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Ch.4 Introduction to Organic Compounds
Frost - General, Organic and Biological Chemistry 4th Edition
Frost4th EditionGeneral, Organic and Biological ChemistryISBN: 9780134988696Not the one you use?Change textbook
All textbooksFrost 4th EditionCh.4 Introduction to Organic CompoundsProblem 82c
Chapter 1, Problem 82c

Draw the enantiomer of each of the following compounds. If the compound is not chiral, state that fact.
(c) Chemical structure of a pentagon with an -OH group attached, indicating a non-chiral compound.

Verified step by step guidance
1
Analyze the given structure: The compound is a cyclopentane ring with a hydroxyl (-OH) group attached via a wedge bond, indicating stereochemistry.
Determine chirality: A compound is chiral if it has a carbon atom bonded to four different groups and lacks a plane of symmetry. In this case, the carbon attached to the -OH group is bonded to two identical groups (two hydrogens), making the compound achiral.
State the conclusion: Since the compound is not chiral, it does not have an enantiomer.
Explain why enantiomers cannot exist: Enantiomers are non-superimposable mirror images of chiral molecules. Because this molecule is achiral, it cannot have a non-superimposable mirror image.
Summarize: The compound is achiral, and no enantiomer can be drawn for this structure.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Chirality

Chirality refers to the geometric property of a molecule that makes it non-superimposable on its mirror image. A chiral molecule typically has four different substituents attached to a central carbon atom, creating two distinct forms known as enantiomers. Understanding chirality is crucial for determining whether a compound can exist in multiple forms that differ in spatial arrangement.
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Enantiomers

Enantiomers are a pair of molecules that are mirror images of each other but cannot be superimposed. They often exhibit different optical activities, meaning they rotate plane-polarized light in opposite directions. Identifying enantiomers is essential in organic chemistry, especially in the context of pharmaceuticals, where different enantiomers can have vastly different biological effects.
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Chiral Centers

A chiral center, often a carbon atom, is a point in a molecule where four different groups are attached, leading to chirality. If a molecule lacks a chiral center, it is considered achiral and does not have enantiomers. In the provided compound, the absence of a chiral center indicates that it is not chiral, and thus, no enantiomer can be drawn.
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Related Practice
Textbook Question

Mark the chiral centers in the following molecules, if any, with an asterisk (*).

(d)

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Textbook Question

Mark the chiral centers in the following molecules, if any, with an asterisk (*).

(d)

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Textbook Question

Are the following compounds structural isomers, cis–trans isomers, or enantiomers?

(c) 

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Textbook Question

Certain omega-3 fatty acids can be found only in animal sources, such as fatty fish. Two of these are eicosapentaenoic acid (EPA) [20:5] and docosahexaenoic acid (DHA) [22:6], both of which are ω-3 fatty acids. DHA has been shown to be important in healthy brain development, so it has recently been added to infant formulas. Breast milk is rich in DHA as long as the mother maintains a healthy diet that includes fish. Draw skeletal structures of the fatty acids EPA and DHA.

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Textbook Question

For each pair of molecules, identify the pair as:

A. structural isomers.

B. the same molecule (conformational isomers).

C. cis–trans stereoisomers.

D. different molecules.                                                                                                                                                                 

(b)

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