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

8. Elimination Reactions

SN1 SN2 E1 E2 Chart (Big Daddy Flowchart)

Organic Chemistry

8. Elimination Reactions

SN1 SN2 E1 E2 Chart (Big Daddy Flowchart)

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3:16 minutes

Problem 51d

Textbook Question

Predict the product of the following reactions.
(d)

Verified step by step guidance

Step 1: Analyze the structure of the reactant. The molecule contains an iodine atom attached to a secondary carbon, which makes it a good leaving group. The presence of a bulky base, NaO-tBu (sodium tert-butoxide), suggests that the reaction will likely proceed via an E2 elimination mechanism.

Step 2: Consider the stereochemistry of the molecule. In an E2 elimination, the hydrogen to be removed must be anti-periplanar to the leaving group (iodine). Identify the β-hydrogens on the adjacent carbons and determine which hydrogen is anti-periplanar to the iodine.

Step 3: Predict the major product based on Zaitsev's rule. Zaitsev's rule states that the most substituted alkene will be the major product in an elimination reaction. However, due to the bulky base (NaO-tBu), the reaction may favor the formation of the less substituted alkene (Hofmann product). Consider steric hindrance in the elimination process.

Step 4: Draw the possible alkenes formed from the elimination reaction. Remove the iodine and the anti-periplanar β-hydrogen, forming a double bond between the α-carbon (where iodine was attached) and the β-carbon.

Step 5: Determine the major product based on the steric effects of the bulky base. The bulky base will favor the formation of the less substituted alkene, which is the Hofmann product. Ensure the stereochemistry of the product aligns with the anti-periplanar requirement of the E2 mechanism.

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Key Concepts

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

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions involve the replacement of a leaving group (like iodine) by a nucleophile. In this case, sodium tert-butoxide (NaO-t-Bu) acts as a strong nucleophile, attacking the carbon atom bonded to the iodine. Understanding the mechanism, whether it follows an SN1 or SN2 pathway, is crucial for predicting the product.

Elimination Reactions

Elimination reactions involve the removal of a small molecule (like H-I) from a larger molecule, resulting in the formation of a double bond. In the presence of a strong base like NaO-t-Bu, the reaction can lead to the formation of alkenes through either E1 or E2 mechanisms. Recognizing the conditions that favor elimination over substitution is essential for predicting the outcome.

Regioselectivity and Stereochemistry

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others. In this reaction, the formation of the double bond can lead to different alkene products depending on the site of elimination. Additionally, stereochemistry plays a role in determining the configuration of the double bond, which can affect the stability and reactivity of the product.

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