The way in which four stereoisomers arise for 3-penten-2-ol has to be explained. Concept Introduction: Alkene: Unsaturated hydrocarbons having at least one double bond between two carbon atoms are known as alkenes . Geometric isomers: Two compounds are considered as geometric isomers of each other if both contain same number of atoms but different in their arrangement. E configuration: The geometric isomers are given E configuration if high priority groups are placed on opposite sides of the double bond. Z configuration: The geometric isomers are given Z configuration if high priority groups are placed on same sides of the double bond. Chirality: It refers to a Carbon atom in a molecule that contains four different substituents. According to Cahn-Ingold-Prelog system, The group attached to asymmetric center should be ranked based on the atomic number of atom which directly connected to asymmetric center. The higher the atomic number of atom, higher the priority. If there is tie, then consider the next atoms attached to the connected atom and so on. Check the direction of arrow drawn in the direction of decreasing priority. If the arrow points clockwise direction, then the atom has R configuration. If the arrow points counterclockwise direction, then the atom has S configuration. If the group with lowest priority is not bonded by a hatched wedge, then interchange this group (lowest priority) by group bonded to hatched wedge and draw the arrow in priority order but the configuration is assigned as just reverse.

Question

For cis-1,3-diethylcyciobutane, draw (a) a stereoisomer; (b) a constitutional isomer.

Answer 1

Question

Definition Definition Molecules that have multiple bonds between their carbon atoms. Alkenes are hydrocarbons with a double bond between two adjacent carbon atoms (R 2 C=CR 2 ), whereas alkynes are hydrocarbons with a triple bond between two adjacent carbon atoms R-C=C-R . These two groups are known as unsaturated hydrocarbons. They have fewer hydrogen atoms when compared with alkanes with same number of carbon atoms. The general molecular formula for an unsaturated hydrocarbon can be represented as C n H 2n +2 .

Chapter 5, Problem 5.24P

(a)

Interpretation Introduction

Interpretation:

The way in which four stereoisomers arise for 3-penten-2-ol has to be explained.

Concept Introduction:

Alkene: Unsaturated hydrocarbons having at least one double bond between two carbon atoms are known as alkenes.

Geometric isomers: Two compounds are considered as geometric isomers of each other if both contain same number of atoms but different in their arrangement.

E configuration: The geometric isomers are given E configuration if high priority groups are placed on opposite sides of the double bond.

Z configuration: The geometric isomers are given Z configuration if high priority groups are placed on same sides of the double bond.

Chirality: It refers to a Carbon atom in a molecule that contains four different substituents.

According to Cahn-Ingold-Prelog system,

The group attached to asymmetric center should be ranked based on the atomic number of atom which directly connected to asymmetric center. The higher the atomic number of atom, higher the priority. If there is tie, then consider the next atoms attached to the connected atom and so on.

Check the direction of arrow drawn in the direction of decreasing priority. If the arrow points clockwise direction, then the atom has R configuration. If the arrow points counterclockwise direction, then the atom has S configuration. If the group with lowest priority is not bonded by a hatched wedge, then interchange this group (lowest priority) by group bonded to hatched wedge and draw the arrow in priority order but the configuration is assigned as just reverse.

(a)

Interpretation Introduction

Interpretation:

The stereoisomer having the E configuration at the carbon-carbon double bond and the R configuration at the chiral center has to be drawn.

Concept Introduction:

Alkene: Unsaturated hydrocarbons having at least one double bond between two carbon atoms are known as alkenes.

Geometric isomers: Two compounds are considered as geometric isomers of each other if both contain same number of atoms but different in their arrangement.

E configuration: The geometric isomers are given E configuration if high priority groups are placed on opposite sides of the double bond.

Z configuration: The geometric isomers are given Z configuration if high priority groups are placed on same sides of the double bond.

Chirality: It refers to a Carbon atom in a molecule that contains four different substituents.

According to Cahn-Ingold-Prelog system,

The group attached to asymmetric center should be ranked based on the atomic number of atom which directly connected to asymmetric center. The higher the atomic number of atom, higher the priority. If there is tie, then consider the next atoms attached to the connected atom and so on.

