Organic Chemistry: Stereochemistry

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Questions and Answers

What is the term used to describe a molecule that is superimposable on its mirror image?

Chiral
Tetrahedral
Stereoisomer
Achiral (correct)

What is the term used to describe a carbon atom bonded to four different groups?

Tetrahedral center
Stereogenic center (correct)
Achiral center
Chiral center

What is the result of interchanging two groups on a tetrahedral stereogenic center?

It converts one enantiomer into another (correct)
It creates a plane of symmetry
It makes the molecule chiral
It makes the molecule achiral

What is the characteristic of a plane of symmetry in a molecule?

It divides the molecule into two identical halves (B) Signup and view all the answers

What is the term used to describe molecules that are isomers differing only in the three-dimensional arrangement of substituents?

Stereoisomers (A) Signup and view all the answers

What is the term used to describe mirror images that are not superimposable?

Enantiomers (D) Signup and view all the answers

What is the main focus of stereochemistry in organic chemistry?

Dealing with the structure of molecules in three dimensions (C) Signup and view all the answers

What is the main difference between constitutional isomers and stereoisomers?

The way their atoms are connected to each other (B) Signup and view all the answers

What is a characteristic of stereoisomers?

They have identical IUPAC names except for a prefix (D) Signup and view all the answers

What is a chiral molecule?

A molecule that is not superimposable on its mirror image (A) Signup and view all the answers

Which of the following is an example of an achiral molecule?

A sock (A) Signup and view all the answers

What is a common characteristic of constitutional isomers?

They have different IUPAC names (B) Signup and view all the answers

What is the purpose of the tube in a polarimeter?

To hold the substance being examined for optical activity (B) Signup and view all the answers

What happens when the substance does not affect the plane of polarization?

The light transmission is still at a maximum (D) Signup and view all the answers

What is a characteristic of a tetrahedral stereogenic center?

Being bonded to four different groups (D) Signup and view all the answers

What is the term for a substance that rotates the plane of polarization to the right?

Dextrorotatory (A) Signup and view all the answers

Which of the following molecules has a plane of symmetry?

CH2BrCl (C) Signup and view all the answers

What is the symbol used to indicate a rotation to the left?

<ul> <li>(D)</li> </ul> Signup and view all the answers

What is the minimum number of tetrahedral stereogenic centers required for a molecule to exist as a pair of enantiomers?

One (A) Signup and view all the answers

What is the arrangement of the lenses in a polarimeter when the tube is empty?

The lenses are arranged so that they pass light vibrating in the same plane (A) Signup and view all the answers

What type of carbon atoms should be omitted from consideration when looking for stereogenic centers?

sp or sp2 hybridized carbon atoms (D) Signup and view all the answers

What is the term for a substance that does not affect the plane of polarization?

Optically inactive (C) Signup and view all the answers

What is the correct way to depict a tetrahedron when drawing a pair of enantiomers?

Place two bonds in the plane, one in front of the plane on a wedge, and one behind the plane on a dash (C) Signup and view all the answers

Why is 3-methylcyclohexene a chiral compound?

Because it has a tetrahedral stereogenic center (C) Signup and view all the answers

Which of the following molecules can be chiral?

Molecules with no plane of symmetry (B) Signup and view all the answers

What is the minimum requirement for a molecule to be considered achiral?

The molecule has a plane of symmetry (C) Signup and view all the answers

What is the result of interchanging two groups on a carbon atom bonded to four different groups?

The molecule becomes a different enantiomer (D) Signup and view all the answers

What is the correct term for molecules that are isomers differing only in their three-dimensional arrangement of substituents?

Stereoisomers (D) Signup and view all the answers

Which of the following is NOT a characteristic of chiral molecules?

They are superimposable on their mirror image (B) Signup and view all the answers

What is the primary difference between chiral and achiral molecules?

The presence or absence of a plane of symmetry (A) Signup and view all the answers

What is the correct term for a molecule that has a non-superimposable mirror image?

Chiral molecule (D) Signup and view all the answers

Which type of isomers always have the same functional group(s)?

Stereoisomers (C) Signup and view all the answers

What is the characteristic of constitutional isomers that differs from stereoisomers?

Different functional groups (A) Signup and view all the answers

What is the relationship between the IUPAC names of stereoisomers?

They are identical except for a prefix (A) Signup and view all the answers

What is the characteristic of chiral molecules that is similar to hands?

They are not superimposable on their mirror images (D) Signup and view all the answers

What is the primary focus of stereochemistry in organic chemistry?

The structure of molecules in three dimensions (A) Signup and view all the answers

What is the primary purpose of the polarimeter?

To measure the optical activity of a substance (B) Signup and view all the answers

What happens to the plane of polarization when a substance is optically active?

It is rotated to the right or left (D) Signup and view all the answers

What is the significance of the maximum amount of light reaching our eye in a polarimeter?

