Organic Chemistry : Organic Concepts

Study concepts, example questions & explanations for Organic Chemistry

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Example Questions

Example Question #201 : Organic Concepts

Alpha-D-glucopyranose:

Screen shot 2015 11 21 at 4.32.55 pm

Glucose (pictured) is defined as which of the following?

Possible Answers:

Ketohexose

Aldohexose

Ketopentose

Aldopentose

Triose phosphate

Correct answer:

Aldohexose

Explanation:

Glucose in its open chain form (shown below), has a free aldehyde group (an aldose), and it contains six carbons (a hexose). Together, glucose is shown to be an aldohexose.

Screen shot 2015 11 21 at 4.46.41 pm

Example Question #202 : Organic Concepts

Alpha-D-glucopyranose

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Which of the labelled carbon atoms is the anomeric carbon?

Possible Answers:

D

A

B

E

C

Correct answer:

A

Explanation:

The anomeric carbon is formed from the original carbonyl carbon in the straight-chain form of the molecule being attacked by a hydroxyl group to form a hemiacetal. This is seen as a carbon that is bonded to two oxygen atoms. In the case of glucose, the carbon labelled A is a hemiacetal, and is considered to be the anomeric carbon.

Example Question #13 : Help With Organic Carbohydrates

Shown below is the structure of a sugar molecule.

Sugar

Which of the following is the most appropriate classification of this sugar?

Possible Answers:

Ketoheptose

Aldoheptose

Aldohexose

Ketohexose

Correct answer:

Aldoheptose

Explanation:

In this question, we're given the structure of a sugar molecule, and we're asked to identify which answer choice represents the correct identification of this molecule.

To answer this question, there are two things we need to look at. For one, we need to determine whether it is an aldehyde sugar (aldose) or a ketone sugar (ketose). The first carbon atom in the molecule (shown at the very top in the image) is shown as . This means that the carbon contains a double bond to the oxygen. Furthermore, since it also contains a bond to a hydrogen, we can conclude that this is an aldehyde functional group. Consequently, we know that this must be an aldose sugar.

Next, we need to look at the number of carbon atoms in the molecule. In the image shown in the question, there are a total of seven carbon atoms. Thus, this sugar would be classified as a heptose sugar (seven carbons) rather than a hexose sugar (six carbons).

Putting these two pieces of information together, we know that the sugar is both an aldose and a heptose. Therefore, this sugar is an aldoheptose.

Example Question #1 : Help With Organic Proteins

Which of the following is an example of a basic amino acid?

Possible Answers:

Lysine

Alanine

Aspartic acid

Leucine

Tyrosine

Correct answer:

Lysine

Explanation:

Lysine's R-group includes an amine (-NH2), which can be ionized by picking up a hydrogen. This ability classifies lysine as basic.

Example Question #1 : Sulfide Chemistry

Which of the following amino acids can participate in the formation of a disulfide bridge?

Possible Answers:

Alanine

Tyrosine

Aspartic acid

Phenylalanine

Cysteine

Correct answer:

Cysteine

Explanation:

Cysteine's R-group contains a sulfhydryl group (-SH), which can participate in the formation of a disulfide bridge in a protein's tertiary and/or quaternary structure. Cysteine is the only amino acid to contain a sulfur atom.

Example Question #3 : Help With Organic Proteins

Which of the following amino acids is the only one to contain a side chain that results in an achiral amino acid?

Possible Answers:

Lysine

Aspartic acid

Alanine

Glycene

Correct answer:

Glycene

Explanation:

The only achiral amino acid is Glycene. Glycene's side chain is simply a hydrogen. Because a hydrogen already exists on the fundamental structure of an amino acid backbone, a side chain of a single hydrogen atom causes glycene to be achiral.

Example Question #2 : Help With Organic Proteins

How many essential amino acids are there?

Possible Answers:

Ten

Zero

Twelve

Twenty

Nine

Correct answer:

Nine

Explanation:

The nine essential amino acids are valine, leucine, isoleucine, histidine, phenylalanine, tryptophan, methionine, threonine, and lysine. These amino acids must be consumed in the diet, since they cannot be synthesized by adult humans.

Example Question #31 : Biological Molecules

What is the D/L configuration and the absolute (R/S) configuration of the following amino acid (cysteine)?

Screen shot 2015 11 16 at 1.06.26 pm

Possible Answers:

L, R

D, R

L, S

Cysteine is achiral

D, S

Correct answer:

L, R

Explanation:

Cysteine is an unusual amino acid. Although each of the normal biological amino acids have the L configuration (with the exception of glycine, which is achiral), meaning they can be drawn with the Fischer projection as shown:

 Screen shot 2015 11 16 at 1.10.31 pm

the fact that cysteine contains a sulfur group makes the side chain a higher priority than the carboxylic acid. Therefore, the absolute configuration of cysteine will be R, and not S like the other amino acids.

Example Question #1 : Help With Organic Proteins

Consider L-glutamate, which is shown below.

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Using the pKa information provided, what is the isoelectric point (pI) of the given molecule?

Possible Answers:

Correct answer:

Explanation:

The isoelectric point is the average of the two pKa values around which the molecule has an overall neutral charge. In the case of glutamate, the amino acid is in its neutral (zwitterion) form in between the lower two pKa values. Taking the average of the two values gives the pI.

Example Question #1 : Help With Organic Proteins

Consider the amino acid L-lysine, shown below.

Screen shot 2015 11 16 at 1.44.03 pm

Given the pKa values shown, calculate the pI of lysine.

Possible Answers:

Correct answer:

Explanation:

The isoelectric point is the average of the two pKa values around which the molecule has an overall neutral charge. In the case of lysine, the amino acid is in its neutral (zwitterion) form in between the higher two pKa values. Taking the average of the two values gives the pI.

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