MCAT Biology › Compound Identification
How many hydrogen peaks appear in the H-NMR spectrum of 3-pentanone?
2
4
5
6
10
3-pentanone contains ten hydrogens in total; however, 3-pentanone is a symmetric compound. The four hydrogens on the carbons next to the ketone have the same spin, and the six hydrogens on the methyl carbons have the same spin. The correct answer is two hydrogen peaks.
An alcohol group in a compound would result in a broad dip around what part of the infrared (IR) spectrum?
3400cm-1
1700cm-1
2800cm-1
1200cm-1
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.
How many unique peaks would one expect to see on an 1H-NMR reading of the compound shown above?
Two
Six
Four
Ten
The molecule shown is completely symmetrical. This means that the hydrogens adjacent to the two carbons on the left of the ketone and the hydrogens adjacent to the carbons on the right of the ketone will have identical splitting patterns.
Let's focus on the right side. The farthest carbon has three hydrogens that will be split by two adjacent hydrogens. The carbon between the terminal methyl and the ketone has two hydrogens, split by three. On each side we will have two 3-hydrogen triplets and two 2-hydrogen quartets, totaling two unique and distinctive peaks composed of six and four hydrogens, respectively.
As an aside, in NMR readings, if the number of protons of each peak has a common denominator, it can likely be simplified. For example, a reading of this NMR might be reduced from a 6-H peak and 4-H peak, to a 3-H and 2-H peak, respectively. Do not get confused if the number of hydrogens in the reading does not match up to the number of hydrogens in the molecule; it just means it was most likely simplified.
According to HNMR spectroscopy, which of the following molecules would result in a peak at 9.5ppm?
Acetaldehyde
Propanone
1,1-dibromoethane
2-butanol
When dealing with peaks in NMR spectroscopy, remember that withdrawing groups on a molecule will push the proton signal farther to the left, or more downfield. Aldehydes have a distinctive peak at 9.5 ppm due to the effect of the oxygen atom in close proximity to the hydrogen.
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?
1,3-dimethylhexatriene
Butadiene
1,4-pentadiene
Ethene
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.
Which of the following statements is true concerning infrared (IR) spectroscopy?
IR spectroscopy is used to determine the frequency of vibrations between atoms
The fingerprint region is most easily used to determine the functional groups in the molecule
IR spectroscopy is used to determine the shape of the carbon backbone
IR spectroscopy can be used to easily determine molecular mass
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.
Approximately where would a carbonyl peak be found on an IR spectrum?
1700cm-1
1000cm-1
2800cm-1
The peak location will vary depending on the compound being analyzed.
It is important to memorize a couple key functional groups, and where they are located on an IR spectrum. If you see a sharp peak near 1700cm-1, you can assume it is made by a carbonyl group.
Similarly, a wide peak around 3000cm-1 will be made by a hydroxyl group.
Which of the following functional groups exhibits the highest frequency in an infrared (IR) spectrum?
Alcohol
Nitrile
Ester
Ketone
Aldehyde
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.
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?
Orange or red
Blue or green
White
More information is needed in order to answer the question
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.
Synthetic testosterone is typically synthesized in yams and then used by athletes to boost their physical performance across various sports. This practice has been deemed illegal by most major sports authorities. Testing for synthetic testosterone use is accomplished by comparing the chemical composition of synthetic testosterone to natural testosterone.
Which method would be the most useful in identifying the chemical composition differences between natural and synthetic testosterone?
Mass spectrometry
Radio isotope transferance labeling
Chromatography
Magnetic resonance imaging
Mass spectrometry is used to identify the chemical composition of samples and, therefore, is the best choice to look at the differences between natural and synthetic testosterone.