MCAT Biology : Organic Chemistry, Biochemistry, and Metabolism

Study concepts, example questions & explanations for MCAT Biology

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Example Questions

Example Question #81 : Organic Chemistry, Biochemistry, And Metabolism

Determining the molecular ion peak (parent peak) in mass spectroscopy allows you to determine what characteristic of a mystery molecule?

Possible Answers:

Molecular charge

Molecular weight

Functional groups

Nuclear charge

Correct answer:

Molecular weight

Explanation:

The molecular ion peak is determined using mass spectrometry. The parent peak is formed when a mystery molecule does not fragment, and simply loses an electron. This means that the mass to charge ratio of this peak will allow us to determine the molecular weight of the compound.

Example Question #1 : Ir Spectroscopy

Which of the following statements is true concerning infrared spectroscopy?

Possible Answers:

When the infrared light frequency matches the frequency of bond vibration in a molecule, a peak is recorded on the spectrum. 

IR spectroscopy is useful in determining the size and shape of a compound's carbon skeleton.

An IR spectrometer shines infrared light on a compound and records the positions where the light is blocked by the compound. This results in the spectrum's peaks.

Functional groups can be identified by looking in the fingerprint region of the spectrum.

Correct answer:

When the infrared light frequency matches the frequency of bond vibration in a molecule, a peak is recorded on the spectrum. 

Explanation:

IR spectroscopy allows you to identify what functional groups are present in a compound. The IR spectrum is created by recording the frequencies at which a polar bond's vibration frequency is equal to the infrared light's frequency.

The fingerprint region is separate from the function group region, and generally corresponds to carbon-carbon or carbon-hydrogen interactions. While the spectrum can show what groups are present in a compound, it cannot be used to find the position of these groups or provide a carbon skeleton.

Example Question #2 : Ir Spectroscopy

Which of the following statements is true concerning infrared (IR) spectroscopy?

Possible Answers:

The fingerprint region is most easily used to determine the functional groups in the molecule

IR spectroscopy can be used to easily determine molecular mass

IR spectroscopy is used to determine the shape of the carbon backbone

IR spectroscopy is used to determine the frequency of vibrations between atoms

Correct answer:

IR spectroscopy is used to determine the frequency of vibrations between atoms

Explanation:

IR spectroscopy is most commonly used to determine the functional groups found in the molecule being observed. This is done by observing the vibration frequencies between atoms in the molecule. It does not easily reveal the size or shape of the molecule's carbon skeleton. Although the fingerprint region is unique for every molecule, it is very difficult to read when attempting to determine the molecule's functional groups. Most functional group peaks are observed in the functional group region adjacent to the fingerprint region.

Example Question #1 : Ir Spectroscopy

In IR spectroscopy, the vibration between atoms is caused by which of the following?

Possible Answers:

The number of protons in a nucleus

The movement of electrons to higher energy levels

The overall molecular weight of the molecule

Dipole moments between atoms

Correct answer:

Dipole moments between atoms

Explanation:

Infrared (IR) spectroscopy takes advantage of the electrical difference between atoms in a polar bond. These dipole moments, when exposed to infrared radiation, stretch and contract in what appears to be a vibrating motion between the atoms. The different vibrational frequencies in the molecule allow for the compound to be "read" using IR spectroscopy.

Example Question #82 : Organic Chemistry, Biochemistry, And Metabolism

Ultraviolet spectroscopy is used to detect conjugate double bonds in a compound. The longer the chain of conjugated double bonds in a compound, the longer the absorbed wavelength of UV light.

Which of the following compounds would result in the longest absorbed wavelength?

Possible Answers:

Butadiene

1,4-pentadiene

Ethene

1,3-dimethylhexatriene

Correct answer:

1,3-dimethylhexatriene

Explanation:

When predicting the absorbed wavelength, a general rule of thumb is that butadiene will absorb around  217nm. For each additional conjugated double bond, you add 30-40nm. In addition, an alkyl group will add approximately 5nm.

Since 1,3-dimethylhexatriene has three consecutive conjugated double bonds, as well as two alkyl groups attached to the conjugate system, it will have the longest absorbed wavelength.

Example Question #1 : Ir Spectroscopy

Which of the following functional groups exhibits the highest frequency in an infrared (IR) spectrum?

Possible Answers:

Ketone

Aldehyde

Ester

Alcohol

Nitrile

Correct answer:

Alcohol

Explanation:

An alcohol (-ROH) exhibits a strong, broad absorbance peak at about 3500cm-1. A nitrile's (-RCN) characteristic absorbance peak is at about 2200cm-1. Carbonyl groups have strong, sharp peaks from 1700cm-1 to 1750cm-1, depending on the type of carbonyl group. For instance, an ester (-RCO2R'-) has an absorbance at about 1750cm-1, while a ketone (-ROR'-) has an absorbance at around 1710cm-1.

Example Question #2 : Organic Chemistry

An alcohol group in a compound would result in a broad dip around what part of the infrared (IR) spectrum?

Possible Answers:

2800cm-1

1200cm-1

1700cm-1

3400cm-1

Correct answer:

3400cm-1

Explanation:

There are a couple of key functional group spectra that you must memorize. A carbonyl group will cause a sharp dip at about 1700cm-1, and an alcohol group will cause a broad dip around 3400cm-1.

Example Question #63 : Analytical Chemistry

An unknown compound is analyzed using infrared spectroscopy. A strong, sharp peak is observed at a frequency of 1750cm-1. What functional group is present?

Possible Answers:

Unsaturated ketone

Saturated ketone

Ester

Alcohol

Nitrile

Correct answer:

Ester

Explanation:

An ester has a characteristic IR absorption at about 1750cm-1. A saturated ketone has an absorption at about 1710cm-1, while an unsaturated ketone has an absorption between 1650cm-1 and 1700cm-1. A nitrile has an IR frequency of about 2200cm-1, while an alcohol has a strong, broad peak at about 3400cm-1.

Carbonyl compounds all have peaks between roughly 1650cm-1 and 1750cm-1. Ketone peaks are generally observed at the lower end of this range, while aldehydes and esters are toward the higher end of the range.

Example Question #1 : Ir Spectroscopy

An IR spectrum reading is taken before and after treating acetone with the reducing agent . What IR peak readings would be seen for the reactant acetone and for the predicted product?

Possible Answers:

Correct answer:

Explanation:

Treating acetone, a secondary carbonyl, with a reducing agent, such as sodium borohydride (NaBH4), will yield a secondary alcohol as the product.

When using IR spectroscopy, carbonyl (C=O) groups display characteristic peaks at approximately 1700cm-1, while alcohol groups (O-H) display characteristic peaks around 3300cm-1. The acetone would, therefore, initially have a characteristic peak at roughly 1700cm-1. After the reduction reaction is complete, the resulting 2-propanol would display a characteristic peak roughly at 3300cm-1.

Example Question #83 : Organic Chemistry, Biochemistry, And Metabolism

The visible spectrum is typically between 390-700nm. Shorter wavelengths are responsible for the purple end of the color spectrum, while red is perceived in the eye from the longer wavelengths. -carotene is able to absorb light at a maximum value of 497nm. 

Based on this information, what color does the eye perceive -carotene to be?

Possible Answers:

More information is needed in order to answer the question

White

Blue or green

Orange or red

Correct answer:

Orange or red

Explanation:

The wavelength of 497nm corresponds to a blue-green color, however -carotene absorbs this wavelength. This means it reflects the complementary color on the opposite end of the color spectrum. This gives -carotene a red-orange appearance, as only the reflected wavelengths will be returned to the eye.

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