor doubling the concentration of hydroxide, will quadruple the reaction rate

Reaction rate in this reaction is not determined by concentration

Explanation

Reaction 1 represents an SN2 reaction. The rate limiting step involves both reactants coming together to form a transition state. The rate of this reaction depends on the concentration of both the organic molecule and the nucleophile.

In contrast, reaction 2 is an E1 reaction, in which the rate limiting step is the removal of the leaving group to form a carbocation. In E1 and SN1 reactions, adjusting the concentration of the halide only is enough to affect the rate.

6

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.

7

Which of the following statements is true concerning the Hofmann elimination reaction?

The least substituted alkene is the major product in the reaction

The ammonium is eliminated following an E1 mechanism

The Zaitsev product is favored in the elimination reaction

The quaternary ammonium salt is a poor leaving group

Explanation

The Hofmann product is the most favored product in a Hofmann elimination reaction. The reaction follows an E2 mechanism, where a quaternary ammonium salt is able to be removed from a hydrocarbon, resulting in an alkene product. This reaction results in the least substituted alkene being the primary product.

8

Which answer choice is an enantiomer of the molecule shown below?

Molecule_1

Molecule_2

Molecule_3

Molecule_4

Molecule_5

Molecule_1

Explanation

An enantiomer is defined as a stereoisomer that is a mirror image of another. In other words, if a molecule was placed in front of a mirror, its mirror image would be the enantiomer. Questions such as these require a bit of visualization, but should be easy points. In addition, if you see the answer choice quickly and are confident in your decision, move onto the next question without spending time on the other choices, as mental geometry and visualization may take more time than anticipated.

9

What is the purpose of the formation of lactic acid during anaerobic respiration?

It allows NAD+ to reform

It allows NADH to reform

It allows FAD to reform

It allows FADH2 to reform

It allows glucose to reform

Explanation

Cells need a constant supply of NAD+ to accept electrons during glycolysis in order to produce pyruvate from glucose.

10

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.

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