Organic Chemistry
Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 12, Problem 12.63P

Devise a synthesis of each compound from acetylene and any other required reagents.

a. Chapter 12, Problem 12.63P, 12.63 Devise a synthesis of each compound from acetylene and any other required reagents.
a. 	b. , example  1 b. Chapter 12, Problem 12.63P, 12.63 Devise a synthesis of each compound from acetylene and any other required reagents.
a. 	b. , example  2 c. Chapter 12, Problem 12.63P, 12.63 Devise a synthesis of each compound from acetylene and any other required reagents.
a. 	b. , example  3 d.Chapter 12, Problem 12.63P, 12.63 Devise a synthesis of each compound from acetylene and any other required reagents.
a. 	b. , example  4

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation: Synthesis of the given compound from acetylene and other required reagents is to be devised.

Concept introduction: Terminal alkynes can be converted into internal alkynes by forming new CC bond. This bond is formed by treatment of alkyne by strong base and alkyl halide.

In presence of sodium metal in ammonia, the is alkyne is reduced to trans-alkene. The addition of H2 takes place in anti fashion to the triple bond. The mechanism involves the addition of electron followed by protonation.

Answer to Problem 12.63P

Synthesis of the given compound from acetylene and other required reagents is shown in Figure 1.

Explanation of Solution

Synthesis of the given compound is shown below.

Organic Chemistry, Chapter 12, Problem 12.63P , additional homework tip  1

Figure 1

In the first step acetylene is converted to but-2-yne by forming two new CC bonds. These bonds are formed by treatment of acetylene by strong base NaNH2 and methyl bromide.

In the final step, but-2-yne is treated with Na,NH3. The addition of H2 takes place in anti fashion to the triple bond. Hence, the final product is trans-but-2-ene.

Conclusion

Synthesis of the given compound from acetylene and other required reagents is shown in Figure 1.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: Synthesis of the given compound from acetylene and other required reagents is to be devised.

Concept introduction: Terminal alkynes can be converted into internal alkynes by forming new CC bond. This bond is formed by treatment of alkyne by strong base and alkyl halide.

The addition of H2 in presence of catalyst is known as catalytic hydrogenation reaction. This is a syn addition. Alkyne is reduced to alkane. In this reaction two weak pi bond of alkene and sigma bond between H2 is broken and four CH bonds are formed.

Answer to Problem 12.63P

Synthesis of the given compound from acetylene and other required reagents is shown in Figure 2.

Explanation of Solution

Synthesis of the given compound is shown below.

Organic Chemistry, Chapter 12, Problem 12.63P , additional homework tip  2

Figure 2

In the first step acetylene is converted to 2, 7-dimethyloct-4-yne by forming two new CC bonds. These bonds are formed by treatment of acetylene by strong base NaNH2 and 2-methylbromide.

In the final step, 2, 7-dimethyloct-4-yne is treated with H2 in presence of Pd catalyst. Alkyne is reduced to alkane. Hence, the final product is 2, 7-dimethyloctane.

Conclusion

Synthesis of the given compound from acetylene and other required reagents is shown in Figure 2.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: Synthesis of the given compound from acetylene and other required reagents is to be devised.

Concept introduction: Terminal alkynes can be converted into internal alkynes by forming new CC bond. This bond is formed by treatment of alkyne by strong base and alkyl halide.

The addition of H2 in presence of catalyst is known as catalytic hydrogenation reaction. Lindlar catalyst consists of palladium deposited on calcium carbonate which is poisoned or deactivated by lead or sulfur. In presence of Lindlar catalyst, alkyne is reduced to cis-alkene.

In presence of peroxide alkene is oxidized to epoxide this is known as epoxidation. The weak pi bond of alkene and weak OO bond of peroxide are broken and two new CO bonds are formed. Breaking of bonds and formation of bonds takes place in single step. mCPBA is meta-chloroperoxybenzoicacid.

Answer to Problem 12.63P

Synthesis of the given compound from acetylene and other required reagents is shown in Figure 3.

Explanation of Solution

Synthesis of the given compound is shown below.

Organic Chemistry, Chapter 12, Problem 12.63P , additional homework tip  3

Figure 3

In the first step, acetylene is converted to but-2-yne by forming two new CC bonds. These bonds are formed by treatment of acetylene by strong base NaNH2 and methyl bromide. Then but-2-yne is treated with with H2 and Lindlar catalyst. The addition of H2 takes place in syn fashion to the triple bond. The product formed is (Z)-but-2-ene. In the final step, (Z)-but-2-ene is treated with mCPBA (meta-chloroperoxybenzoicacid), alkene is oxidized to epoxide. Hence, the final product is (2R,3S)-2, 3-dimethyloxirane.

Conclusion

Synthesis of the given compound from acetylene and other required reagents is shown in Figure 3.

Expert Solution
Check Mark
Interpretation Introduction

(d)

Interpretation: Synthesis of the given compound from acetylene and other required reagents is to be devised.

Concept introduction: Terminal alkynes can be converted into internal alkynes by forming new CC bond. This bond is formed by treatment of alkyne by strong base and alkyl halide.

