Exam 5: Stereochemistry at Tetrahedral Centers

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Exhibit 5-7 A natural product having [α]_D = +40.3° has been isolated and purified. -Refer to Exhibit 5-7.Two structures have been proposed for this natural product.Circle the structure that is consistent with the information presented and briefly explain your choice.

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Question 1

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The information presented indicates that the natural product is optically active.To be optically active molecules must be chiral-that is,they must not have a plane of symmetry.The cyclic structure,although has chirality centers,has a plane of symmetry,indicated by the dashed line on the structure,and can,therefore,not be optically active.The circled structure has four chirality centers,and is not symmetric.We would expect it to be optically active.

Exhibit 5-5 Label each pair of stereoisomers below as: -_____

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Question 2

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Exhibit 5-6 Refer to the structure below to answer the following question(s). -Refer to Exhibit 5-6.Draw the enantiomer of (S)-(−)-serine in a wedge-dash projection.

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Question 3

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A white solid known to be enantiomerically pure is dissolved in water.This solution produced an observed optical rotation of +45.6°.The solution was allowed to stand and the optical rotation was measured repeatedly producing the data shown in the table. Explain the pattern of observed rotation.

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Question 4

In muscles during strenuous exercise,under anaerobic conditions lactic acid builds up due to the following reaction. The carbon atom indicated by the asterisk is

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Question 5

For which of the following generic substances is it not possible to isolate the enantiomers? (R₁,R₂ and R₃ represent different groups. )

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Question 6

Exhibit 5-5 Label each pair of stereoisomers below as: -_____

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Question 7

_____ is an sp³-hybridized atom that can become a chirality center by changing one of its attached groups.

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Question 8

Exhibit 5-5 Label each pair of stereoisomers below as: -_____

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Question 9

____ are organic molecules which rotate the plane of polarization of plane-polarized light.

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Question 10

_____ is the reason for "handedness" in molecules;the property of an object that causes it to be nonsuperimposable on its mirror image.

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Question 11

Exhibit 5-5 Label each pair of stereoisomers below as: -_____

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Question 12

Exhibit 5-3 Assign R,S configurations to each indicated chirality center in the molecules below. -Refer to Exhibit 5-3.The configuration of this carbon atom (E) is _____.

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Question 13

_____ are molecules which contain a plane of symmetry and chirality centers,but are achiral.

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Question 14

Exhibit 5-4 Consider the structure of streptimidone to answer the following question(s). -Refer to Exhibit 5-4.Assign R or S configuration to each chirality center indicated in streptimidone.

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Question 15

(2R,3S)-Dibromobutane is:

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Question 16

Exhibit 5-4 Consider the structure of streptimidone to answer the following question(s). -Refer to Exhibit 5-4.Will streptimidone have a meso stereoisomer? Explain your answer.

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Question 17

Explain why a work glove is chiral but disposable surgical gloves are not.

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Question 18

Which of the following would be has the highest priority according to the sequence rules?

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Question 19

Which of the following arranges the groups in order of decreasing priority according to the sequence rules?

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Question 20

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Exam 5: Stereochemistry at Tetrahedral Centers

Exhibit 5-7 A natural product having [α]D = +40.3° has been isolated and purified. -Refer to Exhibit 5-7.Two structures have been proposed for this natural product.Circle the structure that is consistent with the information presented and briefly explain your choice. ​

Exhibit 5-5 Label each pair of stereoisomers below as: -_____

Exhibit 5-6 Refer to the structure below to answer the following question(s). ​ -Refer to Exhibit 5-6.Draw the enantiomer of (S)-(−)-serine in a wedge-dash projection.

A white solid known to be enantiomerically pure is dissolved in water.This solution produced an observed optical rotation of +45.6°.The solution was allowed to stand and the optical rotation was measured repeatedly producing the data shown in the table. Explain the pattern of observed rotation.