It indicates the correct alignment of the lenses (A) Signup and view all the answers

Which carbon atom is bonded to four different groups in 3-methylcyclohexene?

C3 (D) Signup and view all the answers

What is the term used to describe a substance that rotates the plane of polarization to the right?

Dextrorotatory (C) Signup and view all the answers

What is the minimum number of tetrahedral stereogenic centers required for a molecule to exist as a pair of diastereomers?

2 (C) Signup and view all the answers

What is the arrangement of the lenses in a polarimeter when the tube is empty and a maximum amount of light reaches our eye?

The lenses pass light vibrating in the same plane (D) Signup and view all the answers

Why is it unnecessary to examine CH2 and CH3 groups when looking for stereogenic centers?

They can never be bonded to four different groups (A) Signup and view all the answers

What is the symbol used to indicate a rotation to the right in a polarimeter?

<ul> <li>(B)</li> </ul> Signup and view all the answers

What is the correct way to depict a tetrahedral stereogenic center when drawing a molecule?

Place two bonds in the plane, one in front of the plane on a wedge, and one behind the plane on a dash (D) Signup and view all the answers

What is the characteristic of a molecule with a plane of symmetry?

It is superimposable on its mirror image (B) Signup and view all the answers

What is the characteristic of a stereogenic center in a cyclic compound?

It must be bonded to four different groups (C) Signup and view all the answers

What is unique about a meso compound?

It has superimposable mirror images (C) Signup and view all the answers

Why is VII not chiral?

Because it has a plane of symmetry (C) Signup and view all the answers

What is a characteristic of a meso compound?

It always has a plane of symmetry (C) Signup and view all the answers

What happens when you interchange two groups on a tetrahedral stereogenic center?

The molecule becomes achiral (C) Signup and view all the answers

What is the relationship between VII and VIII?

They are superimposable (C) Signup and view all the answers

What is the result of making VIII, the mirror image of VII?

The two molecules are superimposable (C) Signup and view all the answers

What is a characteristic of a molecule with a plane of symmetry?

It is always achiral (A) Signup and view all the answers

What is the difference between VII and V/VI?

VII is a diastereomer of V and VI (D) Signup and view all the answers

Why is a meso compound optically inactive?

Because it has a plane of symmetry (B) Signup and view all the answers

What is the key characteristic of a meso compound in at least one of its conformations?

One half of the molecule is the mirror image of the other half (D) Signup and view all the answers

What is a characteristic of a meso compound?

It is optically inactive (D) Signup and view all the answers

What is the reason VII is not chiral?

It has a plane of symmetry (D) Signup and view all the answers

What is a characteristic of a stereogenic center?

It is a carbon atom bonded to four different groups (A) Signup and view all the answers

What is the relationship between VII and VIII?

They are superimposable (D) Signup and view all the answers

What is a characteristic of a molecule with a plane of symmetry?

It is achiral (C) Signup and view all the answers

What is the term used to describe a molecule that is superimposable on its mirror image?

Achiral molecule (A) Signup and view all the answers

What is unique about a meso compound compared to other stereoisomers?

It is optically inactive (B) Signup and view all the answers

What is the result of interchanging two groups on a tetrahedral stereogenic center?

The molecule becomes achiral (C) Signup and view all the answers

What is a characteristic of a diastereomer?

It is a type of stereoisomer (D) Signup and view all the answers

What is the term used to describe the process of recognizing a meso structure?

Symmetry recognition (D) Signup and view all the answers

What is the key characteristic of a meso compound?

It is superimposable on its mirror image. (A) Signup and view all the answers

Why is molecule VII not chiral?

Because it has a plane of symmetry. (C) Signup and view all the answers

What is the relationship between molecules V, VI, and VII?

They are diastereomers. (D) Signup and view all the answers

What is the condition for a molecule to be optically active?

It must have at least one stereogenic center. (D) Signup and view all the answers

What is the characteristic of a stereogenic center in a meso compound?

It has a plane of symmetry. (A) Signup and view all the answers

What is the result of interchanging two groups on a tetrahedral stereogenic center in a meso compound?

The molecule remains the same. (B) Signup and view all the answers

What is the key difference between a meso compound and a chiral molecule?

A meso compound has a plane of symmetry, while a chiral molecule does not. (D) Signup and view all the answers

What is the condition for a molecule to be a meso compound?

It must have a plane of symmetry. (C) Signup and view all the answers

What is the relationship between molecule VII and its mirror image?

They are superimposable. (B) Signup and view all the answers

What is the characteristic of a stereoisomer that is not a meso compound?

It is optically active. (A) Signup and view all the answers

Flashcards

Achiral

A molecule superimposable on its mirror image.

Stereogenic center

A carbon atom bonded to four different groups.