The addition of H2 in presence of catalyst is known as catalytic hydrogenation reaction. Lindlar catalyst consists of palladium deposited on calcium carbonate which is poisoned or deactivated by lead or sulfur. In presence of Lindlar catalyst, alkyne is reduced to cis-alkene.

In presence of peroxide alkene is oxidized to epoxide this is known as epoxidation. The weak pi bond of alkene and weak OO bond of peroxide are broken and two new CO bonds are formed. Breaking of bonds and formation of bonds takes place in single step. mCPBA is meta-chloroperoxybenzoicacid.

Answer to Problem 12.63P

Synthesis of the given compound from acetylene and other required reagents is shown in Figure 4.

Explanation of Solution

Synthesis of the given compound is shown below.

Organic Chemistry, Chapter 12, Problem 12.63P , additional homework tip  4

Figure 4

In the first step acetylene is converted to but-2-yne by forming two new CC bonds. These bonds are formed by treatment of acetylene by strong base NaNH2 and methyl bromide. Then but-2-yne is treated with with H2 and Lindlar catalyst. The addition of H2 takes place in syn fashion to the triple bond. The product formed is (Z)-but-2-ene. In the final step, (Z)-but-2-ene is treated with mCPBA (meta-chloroperoxybenzoicacid), alkene is oxidized to epoxide. Epoxidation is followed by ring opening with H3O+. Hence, the final product is (2R,3R)-butane-2, 3-diol.

Conclusion

Synthesis of the given compound from acetylene and other required reagents is shown in Figure 4.

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Chapter 12 Solutions

Organic Chemistry

Ch. 12 - Problem 12.11 (a) Draw the structure of a compound...Ch. 12 - Prob. 12.12PCh. 12 - Prob. 12.13PCh. 12 - Problem 12.14 Draw the products of each...Ch. 12 - Prob. 12.15PCh. 12 - Problem 12.16 Draw all stereoisomers formed when...Ch. 12 - Prob. 12.17PCh. 12 - Problem 12.18 Draw the products formed when both...Ch. 12 - Problem 12.19 Draw the products formed when each...Ch. 12 - Prob. 12.20PCh. 12 - Prob. 12.21PCh. 12 - Problem 12.22 Draw the products formed when each...Ch. 12 - Prob. 12.23PCh. 12 - Problem 12.24 Draw the organic products in each of...Ch. 12 - Prob. 12.25PCh. 12 - Prob. 12.26PCh. 12 - Problem 12.27 Draw the products of each Sharpless...Ch. 12 - Prob. 12.28PCh. 12 - 12.29 Draw the products formed when A is treated...Ch. 12 - Prob. 12.30PCh. 12 - 12.31 Devise a synthesis of the following compound...Ch. 12 - Prob. 12.32PCh. 12 - Prob. 12.33PCh. 12 - Prob. 12.34PCh. 12 - Prob. 12.35PCh. 12 - Prob. 12.36PCh. 12 - 12.37 Stearidonic acid (C18H28O2) is an...Ch. 12 - Draw the organic products formed when cyclopentene...Ch. 12 - Draw the organic products formed when allylic...Ch. 12 - Draw the organic products formed in each reaction....Ch. 12 - Prob. 12.41PCh. 12 - Prob. 12.42PCh. 12 - Prob. 12.43PCh. 12 - What alkene is needed to synthesize each 1,2-diol...Ch. 12 - Prob. 12.45PCh. 12 - 12.46 (a)What product is formed in Step [1] of the...Ch. 12 - Draw the products formed after Steps 1 and 2 in...Ch. 12 - 12.48 Draw the products formed in each oxidative...Ch. 12 - What alkene or alkyne yields each set of products...Ch. 12 - Prob. 12.50PCh. 12 - Prob. 12.51PCh. 12 - Prob. 12.52PCh. 12 - Prob. 12.53PCh. 12 - 12.54 An unknown compound A of molecular formula ...Ch. 12 - 12.55 DHA is a fatty acid derived from fish oil...Ch. 12 - Prob. 12.56PCh. 12 - 12.57 Draw the product of each asymmetric...Ch. 12 - 12.58 Epoxidation of the following allylic alcohol...Ch. 12 - Prob. 12.59PCh. 12 - 12.60 Identify A in the following reaction...Ch. 12 - Prob. 12.61PCh. 12 - 12.62 It is sometimes necessary to isomerize a cis...Ch. 12 - 12.63 Devise a synthesis of each compound from...Ch. 12 - Prob. 12.64PCh. 12 - Prob. 12.65PCh. 12 - 12.66 Devise a synthesis of each compound from the...Ch. 12 - Prob. 12.67PCh. 12 - Prob. 12.68PCh. 12 - 12.69 Devise a synthesis of each compound from as...Ch. 12 - Prob. 12.70PCh. 12 - Prob. 12.71PCh. 12 - 12.72 Draw a stepwise mechanism for the following...Ch. 12 - Prob. 12.73PCh. 12 - Prob. 12.74PCh. 12 - 12.75 Sharpless epoxidation of allylic alcohol X...
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