Organic Chemistry: Principles and Mechanisms (Second Edition)
Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
Question
Book Icon
Chapter 19, Problem 19.61P
Interpretation Introduction

(a)

Interpretation:

The Major organic product of the given reaction is to be determined.

Concept introduction:

The palladium catalyzed reactions are namely Suzuki coupling and Heck coupling which formed new C-C bond. In Suzuki coupling reaction, a vinylic or aryl halide R-X is treated with an organometallic compound R’-B(OR”)2 and a palladium catalyst (PdLn) under basic condition. Suzuki reaction is stereospecific involving possible E/Z isomerism usually with retention of configuration. Similar to the Suzuki reaction, the Heck reaction can couple one vinylic or aryl group to another. If R-X halide in a Heck reaction is vinylic, the configuration about the double bond is retained. If H-R’ is vinylic and has an attached substituent at the opposite end of the C=C, then R and the substituent will be trans to each other in the product.

Expert Solution
Check Mark

Answer to Problem 19.61P

The major product of given Suzuki reaction of R-X and R’-B(OR”)2 is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 19, Problem 19.61P , additional homework tip  1

Explanation of Solution

The Suzuki coupling reaction forms a new C-C bond between R-X and R’-B(OR”)2 in presence of palladium catalyst. The new C-C bond is formed between R group of aryl halide and R’ group of boron containing compound. The reaction proceeds with retention of configuration.

Therefore, the overall Suzuki reaction is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 19, Problem 19.61P , additional homework tip  2

Conclusion

Suzuki reaction, involving possible E/Z isomerism, usually proceeds with retention of configuration C=C double bond.

Interpretation Introduction

(b)

Interpretation:

The Major organic product of the given reaction is to be determined.

Concept introduction:

The palladium catalyzed reactions are namely Suzuki coupling and Heck coupling which formed new C-C bond. In Suzuki coupling reaction, a vinylic or aryl halide R-X is treated with an organometallic compound R’-B(OR”)2 and a palladium catalyst (PdLn) under basic condition. Suzuki reaction is stereospecific involving possible E/Z isomerism usually with retention of configuration. Similar to the Suzuki reaction, the Heck reaction can couple one vinylic or aryl group to another. If R-X halide in a Heck reaction is vinylic, the configuration about the double bond is retained. If H-R’ is vinylic and has an attached substituent at the opposite end of the C=C, then R and the substituent will be trans to each other in the product.

Expert Solution
Check Mark

Answer to Problem 19.61P

The major product of the given Suzuki reaction of R-X and R’-B(OR”)2 is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 19, Problem 19.61P , additional homework tip  3

Explanation of Solution

The Suzuki coupling reaction forms a new C-C bond between R-X and R’-B(OR”)2 in presence of palladium catalyst. The new C-C bond is formed between R group of aryl halide and R’ group of boron containing compound. The reaction proceeds with retention of configuration.

Therefore, the overall Suzuki reaction is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 19, Problem 19.61P , additional homework tip  4

Conclusion

Suzuki reaction involving possible E/Z isomerism usually proceeds with retention of configuration of C=C double bond.

Interpretation Introduction

(c)

Interpretation:

The Major organic product of the given reaction is to be determined.

Concept introduction:

The palladium catalyzed reactions are namely Suzuki coupling and Heck coupling which formed new C-C bond. In Suzuki coupling reaction, a vinylic or aryl halide R-X is treated with an organometallic compound R’-B(OR”)2 and a palladium catalyst (PdLn) under basic condition. Suzuki reaction is stereospecific involving possible E/Z isomerism usually with retention of configuration. Similar to the Suzuki reaction, the Heck reaction can couple one vinylic or aryl group to another. If R-X halide in a Heck reaction is vinylic, the configuration about the double bond is retained. If H-R’ is vinylic and has an attached substituent at the opposite end of the C=C, then R and the substituent will be trans to each other in the product.

Expert Solution
Check Mark

Answer to Problem 19.61P

The major product of given Heck reaction of R-X and R’-H is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 19, Problem 19.61P , additional homework tip  5

Explanation of Solution

In the given Heck reaction, a new C-C bond is formed between R from R-X and R’ from H-R’. If H-R’ is vinylic and has an attached substituent that is Ph at the opposite end of the C=C, then R and the substituent attached are trans to each other.

Therefore, the overall Heck reaction is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 19, Problem 19.61P , additional homework tip  6

Conclusion

If the R-X halide in Heck reaction is vinylic, the configuration about the double bond is retained. If H-R’ is vinylic and has an attached substituent at the opposite end of C=C, then R and the substituent will be trans to each other in the product.

Interpretation Introduction

(d)

Interpretation:

The Major organic product of the given reaction is to be determined.