In muscles during strenuous exercise,under anaerobic conditions lactic acid builds up due to the following reaction. The carbon atom indicated by the asterisk is

For which of the following generic substances is it not possible to isolate the enantiomers? (R1,R2 and R3 represent different groups. )

Exhibit 5-5 Label each pair of stereoisomers below as: -_____

_____ is an sp3-hybridized atom that can become a chirality center by changing one of its attached groups.

Exhibit 5-5 Label each pair of stereoisomers below as: -_____

____ are organic molecules which rotate the plane of polarization of plane-polarized light.

_____ is the reason for "handedness" in molecules;the property of an object that causes it to be nonsuperimposable on its mirror image.

Exhibit 5-5 Label each pair of stereoisomers below as: -_____

Exhibit 5-3 Assign R,S configurations to each indicated chirality center in the molecules below. ​ -Refer to Exhibit 5-3.The configuration of this carbon atom (E) is _____.

_____ are molecules which contain a plane of symmetry and chirality centers,but are achiral.

Exhibit 5-4 Consider the structure of streptimidone to answer the following question(s). ​ -Refer to Exhibit 5-4.Assign R or S configuration to each chirality center indicated in streptimidone.

(2R,3S)-Dibromobutane is:

Exhibit 5-4 Consider the structure of streptimidone to answer the following question(s). ​ -Refer to Exhibit 5-4.Will streptimidone have a meso stereoisomer? Explain your answer.

Explain why a work glove is chiral but disposable surgical gloves are not.

Which of the following would be has the highest priority according to the sequence rules?

Which of the following arranges the groups in order of decreasing priority according to the sequence rules?

Structure and Bonding

Polar Covalent Bonds;acids and Bases

Organic Compounds: Alkanes and Their Stereochemistry

Organic Compounds: Cycloalkanes and Their Stereochemistry

An Overview of Organic Reactions

Par 1

Alkenes: Structure and Reactivity

Alkenes: Reactions and Synthesis

Alkynes: an Introduction to Organic Synthesis

Organohalides

Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations

Par 2

Structure Determination: Mass Spectrometry and Infrared Spectroscopy

Structure Determination: Nuclear Magnetic Resonance Spectroscopy

Conjugated Compounds and Ultraviolet Spectroscopy

Par 3

Benzene and Aromaticity

Chemistry of Benzene: Electrophilic Aromatic Substitution

Alcohols and Phenols

Ethers and Epoxides;thiols and Sulfides

Aldehydes and Ketones: Nucleophilic Addition Reactions

Par 4

Carboxylic Acids and Nitriles

Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions

Carbonyl Alpha-Substitution Reactions

Carbonyl Condensation Reactions

Par 5

Amines and Heterocycles

Biomolecules: Carbohydrates

Biomolecules: Amino Acids,peptides,and Proteins

Par 7

Biomolecules: Lipids

Biomolecules: Nucleic Acids

The Organic Chemistry of Metabolic Pathways

Orbitals and Organic Chemistry: Pericyclic Reactions

Synthetic Polymers

Par 1

Filters

Exhibit 5-7 A natural product having [α]_D = +40.3° has been isolated and purified. -Refer to Exhibit 5-7.Two structures have been proposed for this natural product.Circle the structure that is consistent with the information presented and briefly explain your choice.

Exhibit 5-6 Refer to the structure below to answer the following question(s). -Refer to Exhibit 5-6.Draw the enantiomer of (S)-(−)-serine in a wedge-dash projection.

For which of the following generic substances is it not possible to isolate the enantiomers? (R₁,R₂ and R₃ represent different groups. )

_____ is an sp³-hybridized atom that can become a chirality center by changing one of its attached groups.

Exhibit 5-3 Assign R,S configurations to each indicated chirality center in the molecules below. -Refer to Exhibit 5-3.The configuration of this carbon atom (E) is _____.

Exhibit 5-4 Consider the structure of streptimidone to answer the following question(s). -Refer to Exhibit 5-4.Assign R or S configuration to each chirality center indicated in streptimidone.

Exhibit 5-4 Consider the structure of streptimidone to answer the following question(s). -Refer to Exhibit 5-4.Will streptimidone have a meso stereoisomer? Explain your answer.