Organic Chemistry
Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 8, Problem 8.1P

Label the α and β carbons in each alkyl halide. Draw all possible elimination products formed when each alkyl halide is treated with K +- O ( CH 3 ) 3 .

a.Chapter 8, Problem 8.1P, Problem 8.1 Label the  and  carbons in each alkyl halide. Draw all possible elimination products , example  1 b.Chapter 8, Problem 8.1P, Problem 8.1 Label the  and  carbons in each alkyl halide. Draw all possible elimination products , example  2 c.Chapter 8, Problem 8.1P, Problem 8.1 Label the  and  carbons in each alkyl halide. Draw all possible elimination products , example  3

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation: α and β carbons are to be labeled in the given alkyl halide and all the possible elimination products are to be drawn.

Concept introduction: Carbon atom to which the halogen atom is attached is known as α carbon atom while the carbon atom adjacent to the α carbon atom is known as β carbon atom. Alkyl halides in the presence of a base undergo dehydrohalogenation reaction.

Answer to Problem 8.1P

α and β carbons are labeled in the given alkyl halide and its elimination product is,

Organic Chemistry, Chapter 8, Problem 8.1P , additional homework tip  1

Explanation of Solution

There are different types of carbon atoms present in an alkyl halide depending on their relative position to the halogen atom. α carbon atom-directly attached to the carbon atom bearing the halogen, β carbon atom- adjacent to the α carbon atom, δ-adjacent to the β carbon atom. When an alkyl halide is treated with a base, a proton is abstracted from the β carbon atom leading to dehydrohalogenation reaction. As the given base is bulky, the least substituted alkene is the most favored product. 1-Chloropentane undergoes dehydrohalogenation in the presence of strong base K+-OC(CH3)3 to form Pent-1-ene.

Organic Chemistry, Chapter 8, Problem 8.1P , additional homework tip  2

Figure 1

Organic Chemistry, Chapter 8, Problem 8.1P , additional homework tip  3

Figure 2

Conclusion

α and β carbons are labeled in 1-Chloropentane and its elimination product is drawn.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: α and β carbons are to be labeled in the given alkyl halide and all the possible elimination products are to be drawn..

Concept introduction: Carbon atom to which the halogen atom is attached is known as α carbon atom while the carbon atom adjacent to the α carbon atom is known as β carbon atom. Alkyl halides in the presence of a base undergo dehydrohalogenation reaction.

Answer to Problem 8.1P

α and β carbons are labeled in the given alkyl halide and its elimination product is,

Organic Chemistry, Chapter 8, Problem 8.1P , additional homework tip  4

Explanation of Solution

There are different types of carbon atoms present in an alkyl halide depending on their relative position to the halogen atom. α carbon atom-directly attached to the carbon atom bearing the halogen, β carbon atom- adjacent to the α carbon atom, δ-adjacent to the β carbon atom. When an alkyl halide is treated with a base, a proton is abstracted from the β carbon atom leading to dehydrohalogenation reaction. As the given base is bulky the least substituted alkene is the most favored product, 3-Chloro-3-methylpentane undergoes dehydrohalogenation in the presence of strong base K+-OC(CH3)3 to form 3-Methylenepentane and 3-Methylpent-2-ene. The least substituted alkene is the most favored product due to the bulky base used. Therefore, 3-Methylenepentane is the major product.

Organic Chemistry, Chapter 8, Problem 8.1P , additional homework tip  5

Figure 3

Organic Chemistry, Chapter 8, Problem 8.1P , additional homework tip  6

Figure 4

Conclusion

α and β carbons are labeled in 3-Chloro-3-methylpentane and its elimination product is drawn.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: α and β carbons are to be labeled in the given alkyl halide and all the possible elimination products are to be drawn.

Concept introduction: Carbon atom to which the halogen atom is attached is known as α carbon atom while the carbon atom adjacent to the α carbon atom is known as β carbon atom. Alkyl halides in the presence of a base undergo dehydrohalogenation reaction.