Check the direction of arrow drawn in the direction of decreasing priority. If the arrow points clockwise direction, then the atom has R configuration. If the arrow points counterclockwise direction, then the atom has S configuration. If the group with lowest priority is not bonded by a hatched wedge, then interchange this group (lowest priority) by group bonded to hatched wedge and draw the arrow in priority order but the configuration is assigned as just reverse.

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For cis-1,3-diethylcyciobutane, draw (a) a stereoisomer; (b) a constitutional isomer.

Draw the structures for the following compounds.(a) 3-benzyl-4-bromohexane , 4,4-dimethylcyclohexene(b) trans-4,5-dibromohex-2-ene , cis-1,1-dibromo-2-ethyl-2,3-dimethylcyclobutane

(a) Draw a skeletal structure of the anabolic steroid 4-androstene-3,17-dione, also called "andro," from the following description. Andro contains the tetracyclic steroid skeieton with carbonyl groups at C3 and C17, a double bond between C4 and C5, and methyl groups bonded to C10 and C13. (b) Add wedges and dashes for all stereogenic centers with the following information: the configuration at C10 is R, the configuration at C13 is S, and all substituents at ring fusions are trans to each other.

Answer 2

Question

Definition Definition Molecules that have multiple bonds between their carbon atoms. Alkenes are hydrocarbons with a double bond between two adjacent carbon atoms (R 2 C=CR 2 ), whereas alkynes are hydrocarbons with a triple bond between two adjacent carbon atoms R-C=C-R . These two groups are known as unsaturated hydrocarbons. They have fewer hydrogen atoms when compared with alkanes with same number of carbon atoms. The general molecular formula for an unsaturated hydrocarbon can be represented as C n H 2n +2 .

Chapter 5, Problem 5.24P

(a)

Interpretation Introduction

Interpretation:

The way in which four stereoisomers arise for 3-penten-2-ol has to be explained.

Concept Introduction:

Alkene: Unsaturated hydrocarbons having at least one double bond between two carbon atoms are known as alkenes.

Geometric isomers: Two compounds are considered as geometric isomers of each other if both contain same number of atoms but different in their arrangement.

E configuration: The geometric isomers are given E configuration if high priority groups are placed on opposite sides of the double bond.

Z configuration: The geometric isomers are given Z configuration if high priority groups are placed on same sides of the double bond.

Chirality: It refers to a Carbon atom in a molecule that contains four different substituents.

According to Cahn-Ingold-Prelog system,

The group attached to asymmetric center should be ranked based on the atomic number of atom which directly connected to asymmetric center. The higher the atomic number of atom, higher the priority. If there is tie, then consider the next atoms attached to the connected atom and so on.

Check the direction of arrow drawn in the direction of decreasing priority. If the arrow points clockwise direction, then the atom has R configuration. If the arrow points counterclockwise direction, then the atom has S configuration. If the group with lowest priority is not bonded by a hatched wedge, then interchange this group (lowest priority) by group bonded to hatched wedge and draw the arrow in priority order but the configuration is assigned as just reverse.

(a)

Interpretation Introduction

Interpretation:

The stereoisomer having the E configuration at the carbon-carbon double bond and the R configuration at the chiral center has to be drawn.

Concept Introduction:

Alkene: Unsaturated hydrocarbons having at least one double bond between two carbon atoms are known as alkenes.

Geometric isomers: Two compounds are considered as geometric isomers of each other if both contain same number of atoms but different in their arrangement.

E configuration: The geometric isomers are given E configuration if high priority groups are placed on opposite sides of the double bond.

Z configuration: The geometric isomers are given Z configuration if high priority groups are placed on same sides of the double bond.

Chirality: It refers to a Carbon atom in a molecule that contains four different substituents.

According to Cahn-Ingold-Prelog system,

The group attached to asymmetric center should be ranked based on the atomic number of atom which directly connected to asymmetric center. The higher the atomic number of atom, higher the priority. If there is tie, then consider the next atoms attached to the connected atom and so on.

