Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781337516402
Author: Brown
Publisher: Cengage
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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 each reaction below, decide if the first stable organic product that forms in solution will create a new CC bond, and check the appropriate box. Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below. Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first stable product you expect to form in solution. ? NH2 MgBr Will the first product that forms in this reaction create a new CC bond? ○ Yes ○ No MgBr ? Will the first product that forms in this reaction create a new CC bond? O Yes O No Click and drag to start drawing a structure. :☐ G x c olo Ar HE
Predicting As the lead product manager at OrganometALEKS Industries, you are trying to decide if the following reaction will make a molecule with a new C - C bond as its major product: H₂N O H 1. ? 2. H3O+ If this reaction will work, draw the major organic product or products you would expect in the drawing area below. If there's more than one major product, you can draw them in any arrangement you like. Be sure you use wedge and dash bonds if necessary, for example to distinguish between major products with different stereochemistry. 0 If the major products of this reaction won't have a new CC bond, just check the box under the drawing area and leave it blank. فا Explanation Check Click and drag to start drawing a structure.
Highlight the chirality (or stereogenic) center(s) in the given compound. A compound may have one or more stereogenic centers. OH OH OH OH OH OH
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