Answer to Problem 8.1P

α and β carbons are labeled in the given alkyl halide and its elimination product is,

Organic Chemistry, Chapter 8, Problem 8.1P , additional homework tip  7

Explanation of Solution

There are different types of carbon atoms present in an alkyl halide depending on their relative position to the halogen atom. α carbon atom-directly attached to the carbon atom bearing the halogen, β carbon atom- adjacent to the α carbon atom, δ-adjacent to the β carbon atom. When an alkyl halide is treated with a base, a proton is abstracted from the β carbon atom leading to dehydrohalogenation reaction. As the given base is bulky the least substituted alkene is the most favored product, 1-Bromo-1-methylcyclohexane undergoes dehydrohalogenation in the presence of strong base K+-OC(CH3)3 to form Methylenecyclohexane and 1-Methylcyclohex-1-ene. Since the least substituted alkene is the most favored product due to the bulky base used, Methylenecyclohexane is the major product.

Organic Chemistry, Chapter 8, Problem 8.1P , additional homework tip  8

Figure 5

Organic Chemistry, Chapter 8, Problem 8.1P , additional homework tip  9

Figure 6

Conclusion

α and β carbons are labeled in 1-Bromo-1-methylcyclohexane and its elimination product is drawn.

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Chapter 8 Solutions

Organic Chemistry

Ch. 8 - Prob. 8.11PCh. 8 - Problem 8.12 What alkenes are formed from each...Ch. 8 - Prob. 8.13PCh. 8 - Problem 8.14 What alkenes are formed from each...Ch. 8 - Problem 8.15 How does each of the following...Ch. 8 - Problem 8.16 Draw both the SN1 and E1 products of...Ch. 8 - Prob. 8.17PCh. 8 - Prob. 8.18PCh. 8 - Problem 8.19 Explain why...Ch. 8 - Prob. 8.20PCh. 8 - Problem 8.21 Draw the alkynes formed when each...Ch. 8 - Problem 8.22 Draw the products in each...Ch. 8 - Problem 8.23 Draw a stepwise mechanism for the...Ch. 8 - 8.24 Rank the alkenes shown in the ball-and-stick...Ch. 8 - Prob. 8.25PCh. 8 - 8.26 What is the major E2 elimination product...Ch. 8 - Prob. 8.27PCh. 8 - Prob. 8.28PCh. 8 - Prob. 8.29PCh. 8 - 8.30 Label each pair of alkenes as constitutional...Ch. 8 - Prob. 8.31PCh. 8 - Prob. 8.32PCh. 8 - Prob. 8.33PCh. 8 - For each of the following alkenes, draw the...Ch. 8 - Prob. 8.35PCh. 8 - Prob. 8.36PCh. 8 - Prob. 8.37PCh. 8 - What alkene is the major product formed from each...Ch. 8 - Prob. 8.39PCh. 8 - Prob. 8.40PCh. 8 - Pick the reactant or solvent in each part that...Ch. 8 - 8.42 In the dehydrohalogenation of...Ch. 8 - Prob. 8.43PCh. 8 - Prob. 8.44PCh. 8 - Prob. 8.45PCh. 8 - Prob. 8.46PCh. 8 - Prob. 8.47PCh. 8 - Prob. 8.48PCh. 8 - What alkyl chloride affords the following alkene...Ch. 8 - Draw the products formed when each dihalide is...Ch. 8 - Draw the structure of a dihalide that could be...Ch. 8 - Under certain reaction conditions, 2,...Ch. 8 - For which reaction mechanisms, SN1, SN2, E1 or...Ch. 8 - Draw the organic products formed in each...Ch. 8 - Prob. 8.55PCh. 8 - Draw all products, including stereoisomers, in...Ch. 8 - Draw all of the substitution and elimination...Ch. 8 - Prob. 8.58PCh. 8 - 8.59 Draw a stepwise, detailed mechanism for each...Ch. 8 - Draw the major product formed when...Ch. 8 - Draw a stepwise, detailed mechanism for the...Ch. 8 - Explain why the reaction of with gives ...Ch. 8 - Draw a stepwise detailed mechanism that...Ch. 8 - Prob. 8.64PCh. 8 - 8.65 Explain the selectivity observed in the...Ch. 8 - Prob. 8.66PCh. 8 - Prob. 8.67PCh. 8 - 8.68 (a) Draw all products formed by treatment of...
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