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

1. A Review of General Chemistry

Constitutional Isomers

Organic Chemistry

1. A Review of General Chemistry

Constitutional Isomers

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Problem 14a

Textbook Question

There are nine alkane constitutional isomers with the molecular formula C₇H₁₆. Draw them.

Verified step by step guidance

Step 1: Understand the concept of constitutional isomers. Constitutional isomers are compounds with the same molecular formula but different connectivity of atoms. For the molecular formula C₇H₁₆, we are tasked with finding all possible unique structures where the carbon and hydrogen atoms are connected differently.

Step 2: Start with the simplest structure, the straight-chain alkane. Draw n-heptane, which is a linear chain of seven carbon atoms (C-C-C-C-C-C-C) with the appropriate number of hydrogens to satisfy the valency of carbon (4 bonds per carbon).

Step 3: Create branched isomers by shortening the main chain and adding methyl (CH₃) or ethyl (C₂H₅) groups as substituents. For example, draw a six-carbon chain (hexane) and add a methyl group at different positions to create isomers like 2-methylhexane and 3-methylhexane.

Step 4: Continue branching further. For example, create a five-carbon chain (pentane) and add two methyl groups at different positions to form isomers like 2,2-dimethylpentane and 2,3-dimethylpentane. Ensure that each structure is unique and does not repeat connectivity.

Step 5: Verify that you have drawn all nine isomers by systematically checking each possible branching pattern and ensuring no duplicates. Confirm that each structure adheres to the molecular formula C₇H₁₆ and satisfies the valency rules for carbon and hydrogen.

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Key Concepts

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

Alkanes

Alkanes are saturated hydrocarbons consisting only of carbon (C) and hydrogen (H) atoms, connected by single bonds. They follow the general formula CnH2n+2, where n is the number of carbon atoms. Alkanes are characterized by their relatively low reactivity and are commonly found in natural gas and petroleum.

Constitutional Isomers

Constitutional isomers are compounds that have the same molecular formula but differ in the connectivity of their atoms. This means that the arrangement of atoms in the molecule varies, leading to different structural forms. For C₇H₁₆, the nine constitutional isomers include straight-chain and branched forms, showcasing the diversity of structures possible with the same number of atoms.

Drawing Structural Formulas

Drawing structural formulas involves representing the arrangement of atoms in a molecule, including bonds between them. For alkanes, this means illustrating the carbon backbone and the hydrogen atoms attached to each carbon. Understanding how to depict these structures is essential for visualizing isomers and their unique properties.

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Related Practice

Textbook Question

Give the relationship between the following pairs of structures. The possible relationships are:

same compound

constitutional isomers (structural isomers)

cis-trans isomers

not isomers (different molecular formula)

(g) CH₃–CH₂–CH₂–CH₃ and CH₃–CH=CH–CH₃

(h) CH₂=CH–CH₂CH₂CH₃ and CH₃–CH=CH–CH₂CH₃

(i) CH₂=CHCH₂CH₂CH₃ and CH₃CH₂CH₂CH=CH₂

Textbook Question

Draw a complete structural formula and a condensed structural formula for

b. five compounds of formula C₃H₆O

Textbook Question

Which of the following statements can be used to prove that carbon is tetrahedral?

a. CH₃Br does not have constitutional isomers.

b. CBr₄ does not have a dipole moment.

c. CH₂Br₂ does not have constitutional isomers.

Textbook Question

There are five alkane constitutional isomers with the molecular formula C₆H₁₄. Draw them.

Textbook Question

Draw four compounds with molecular formula C₅H₁₀ that have carbon–carbon double bonds but do not have cis–trans isomers.

Textbook Question

Draw and label the E and Z isomers for each of the following:

Textbook Question

What type of isomerism is indicated by each of the following pairs of molecules? Be as specific as possible.

(b)

Textbook Question

Show all possible constitutional isomers of C₅H₁₂O. Label them as functional, positional, or chain isomers.

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There are nine alkane constitutional isomers with the molecular formula C7H16. Draw them.

Key Concepts

Alkanes

Constitutional Isomers

Drawing Structural Formulas

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There are nine alkane constitutional isomers with the molecular formula C₇H₁₆. Draw them.