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

4. Alkanes and Cycloalkanes

Cis vs Trans

Organic Chemistry

4. Alkanes and Cycloalkanes

Cis vs Trans

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5:27 minutes

Problem 34b

Textbook Question

Name the following cycloalkanes using the IUPAC system of nomenclature, being sure to indicate whether they are cis or trans.
(b)

Verified step by step guidance

Step 1: Identify the parent cycloalkane. Count the number of carbon atoms in the ring structure to determine the base name of the cycloalkane (e.g., cyclopentane, cyclohexane, etc.).

Step 2: Locate and identify substituents attached to the cycloalkane ring. Assign names to each substituent group (e.g., methyl, ethyl, etc.).

Step 3: Number the ring carbons to give the substituents the lowest possible numbers. Start numbering from the carbon that leads to the smallest set of locants for the substituents.

Step 4: Determine the stereochemistry (cis or trans) of the substituents. If the substituents are on the same side of the ring, the configuration is 'cis'; if they are on opposite sides, the configuration is 'trans.'

Step 5: Combine the information into the IUPAC name. Include the stereochemistry (cis or trans) at the beginning, followed by the substituents in alphabetical order with their locants, and finally the parent cycloalkane name.

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Key Concepts

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

Cycloalkanes

Cycloalkanes are saturated hydrocarbons that contain carbon atoms arranged in a ring structure. They follow the general formula CnH2n, where n is the number of carbon atoms. Understanding the structure of cycloalkanes is essential for naming them correctly, as their cyclic nature influences their chemical properties and nomenclature.

IUPAC Nomenclature

The International Union of Pure and Applied Chemistry (IUPAC) nomenclature provides a systematic method for naming chemical compounds. For cycloalkanes, the naming involves identifying the number of carbon atoms in the ring and using prefixes like 'cyclo-' followed by the appropriate alkane name. This standardized approach ensures clarity and consistency in chemical communication.

Cis-Trans Isomerism

Cis-trans isomerism is a form of stereoisomerism that occurs in cyclic compounds due to restricted rotation around the carbon-carbon bonds. In cycloalkanes, 'cis' indicates that substituents are on the same side of the ring, while 'trans' indicates they are on opposite sides. Recognizing these configurations is crucial for accurately naming and understanding the properties of cycloalkanes.

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Related Practice

Textbook Question

Which of the following compounds show cis-trans isomerism? Draw the cis and trans isomers of the ones that do.

(a) CH₃CH=CHCH₃

(b) CH₃C≡CCH₃

Textbook Question

Which of the following compounds show cis-trans isomerism? Draw the cis and trans isomers of those that do.

(a) CHF=CHF

(b) F₂C=CH₂

Textbook Question

Two compounds with the formula CH₃–CH=N–CH₃ are known.

b. What two compounds have this formula?

c. Explain why only one compound with the formula (CH₃)₂CNCH₃ is known.

Textbook Question

Which of the following structures represent the same compound? Which ones represent different compounds?

(b)

Textbook Question

Assign relative priorities to each set of substituents:

b. -CH₂CH₂OH, -OH, -CH₂Cl, -CH=CH₂

Textbook Question

Draw the Z isomer of an alkene that has a CH₃ and an H on one sp² carbon and isopropyl and butyl groups on the other sp² carbon.

Textbook Question

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Textbook Question

Assign relative priorities to each set of substituents:

a. -Br, -I, -OH, -CH₃

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Name the following cycloalkanes using the IUPAC system of nomenclature, being sure to indicate whether they are cis or trans. (b)

Key Concepts

Cycloalkanes

IUPAC Nomenclature

Cis-Trans Isomerism

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Name the following cycloalkanes using the IUPAC system of nomenclature, being sure to indicate whether they are cis or trans.
(b)