Biochemistry Identification Quiz: Stereoisomerism to Cyclic Forms of Monosaccharides

Practice flashcards created from the biochemistry identification quiz on stereoisomerism, Fischer projection formulas, enantiomer properties, chiral compounds, carbohydrate classification, and cyclic forms of monosaccharides.

What term describes isomers that have the same molecular and structural formulas but differ in the orientation of atoms in space?

Stereoisomers

What are stereoisomers whose molecules are nonsuperimposable mirror images of each other called?

Enantiomers

What are stereoisomers whose molecules are not mirror images of each other called?

Diastereomers

What is a molecule with a carbon atom attached to four different groups called?

Chiral molecule

What are diastereomers that differ only in the configuration at one chiral center called?

Epimers

What formula is used to calculate the maximum number of stereoisomers?

$$2^n$$

Who was the German chemist who developed the two-dimensional system for specifying chirality?

Hermann Emil Fischer

What is the two-dimensional structural notation used to show the spatial arrangement of groups about chiral centers?

Fischer projection formula

What is a monosaccharide whose -OH on the penultimate carbon is on the right in a Fischer projection called?

D-Monosaccharide

What is a monosaccharide whose -OH on the penultimate carbon is on the left in a Fischer projection called?

L-Monosaccharide

Which chiral center is used to determine D or L configuration?

Highest-numbered chiral center

For what purpose is the carbonyl group end used in Fischer projections?

Numbering the carbon chain

In Fischer projections, what do vertical lines represent?

Lines representing bonds directed into the printed page

In Fischer projections, what do horizontal lines represent?

Lines representing bonds directed out of the printed page

What geometry is assumed by the four groups attached to a chiral center?

Tetrahedral geometry

What type of isomers differ in most chemical and physical properties?

Constitutional isomers

What property of enantiomers involves the rotation of plane-polarized light?

Optical isomerism

What instrument is used to determine + and – rotation?

Polarimeter

What is a chiral compound that rotates plane-polarized light to the right (+) called?

Dextrorotatory

What is a chiral compound that rotates plane-polarized light to the left (–) called?

Levorotatory

What type of light moves in all directions?

Ordinary light

What type of light moves only in one direction?

Plane-polarized light

What is the ability of compounds to rotate plane-polarized light called?

Optical activity

In what type of solvent do enantiomers have the same solubility?

Achiral solvent

In what type of solvent do enantiomers have different solubility?

Chiral solvent

What chiral compound is found in spearmint leaves?

L-Carvone

What chiral compound is found in caraway seeds?

D-Carvone

What characteristic is possessed by molecules whose mirror images are not superimposable?

Chirality

What are molecules called whose mirror images are superimposable?

Achiral

What handedness do most amino acids possess?

Left-handed

What handedness do most monosaccharides possess?

Right-handed

What is a monosaccharide containing 3 carbon atoms called?

Triose

What is a monosaccharide containing 4 carbon atoms called?

Tetrose

What is a monosaccharide containing 5 carbon atoms called?

Pentose

What is a monosaccharide containing 6 carbon atoms called?

Hexose

What are monosaccharides with one aldehyde group called?

Aldoses

What are monosaccharides with one ketone group called?

Ketoses

What is a monosaccharide with an aldehyde group and 6 carbon atoms called?

Aldohexose

What is a monosaccharide with a ketone group and 6 carbon atoms called?

Ketohexose

What is the most abundant monosaccharide in nature?

Glucose

What is the sweetest tasting of all sugars?

Fructose

What monosaccharide is also called grape sugar, dextrose, and blood sugar?

Glucose

What ketohexose is commonly found in fruits and honey?

Fructose

What monosaccharide is known as milk sugar?

Galactose

What monosaccharide is also called brain sugar?

Galactose

Which monosaccharide is part of RNA?

Ribose

Which monosaccharide is part of ATP?

Ribose

What hospital IV solution is commonly used as a source of nourishment?

5% glucose solution

Which aldohexose is used to differentiate blood types?

Galactose

Which monosaccharide with a six-membered cyclic form is nutritionally most important?

Glucose

What reaction occurs when a hemiacetal reacts with a second alcohol molecule?

Acetal formation

What type of reaction is involved in acetal formation?

Condensation reaction

What is the dominant form of monosaccharides with five or more carbon atoms?

Cyclic form

What form exists in equilibrium with the cyclic form of monosaccharides?

Open-chain form

Which functional group reacts with the hydroxyl group to form cyclic glucose?

Carbonyl group

On which carbon number is the hydroxyl group involved in the cyclization of D-glucose found?

Carbon 5

What is the form of D-glucose where the -OH of C1 and CH2OH of C5 are on opposite sides?

Alpha form

What is the form of D-glucose where the -OH of C1 and CH2OH of C5 are on the same side?

Beta form

What is a cyclic monosaccharide containing a six-atom ring called?

Pyranose

What is a cyclic monosaccharide containing a five-atom ring called?

Furanose

Which ring structure resembles pyran?

Pyranose

Which ring structure resembles furan?

Furanose