Organic Chemistry (CHM 221) Chapter 5.1
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Questions and Answers

What is the meaning of stereochemistry?

Stereochemistry deals with the three-dimensional structure of a molecule and how minor differences in structure can lead to vastly different properties.

What is the difference between glucose and galactose in terms of stereochemistry?

Glucose and galactose are isomers, meaning they have the same molecular formula but differ in the spatial arrangement of their atoms. The difference lies in the orientation of the hydroxyl group at the position of carbon 4.

Explain the difference between cellulose and starch in terms of stereochemistry.

The difference between cellulose and starch lies in the orientation of the oxygen atom that joins two sugar rings. Cellulose has two equatorial bonds, while starch has one equatorial and one axial bond. This difference in stereochemistry makes cellulose indigestible by humans, whereas starch is a source of energy.

A chiral molecule is superimposable on its mirror image.

<p>False (B)</p> Signup and view all the answers

What are enantiomers?

<p>Enantiomers are a type of stereoisomers that are non-superimposable mirror images of each other. They have the same molecular formula, but differ in their three-dimensional structure and thus, have distinct properties.</p> Signup and view all the answers

Describe the importance of understanding enantiomers in drug development?

<p>Understanding enantiomers is crucial in drug development because different enantiomers of a drug can have different effects on the body. One enantiomer may be effective in treating a disease while its mirror image may be ineffective or even toxic.</p> Signup and view all the answers

What is a stereogenic center?

<p>A stereogenic center is an atom in a molecule, often a carbon atom, that is bonded to four different groups. The presence of a stereogenic center can lead to chiral molecules.</p> Signup and view all the answers

Flashcards

Stereochemistry

The study of the 3-dimensional structure of molecules and how it impacts their properties.

Isomers

Compounds with the same molecular formula but different arrangements of atoms.

Stereoisomers

Isomers that have the same connectivity of atoms but different spatial arrangements.

Constitutional Isomers

Isomers that differ in the way atoms are connected.

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Achiral

A molecule or object that can be superimposed on its mirror image.

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Chiral

A molecule or object that cannot be superimposed on its mirror image.

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Stereogenic Center

A specific point in a molecule where four different groups are attached to a central atom, usually carbon.

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Plane of Symmetry

A mirror plane that divides a molecule into two identical halves.

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Enantiomers

Nonsuperimposable mirror images of a molecule.

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Tetrahedral Stereogenic Center

A chiral carbon atom with four different groups attached.

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Enantiomeric Excess

The difference in physical and chemical properties between enantiomers caused by their different interactions with other chiral molecules.

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Racemic Mixture

A mixture of equal amounts of two enantiomers.

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Meso Compound

A molecule with two or more chiral centers, but the molecule itself is achiral due to an internal plane of symmetry.

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Epimerization

The conversion of one enantiomer into another.

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Resolution

The process of separating a racemic mixture into its individual enantiomers.

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Non-Stereogenic Center

A carbon atom with two or more identical groups attached.

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Optical Activity

The study of how molecules interact with polarized light.

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Dextrorotatory

A molecule that rotates plane-polarized light to the right.

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Levorotatory

A molecule that rotates plane-polarized light to the left.

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Optical Rotation

A measure of the amount of rotation of plane-polarized light by a chiral molecule.

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Optically Inactive

A molecule that does not rotate plane-polarized light.

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Chiral Resolution

The ability of an achiral molecule to become chiral by reacting with a chiral reagent.

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Stereochemistry in Biology

The study of stereochemistry and its effect on the biological activity of molecules.

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Chiral Recognition

The ability of a chiral molecule to recognize and bind to another molecule based on its specific chirality.

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Diastereomers

A molecule with two or more stereogenic centers where changing the configuration at one center also changes the configuration at another center.

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Epimer

A stereocenter whose configuration can be changed without breaking any covalent bonds.

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Syn Diastereomers

A molecule with two or more stereogenic centers that have the same configuration.

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Anti Diastereomers

A molecule with two or more stereogenic centers that have opposite configurations.

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Diastereoselective Synthesis

The process of converting a molecule with one stereogenic center into a molecule with two or more stereogenic centers.

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Stereoselectivity

The ability of a reagent or catalyst to selectively direct the formation of one stereoisomer over another.

