Table of contents

1. Matter and Measurements4h 31m
2. Atoms and the Periodic Table5h 23m
3. Ionic Compounds2h 18m
4. Molecular Compounds2h 18m
5. Classification & Balancing of Chemical Reactions3h 17m
6. Chemical Reactions & Quantities2h 27m
7. Energy, Rate and Equilibrium3h 46m
8. Gases, Liquids and Solids3h 25m
9. Solutions4h 10m
10. Acids and Bases3h 29m
11. Nuclear Chemistry56m
BONUS: Lab Techniques and Procedures1h 38m
BONUS: Mathematical Operations and Functions47m
12. Introduction to Organic Chemistry1h 34m
13. Alkenes, Alkynes, and Aromatic Compounds2h 12m
14. Compounds with Oxygen or Sulfur1h 6m
15. Aldehydes and Ketones1h 1m
16. Carboxylic Acids and Their Derivatives1h 11m
17. Amines39m
18. Amino Acids and Proteins1h 51m
19. Enzymes1h 37m
20. Carbohydrates1h 41m
21. The Generation of Biochemical Energy2h 8m
22. Carbohydrate Metabolism2h 22m
23. Lipids2h 26m
24. Lipid Metabolism1h 45m
25. Protein and Amino Acid Metabolism1h 37m
26. Nucleic Acids and Protein Synthesis2h 54m

14. Compounds with Oxygen or Sulfur

Alcohol Reactions: Dehydration Reactions

GOB Chemistry

14. Compounds with Oxygen or Sulfur

Alcohol Reactions: Dehydration Reactions

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Problem 8b

Textbook Question

What alkenes might be formed by dehydration of the following alcohols? If more than one product is possible in a given case, indicate which is major.
b.

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Identify the alcohol structure in the given problem. Dehydration of alcohols involves the removal of a water molecule, which typically occurs when the alcohol is heated in the presence of an acid catalyst (e.g., H₂SO₄ or H₃PO₄).

Determine the possible β-hydrogens (hydrogens on the carbon adjacent to the carbon bearing the hydroxyl group) that can be eliminated along with the hydroxyl group (-OH). This will help identify the potential alkenes that can form.

Apply Zaitsev's rule, which states that the major product of an elimination reaction is the more substituted alkene (the one with the greater number of alkyl groups attached to the double-bonded carbons). This will help you predict the major product.

Draw the structures of all possible alkenes that can form by removing a β-hydrogen from different adjacent carbons. Ensure that you account for all possible elimination pathways.

Indicate which alkene is the major product based on Zaitsev's rule. If there are multiple products, clearly label the major and minor products.

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Key Concepts

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

Dehydration Reaction

Dehydration is a chemical reaction that involves the removal of a water molecule from a compound. In organic chemistry, this often refers to the conversion of alcohols into alkenes by eliminating a hydroxyl group and a hydrogen atom. This reaction typically requires an acid catalyst and can lead to the formation of multiple products depending on the structure of the alcohol.

Zaitsev's Rule

Zaitsev's Rule states that in elimination reactions, the more substituted alkene is usually the major product. This principle helps predict the outcome of dehydration reactions by favoring the formation of alkenes that have more alkyl groups attached to the double bond, which results in greater stability due to hyperconjugation and inductive effects.

Regioselectivity

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple products are possible. In the context of dehydration of alcohols, regioselectivity determines which alkene is formed based on the stability of the resulting double bond and the position of the substituents, influencing the major product in the reaction.

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Using the alcohol shown, draw all the possible alkenes that might be formed on its dehydration. Which do you think will be the major product(s)? Which do you think will be the minor product(s)? It is alright to have more than one major and minor product.

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Using the alcohol shown, draw all the possible alkenes that might be formed on its dehydration. Which alkenes can exist as cis–trans isomers? Draw them, in both condensed and line structure, and identify each as cis or trans. Explain your choices.

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What alcohols yield the following alkenes as the major product on dehydration?

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Predict the product of the following reaction:

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