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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5:43 minutes

Problem 59a,b

Textbook Question

Give the relationships between the following pairs of structures. The possible relationships are as follows: same compound, cis-trans isomers, constitutional (structural) isomers, and not isomers (different molecular formula).
(a) CH₃CH₂CH₂CH₃ and (CH₃)₃CH
(b) CH₂=CH–CH₂Cl and CHCl=CH–CH₃

Verified step by step guidance

Step 1: Analyze the molecular formula of each compound in pair (a). CH3CH2CH2CH3 is a straight-chain alkane with the molecular formula C4H10, while (CH3)3CH is a branched alkane with the same molecular formula C4H10.

Step 2: Determine the relationship between the compounds in pair (a). Since both compounds have the same molecular formula but differ in connectivity (straight-chain vs branched), they are constitutional (structural) isomers.

Step 3: Analyze the molecular formula of each compound in pair (b). CH2=CHCH2Cl has the molecular formula C3H5Cl, while CHCl=CHCH3 has the molecular formula C3H5Cl as well.

Step 4: Examine the connectivity and arrangement of atoms in pair (b). CH2=CHCH2Cl has a chlorine atom attached to the terminal carbon of the propene chain, while CHCl=CHCH3 has the chlorine atom attached to the middle carbon of the propene chain. This difference in connectivity indicates that they are constitutional (structural) isomers.

Step 5: Summarize the relationships: Pair (a) consists of constitutional isomers due to different connectivity of atoms in the same molecular formula. Pair (b) also consists of constitutional isomers due to different connectivity of atoms in the same molecular formula.

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Key Concepts

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

Isomerism

Isomerism refers to the phenomenon where two or more compounds have the same molecular formula but different structural arrangements or spatial orientations. This can lead to different physical and chemical properties. The main types of isomers include structural isomers, which differ in the connectivity of atoms, and stereoisomers, which have the same connectivity but differ in the spatial arrangement of atoms.

Cis-Trans Isomerism

Cis-trans isomerism is a type of stereoisomerism that occurs in compounds with restricted rotation around a double bond or a ring structure. In cis isomers, substituents are on the same side of the double bond or ring, while in trans isomers, they are on opposite sides. This difference in arrangement can significantly affect the physical properties of the compounds, such as boiling points and solubility.

Constitutional Isomers

Constitutional isomers, also known as structural isomers, are compounds that have the same molecular formula but differ in the connectivity of their atoms. This means that the atoms are bonded together in different ways, leading to distinct compounds with unique properties. Understanding constitutional isomers is crucial for identifying relationships between different chemical structures and predicting their reactivity.

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Related Practice

Textbook Question

For the compound 1-ethyl-3-isopropylcyclopentane

Textbook Question

For each of the following molecules, draw one 3-D representation at only the necessary atoms (that is, the ones with four different atoms/groups attached).

(a)

Textbook Question

For each of the following molecules, draw one 3-D representation at only the necessary atoms (that is, the ones with four different atoms/groups attached).

(b)

Multiple Choice

Which of the following describes stereoisomers?

Textbook Question

For each pair of structures, determine whether they represent different compounds or a single compound.

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)

(a)

(b)

(c)

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)

(j)

(k)

Textbook Question

Give the relationships between the following pairs of structures. The possible relationships are as follows: same compound, cis-trans isomers, constitutional (structural) isomers, and not isomers (different molecular formula).

(c)

(d)

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Give the relationships between the following pairs of structures. The possible relationships are as follows: same ­compound, cis-trans isomers, constitutional (structural) isomers, and not isomers (different molecular formula). (a) CH3CH2CH2CH3 and (CH3)3CH (b) CH2=CH–CH2Cl and CHCl=CH–CH3

Key Concepts

Isomerism

Cis-Trans Isomerism

Constitutional Isomers

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