Check the direction of arrow drawn in the direction of decreasing priority. If the arrow points clockwise direction, then the atom has R configuration. If the arrow points counterclockwise direction, then the atom has S configuration. If the group with lowest priority is not bonded by a hatched wedge, then interchange this group (lowest priority) by group bonded to hatched wedge and draw the arrow in priority order but the configuration is assigned as just reverse.

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Answer 3

Question

Definition Definition Molecules that have multiple bonds between their carbon atoms. Alkenes are hydrocarbons with a double bond between two adjacent carbon atoms (R 2 C=CR 2 ), whereas alkynes are hydrocarbons with a triple bond between two adjacent carbon atoms R-C=C-R . These two groups are known as unsaturated hydrocarbons. They have fewer hydrogen atoms when compared with alkanes with same number of carbon atoms. The general molecular formula for an unsaturated hydrocarbon can be represented as C n H 2n +2 .

Chapter 5, Problem 5.24P

(a)

Interpretation Introduction

Interpretation:

The way in which four stereoisomers arise for 3-penten-2-ol has to be explained.

Concept Introduction:

Alkene: Unsaturated hydrocarbons having at least one double bond between two carbon atoms are known as alkenes.

Geometric isomers: Two compounds are considered as geometric isomers of each other if both contain same number of atoms but different in their arrangement.

E configuration: The geometric isomers are given E configuration if high priority groups are placed on opposite sides of the double bond.

Z configuration: The geometric isomers are given Z configuration if high priority groups are placed on same sides of the double bond.

Chirality: It refers to a Carbon atom in a molecule that contains four different substituents.

According to Cahn-Ingold-Prelog system,

The group attached to asymmetric center should be ranked based on the atomic number of atom which directly connected to asymmetric center. The higher the atomic number of atom, higher the priority. If there is tie, then consider the next atoms attached to the connected atom and so on.

Check the direction of arrow drawn in the direction of decreasing priority. If the arrow points clockwise direction, then the atom has R configuration. If the arrow points counterclockwise direction, then the atom has S configuration. If the group with lowest priority is not bonded by a hatched wedge, then interchange this group (lowest priority) by group bonded to hatched wedge and draw the arrow in priority order but the configuration is assigned as just reverse.

(a)

Interpretation Introduction

Interpretation:

The stereoisomer having the E configuration at the carbon-carbon double bond and the R configuration at the chiral center has to be drawn.

Concept Introduction:

Alkene: Unsaturated hydrocarbons having at least one double bond between two carbon atoms are known as alkenes.

Geometric isomers: Two compounds are considered as geometric isomers of each other if both contain same number of atoms but different in their arrangement.

E configuration: The geometric isomers are given E configuration if high priority groups are placed on opposite sides of the double bond.

Z configuration: The geometric isomers are given Z configuration if high priority groups are placed on same sides of the double bond.

Chirality: It refers to a Carbon atom in a molecule that contains four different substituents.

According to Cahn-Ingold-Prelog system,

The group attached to asymmetric center should be ranked based on the atomic number of atom which directly connected to asymmetric center. The higher the atomic number of atom, higher the priority. If there is tie, then consider the next atoms attached to the connected atom and so on.

Check the direction of arrow drawn in the direction of decreasing priority. If the arrow points clockwise direction, then the atom has R configuration. If the arrow points counterclockwise direction, then the atom has S configuration. If the group with lowest priority is not bonded by a hatched wedge, then interchange this group (lowest priority) by group bonded to hatched wedge and draw the arrow in priority order but the configuration is assigned as just reverse.

Expert Solution & Answer

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See solution

Check out sample textbook solution

Answer 4

Question

Definition Definition Molecules that have multiple bonds between their carbon atoms. Alkenes are hydrocarbons with a double bond between two adjacent carbon atoms (R 2 C=CR 2 ), whereas alkynes are hydrocarbons with a triple bond between two adjacent carbon atoms R-C=C-R . These two groups are known as unsaturated hydrocarbons. They have fewer hydrogen atoms when compared with alkanes with same number of carbon atoms. The general molecular formula for an unsaturated hydrocarbon can be represented as C n H 2n +2 .

Chapter 5, Problem 5.24P

(a)

Interpretation Introduction