Concept introduction:

The palladium catalyzed reactions are namely Suzuki coupling and Heck coupling which formed new C-C bond. In Suzuki coupling reaction, a vinylic or aryl halide R-X is treated with an organometallic compound R’-B(OR”)2 and a palladium catalyst (PdLn) under basic condition. Suzuki reaction is stereospecific involving possible E/Z isomerism usually with retention of configuration. Similar to the Suzuki reaction, the Heck reaction can couple one vinylic or aryl group to another. If R-X halide in a Heck reaction is vinylic, the configuration about the double bond is retained. If H-R’ is vinylic and has an attached substituent at the opposite end of the C=C, then R and the substituent will be trans to each other in the product.

Expert Solution
Check Mark

Answer to Problem 19.61P

The major product of given Heck reaction of R-X and R’-H is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 19, Problem 19.61P , additional homework tip  7

Explanation of Solution

The CH3CH2CH=CH substituent on R’-H becomes trans to the R substituent from R-X. In this reaction, the Cis configuration about the C=C in the R-Br reactant is retained.

Therefore, the overall Heck reaction is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 19, Problem 19.61P , additional homework tip  8

Conclusion

If the R-X halide in Heck reaction is vinylic, the configuration about the double bond is retained. If R’-H is vinylic and has an attached substituent at the opposite end of C=C, then R and the substituent will be trans to each other in the product.

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Chapter 19 Solutions

Organic Chemistry: Principles and Mechanisms (Second Edition)

Ch. 19 - Prob. 19.11PCh. 19 - Prob. 19.12PCh. 19 - Prob. 19.13PCh. 19 - Prob. 19.14PCh. 19 - Prob. 19.15PCh. 19 - Prob. 19.16PCh. 19 - Prob. 19.17PCh. 19 - Prob. 19.18PCh. 19 - Prob. 19.19PCh. 19 - Prob. 19.20PCh. 19 - Prob. 19.21PCh. 19 - Prob. 19.22PCh. 19 - Prob. 19.23PCh. 19 - Prob. 19.24PCh. 19 - Prob. 19.25PCh. 19 - Prob. 19.26PCh. 19 - Prob. 19.27PCh. 19 - Prob. 19.28PCh. 19 - Prob. 19.29PCh. 19 - Prob. 19.30PCh. 19 - Prob. 19.31PCh. 19 - Prob. 19.32PCh. 19 - Prob. 19.33PCh. 19 - Prob. 19.34PCh. 19 - Prob. 19.35PCh. 19 - Prob. 19.36PCh. 19 - Prob. 19.37PCh. 19 - Prob. 19.38PCh. 19 - Prob. 19.39PCh. 19 - Prob. 19.40PCh. 19 - Prob. 19.41PCh. 19 - Prob. 19.42PCh. 19 - Prob. 19.43PCh. 19 - Prob. 19.44PCh. 19 - Prob. 19.45PCh. 19 - Prob. 19.46PCh. 19 - Prob. 19.47PCh. 19 - Prob. 19.48PCh. 19 - Prob. 19.49PCh. 19 - Prob. 19.50PCh. 19 - Prob. 19.51PCh. 19 - Prob. 19.52PCh. 19 - Prob. 19.53PCh. 19 - Prob. 19.54PCh. 19 - Prob. 19.55PCh. 19 - Prob. 19.56PCh. 19 - Prob. 19.57PCh. 19 - Prob. 19.58PCh. 19 - Prob. 19.59PCh. 19 - Prob. 19.60PCh. 19 - Prob. 19.61PCh. 19 - Prob. 19.62PCh. 19 - Prob. 19.63PCh. 19 - Prob. 19.64PCh. 19 - Prob. 19.65PCh. 19 - Prob. 19.66PCh. 19 - Prob. 19.67PCh. 19 - Prob. 19.68PCh. 19 - Prob. 19.69PCh. 19 - Prob. 19.70PCh. 19 - Prob. 19.71PCh. 19 - Prob. 19.72PCh. 19 - Prob. 19.73PCh. 19 - Prob. 19.74PCh. 19 - Prob. 19.75PCh. 19 - Prob. 19.76PCh. 19 - Prob. 19.77PCh. 19 - Prob. 19.78PCh. 19 - Prob. 19.79PCh. 19 - Prob. 19.1YTCh. 19 - Prob. 19.2YTCh. 19 - Prob. 19.3YTCh. 19 - Prob. 19.4YTCh. 19 - Prob. 19.5YTCh. 19 - Prob. 19.6YTCh. 19 - Prob. 19.7YTCh. 19 - Prob. 19.8YTCh. 19 - Prob. 19.9YTCh. 19 - Prob. 19.10YT
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