Biological Molecules - Organic Chemistry

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Question

The Fischer projection pictured is a form of glucose. The carbon labeled "x" is the chiral carbon farthest away from carbon 1 and the hydroxyl group connected to carbon "x" is on the right. This fact designates that the glucose as what configuration?

D configuration

Answer

The chiral carbon farthest away from carbon 1 is designated as "D" if its hydroxyl group is on the right side in the Fischer projection. In other words, this is D-glucose because the hyroxyl group on carbon "x" is oriented to the right.

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Question

What is the name of the aldose pictured in this Fischer projection?

D ribose

Answer

The structure is D-ribose because it is a five-carbon aldose with the hydroxyl groups on carbons 2, 3, and 4 all on the right in the Fischer projection.

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Question

Which of the following statements is true regarding carbohydrates?

Answer

All of these statements are true. A carbohydrate is said to have a "D" conformation in its acyclic form when the alcohol group on the carbohydrate's top stereocenter is on the right side in a Fischer projection. Most carbohydrates that we deal with in organic chemistry are aldoses, which means that they contain an aldehyde. The anomeric carbon is the site of attachment from one monosaccharide to another, and can be used to create polysaccharides.

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Question

What is the name of the following carbohydrate?

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Answer

Stereochemistry from second to fifth carbon is R, S, S, R, which indicates D-galactose. The Haworth structure is a six-membered ring, so the molecule is in its pyranose form. The molecule has its anomeric hydroxyl group pointing down, so it's the alpha anomer.

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Question

What is the name of the following molecule?

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Answer

Stereochemistry from second to fifth carbon is R, S, R, R, which indicates D-glucose. The Haworth structure is a five-membered ring, so the molecule is in its furanose form. The molecule has its anomeric hydroxyl group pointing down, so it's the alpha anomer.

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Question

What is the name of the pictured fatty acid?

Arachidonic acid

Answer

The pictured structure represents arachidonic acid due to the 20-carbon carboxylic acid chain with characteristic unsaturated (double) bonds after carbons 5, 8, 11, and 14.

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Question

Other than the traditional numerical system, the X marking the terminal carbon in the structure shown here can be labeled how?

Linoleic acid x

Answer

Fatty acids can be labeled numerically from 1-X, or they can be labeled in reverse starting with omega-1 as the terminal carbon.

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Question

Identify the common name of the fatty acid shown here.

Real oleic acid

Answer

Oleic acid is a fatty acid consisting of 18 carbon molecules and a single unsaturated (double) bond after carbon 9, as pictured.

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Question

What type of lipid is shown below?

Triglyceride

Answer

A triglyceride consists of three fatty acid chains bound to a glycerol backbone via ester bonds, as shown by the pictured structure.

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Question

Three fatty acid chains can be bound to a glycerol backbone via ester bonds to form a triglyceride. What type of chemical reaction is this?

Answer

The reaction described is an esterification in which water is a product—as is characteristic of a condensation reaction—and in which an ester bond is formed to connect the fatty acid chain and the glycerol molecule.

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Question

An unknown molecule was found to have a molecular formula of . This molecule can be identified as a __________.

Answer

This question is a little bit tricky. At first glance, we would jump to the conclusion that this molecule is a long hydrocarbon chain attached to a carboxylic acid and, therefore, a fatty acid. The premise is correct. However, our conclusion is false because, by convention, a fatty acid must contain a carbon chain of at least 12 carbons. The given formula does not match the description for a steroid or triacylglycerol. The correct answer is none of these.

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Question

What is the primary biological function of a fatty acid?

Answer

The primary biological function of a fatty acid is to serve as a medium for the derivation of other important lipids such as waxes, triacylglycerols, phospholipids, and other necessary lipids.

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Question

Before the advent of synthetic soap, hand soap was made from animal fat, namely triacylglycerols. What property of triacylglycerols make them an ideal component in hand soap?

Answer

A triacylglycerol is derived from the hydrolysis of glycerols and fatty acids. Triacylglycerols have hydrophobic hydrocarbon tails and hydrophilic heads (amphipathic). The hydrophobic tails dissolve into dirt/grease on the skin while the hydrophilic tails work with running water to suspend and remove the dissolved impurities.

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Question

Based on the formula and structure of this molecule, this molecule can be classified as a __________.

Answer

The correct answer is the lipid, wax. Lipids can often be identified based on their structure alone. The general structure of wax is an ester with two long carbon chains on each end of the ester, as seen in this problem. Additionally, fatty acids can be identified simply as long carbon chains with a carboxylic acid on one end, while the general structure of steroids can be seen as four connected hydrocarbon rings.

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Question

The following terpene is classified as which of the following?

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Answer

The molecule's skeletal structure contains two isoprene (2-methylbutyl) units, and therefore the molecule is a monoterpene.

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Question

Which of the following compounds are isomers?

Answer

By definition, isomers are compounds that share the same molecular formula but have differing molecular structures. 1-butanol and 2-butanol share the same formula, but the hydroxyl group can be located on either the first or second carbon on the molecule, yielding two different structures that share the same molecular formula. The other answers have different molecular formulas and are thus not isomers.

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Question

By which characteristic do resonance structures of a molecule differ?

Answer

By definition, resonance structures are multiple Lewis structures that depict the same molecular compound. The only difference pertains to the way in which electrons are shared by atoms in the molecule. Molecules are weighted averages of their most stable resonance contributors.

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Question

Pinene

How many isoprene units does the given molecule, alpha-pinene, have?

Answer

Alpha-pinene is a terpene, and is thus composed of isoprene units. A single isoprene unit has 5 carbon atoms. This molecule has 10 carbons, thus it contains 2 isoprene units.

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Question

Cholic acid 3d

What class of biological molecule is the given compound?

Answer

This is cholic acid, a steroid. Steroids can be easily identified by their characteristic fused ring structures.

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Question

Which of the atoms in the molecules below is/are sp 2 hybridized?

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Answer

The boron in 2 is sp 3 hybridized because of its four substituents and the carbon in 4 is sp hybridized because of its connection to only the nitrogen with a single .

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