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

13. Alkenes, Alkynes, and Aromatic Compounds

Hydrohalogenation Reaction

GOB Chemistry

13. Alkenes, Alkynes, and Aromatic Compounds

Hydrohalogenation Reaction

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Problem 13a

Textbook Question

In the following addition reactions, are the given alkyl halides obtained as the major products? Give a reason for your answer.
a. 3-Chloro-3-ethylpentane from addition of HCl to 3-ethyl-2-pentene

Verified step by step guidance

Step 1: Identify the type of reaction. This is an electrophilic addition reaction where HCl adds across the double bond of 3-ethyl-2-pentene.

Step 2: Determine the Markovnikov's rule. According to Markovnikov's rule, in the addition of HX (where X is a halogen) to an alkene, the hydrogen atom (H) will attach to the carbon with more hydrogen atoms already bonded, and the halogen (Cl) will attach to the carbon with fewer hydrogen atoms.

Step 3: Analyze the structure of 3-ethyl-2-pentene. The double bond is between the second and third carbon atoms. The second carbon has two hydrogens, while the third carbon has one hydrogen.

Step 4: Apply Markovnikov's rule. The hydrogen from HCl will add to the second carbon (with more hydrogens), and the chlorine will add to the third carbon (with fewer hydrogens). This results in the formation of 3-chloro-3-ethylpentane.

Step 5: Confirm the product as the major product. Since the addition follows Markovnikov's rule, 3-chloro-3-ethylpentane is indeed the major product of this reaction.

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Key Concepts

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

Markovnikov's Rule

Markovnikov's Rule states that in the addition of HX to an alkene, the hydrogen atom from HX will attach to the carbon with the greater number of hydrogen atoms already attached. This principle helps predict the major product of addition reactions, as it favors the formation of more stable carbocations.

Carbocation Stability

Carbocation stability is a key factor in determining the outcome of addition reactions. Tertiary carbocations are more stable than secondary or primary ones due to hyperconjugation and inductive effects. The stability of the carbocation intermediate influences which product is formed in the reaction.

Regioselectivity

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others. In the context of alkene addition reactions, regioselectivity is influenced by factors such as carbocation stability and sterics, leading to the formation of major and minor products based on the most favorable pathway.

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Complete the following equations (Hint: Answers may include concepts learned from previous organic chapters):

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Write a hydrohalogenation reaction with excess HCl and name the organic product formed.

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Ocimene, a compound isolated from the herb basil, has three double bonds and the IUPAC name 3,7-dimethyl-1, 3-6-octatriene.

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Draw all possible products formed when 2-methyl-2-butene undergoes addition with HCl. Label them as being either the major or the minor product.

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What alkene could you use to make the following products? Draw the structure of the alkene, and tell what other reagent is also required for the reaction to occur.

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Textbook Question

1-Pentyne reacts with HBr in a 1:1 molar ratio to yield two different addition products, both being bromopentenes and having the chemical formula C₅H₉Br. Draw the structures of two possible products.

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Textbook Question

Complete the following equations (Hint: Answers may include concepts learned from previous organic chapters):

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