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Study Notes

Organic Chem Chapter 5 Part 1

  • This chapter focuses on the orientation of molecules and how their 3-D structure affects reactions.
  • Specific products can have similar appearances but differ in the position of atoms or functional groups when their bonding orientations are compared.
  • The chapter primarily emphasizes concepts rather than chemical reactions.
  • The chapter is divided into two parts to allow homework assignments to be completed.

Stereochemistry

  • Stereochemistry investigates the 3-D structure of molecules.
  • Subtle differences in molecular shape can lead to significant variations in properties.
  • Examples include glucose and galactose, which have differing melting points and sweetness despite similar formulas.

Stereochemistry of Starch and Cellulose

  • Cellulose utilizes equatorial bonds to link rings, while starch uses one equatorial and one axial bond.
  • This difference in bonding leads to humans being able to metabolize starch for energy but not digest cellulose.

3-D Structure of Starch and Cellulose

  • Cellulose forms a vast 3-dimensional network stabilized by hydrogen bonds.
  • Starch polymers form a helix-like structure.

Isomers

  • Isomers are different compounds with the same molecular formula.
  • Two main categories are constitutional isomers and stereoisomers.
  • Constitutional isomers have different IUPAC names and different physical and chemical properties despite identical molecular formulas.
  • Stereoisomers have identical IUPAC names (except for prefixes like cis or trans), identical functional groups, but different 3-D arrangements leading to potential differences in properties.

Constitutional and Stereoisomers

  • Examples provided include 2-methylpentane and 3-methylpentane as constitutional isomers.
  • Cis-1,2-dimethylcyclopentane and trans-1,2-dimethylcyclopentane are stereoisomers of the same molecular formula.

Superimposable (Achiral) Objects

  • Objects superimposable on their mirror image are called achiral.
  • A pair of socks are an example of two superimposable mirror images.
  • Molecules that can be exactly overlaid on their mirror images are achiral.

Achiral Molecules

  • Examples like H₂O and CH₂BrCl are given as achiral molecules whose bonds and atoms align when superimposing mirror images.

Nonsuperimposable Mirror Images

  • A molecule is chiral if it is not superimposable on its mirror image.
  • Chiral molecules are asymmetrical, with no plane of symmetry.
  • Hands are a common example of nonsuperimposable mirror images.

Example of Nonsuperimposable Mirror Images

  • Hands are mirror images and not superimposable.

Stereogenic Centers

  • A stereogenic center is a point in a molecule where the interchange of substituents creates a stereoisomer.
  • This is not always an atom, but could be any point in the molecule.
  • Identifying tetrahedral carbon atoms that have four different groups attached is key to finding stereogenic centers.
  • Groups like CH₂ and CH₃, and sp or sp² hybridized carbons are not considered stereogenic centers.

Multiple Stereogenic Centers

  • Large organic molecules can have multiple stereogenic centers.
  • Examples include propoxyphene (an analgesic), ephedrine, and fructose.

Is This Molecule Chiral?

  • Rotation can provide a planar symmetry in some cases, making a molecule achiral.

Enantiomers

  • Enantiomers are non-superimposable mirror image molecules.
  • Any molecule with one stereogenic center exists as a pair of enantiomers.
  • An example is the different structures of 2-butanol enantiomers.

Importance of Understanding Enantiomers

  • One enantiomer can have beneficial effects while the other is detrimental or even toxic.
  • The example of naproxen and liver toxicity is used.

Drawing Enantiomers

  • Enantiomers are drawn by first arbitrarily placing the groups around a stereogenic center and then reflecting the molecule to produce the mirror image.

Summary of Chirality

  • The fundamental question about chirality is whether a molecule and its mirror image are superimposable.
  • If not, the molecule is chiral and no plane of symmetry is present.
  • Enantiomers are a pair of molecules that aren't superimposable but are mirror images.
  • Stereogenic centers are critical to determining chirality.

Homework Assignments for this Chapter

  • The homework problems focus on 5.2 (pg 182), 5.3, 5.6 (a, b, c), 5.9 (a, b), and problems related to molecules getting larger like 5.8.
  • Problem 5.2(further details on pg 188) should be studied in detail.
  • Other assigned end-of-chapter problems include 5.41 (a & b), 5.42 (a & b), and 5.43.

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This quiz covers the concepts of stereochemistry in Organic Chemistry Chapter 5, focusing on the 3-D structures of molecules and their implications in chemical reactions. You'll explore how differences in atomic orientation affect properties and functions of compounds like glucose and cellulose. Dive into the nuances of molecular shape and its importance in chemistry.

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