Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

5. Chirality

Constitutional Isomers vs. Stereoisomers

Organic Chemistry

5. Chirality

Constitutional Isomers vs. Stereoisomers

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7:25 minutes

Problem 5

Textbook Question

Draw a three-dimensional structure for each compound, and star all asymmetric carbon atoms. Draw the mirror image for each structure, and state whether you have drawn a pair of enantiomers or just the same molecule twice.Build molecular models of any of these examples that seem difficult to youe. Chlorocyclohexanef. Cis-1,2-dichlorocyclobutane

Verified step by step guidance

**Step 1:** Start by drawing the basic cyclohexane and cyclobutane rings. For chlorocyclohexane, draw a hexagonal ring, and for cis-1,2-dichlorocyclobutane, draw a square ring.

**Step 2:** For chlorocyclohexane, add a chlorine atom to one of the carbon atoms in the cyclohexane ring. Consider the chair conformation to visualize the 3D structure, and place the chlorine atom in either an axial or equatorial position.

**Step 3:** For cis-1,2-dichlorocyclobutane, add chlorine atoms to the 1st and 2nd carbon atoms of the cyclobutane ring. Ensure both chlorine atoms are on the same side of the ring to maintain the 'cis' configuration.

**Step 4:** Identify asymmetric carbon atoms. In chlorocyclohexane, check if the carbon with the chlorine atom is asymmetric by seeing if it is bonded to four different groups. In cis-1,2-dichlorocyclobutane, check each carbon atom for asymmetry.

**Step 5:** Draw the mirror image of each compound. For chlorocyclohexane, reflect the entire structure, including the position of the chlorine atom. For cis-1,2-dichlorocyclobutane, reflect the positions of the chlorine atoms. Determine if the mirror images are non-superimposable (enantiomers) or superimposable (identical molecules).

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Key Concepts

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

Asymmetric Carbon Atoms

Asymmetric carbon atoms, or chiral centers, are carbon atoms that are bonded to four different substituents. This unique arrangement allows for the existence of stereoisomers, specifically enantiomers, which are non-superimposable mirror images of each other. Identifying these centers is crucial for understanding the chirality of a molecule and its potential optical activity.

Enantiomers

Enantiomers are a type of stereoisomer that are mirror images of each other and cannot be superimposed. They typically have identical physical properties except for their interaction with plane-polarized light and reactions in chiral environments. Recognizing whether two structures represent enantiomers is essential for understanding their chemical behavior and biological activity.

Cyclic Compounds and Stereochemistry

Cyclic compounds, such as chlorocyclohexane and cis-1,2-dichlorocyclobutane, have unique stereochemical properties due to their ring structure. The arrangement of substituents around the ring can lead to different stereoisomers, including cis and trans configurations. Understanding the three-dimensional arrangement of atoms in these compounds is vital for accurately drawing their structures and determining their stereochemical relationships.

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Related Practice

Textbook Question

Which of the following compounds are capable of being resolved into enantiomers?

(a) N-ethyl-N-methylaniline

(b) 2-methylpiperidine

Textbook Question

For each of the following molecules, identify all stereocenters and draw all possible stereoisomers.

(a)

Textbook Question

For each of the following molecules, identify all stereocenters and draw all possible stereoisomers.

(f)

Textbook Question

For each of the following molecules, identify all stereocenters and draw all possible stereoisomers.

(b)

Textbook Question

Draw a three-dimensional structure for each compound, and star all asymmetric carbon atoms. Draw the mirror for each structure, and state whether you have drawn a pair of enantiomers or just the same molecule twice. Build molecular models of any of these examples that seem difficult to you.

(e) chlorocyclohexane

(f) cis-1,2-dichlorocyclobutane

Textbook Question

For each pair, give the relationship between the two compounds. Making models will be helpful.

(a) (2R,3S)-2,3-dibromohexane and (2S,3R)-2,3-dibromohexane

(b) (2R,3S)-2,3-dibromohexane and (2R,3R)-2,3-dibromohexane

Textbook Question

For the compound 1-ethyl-3-isopropylcyclopentane,

(b) What is the stereochemical relationship between the cis isomers?

Textbook Question

(a) Give the products expected when (+)@glyceraldehyde reacts with HCN.(b) What is the relationship between the products? How might they be separated?(c) Are the products optically active? Explain.

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