(a) Interpretation: The missing reactant that is necessary to carry out the given transformation is to be drawn. Concept introduction: The palladium catalysed reactions are namely Suzuki coupling and Heck coupling which form a 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 conditions. 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.

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Answer 1

Question

Chapter 19, Problem 19.60P

Interpretation Introduction

(a)

Interpretation:

The missing reactant that is necessary to carry out the given transformation is to be drawn.

Concept introduction:

The palladium catalysed reactions are namely Suzuki coupling and Heck coupling which form a 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 conditions. 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.

Interpretation Introduction

(b)

Interpretation:

Concept introduction:

The palladium catalysed reactions are namely Suzuki coupling and Heck coupling which form a 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 conditions. 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.

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1) a) Give the dominant Intermolecular Force (IMF) in a sample of each of the following compounds. Please show your work. (8) SF2, CH,OH, C₂H₂ b) Based on your answers given above, list the compounds in order of their Boiling Point from low to high. (8)

19.78 Write the products of the following sequences of reactions. Refer to your reaction road- maps to see how the combined reactions allow you to "navigate" between the different functional groups. Note that you will need your old Chapters 6-11 and Chapters 15-18 roadmaps along with your new Chapter 19 roadmap for these. (a) 1. BHS 2. H₂O₂ 3. H₂CrO4 4. SOCI₂ (b) 1. Cl₂/hv 2. KOLBU 3. H₂O, catalytic H₂SO4 4. H₂CrO4 Reaction Roadmap An alkene 5. EtOH 6.0.5 Equiv. NaOEt/EtOH 7. Mild H₂O An alkane 1.0 2. (CH3)₂S 3. H₂CrO (d) (c) 4. Excess EtOH, catalytic H₂SO OH 4. Mild H₂O* 5.0.5 Equiv. NaOEt/EtOH An alkene 6. Mild H₂O* A carboxylic acid 7. Mild H₂O* 1. SOC₁₂ 2. EtOH 3.0.5 Equiv. NaOEt/E:OH 5.1.0 Equiv. NaOEt 6. NH₂ (e) 1. 0.5 Equiv. NaOEt/EtOH 2. Mild H₂O* Br (f) i H An aldehyde 1. Catalytic NaOE/EtOH 2. H₂O*, heat 3. (CH,CH₂)₂Culi 4. Mild H₂O* 5.1.0 Equiv. LDA Br An ester 4. NaOH, H₂O 5. Mild H₂O* 6. Heat 7. MgBr 8. Mild H₂O* 7. Mild H₂O+

Answer 2

Question

Chapter 19, Problem 19.60P

Interpretation Introduction

(a)

Interpretation:

The missing reactant that is necessary to carry out the given transformation is to be drawn.

Concept introduction:

The palladium catalysed reactions are namely Suzuki coupling and Heck coupling which form a 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 conditions. 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.

Interpretation Introduction

(b)

Interpretation:

Concept introduction:

The palladium catalysed reactions are namely Suzuki coupling and Heck coupling which form a 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 conditions. 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.

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Answer 3

Question

Chapter 19, Problem 19.60P

Interpretation Introduction

(a)

Interpretation:

The missing reactant that is necessary to carry out the given transformation is to be drawn.

Concept introduction:

The palladium catalysed reactions are namely Suzuki coupling and Heck coupling which form a 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 conditions. 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.

Interpretation Introduction

(b)

Interpretation:

Concept introduction:

The palladium catalysed reactions are namely Suzuki coupling and Heck coupling which form a 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 conditions. 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.

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Answer 4

Question

Chapter 19, Problem 19.60P

Interpretation Introduction

(a)

Interpretation:

The missing reactant that is necessary to carry out the given transformation is to be drawn.

Concept introduction:

The palladium catalysed reactions are namely Suzuki coupling and Heck coupling which form a 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 conditions. 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.

Interpretation Introduction

(b)

Interpretation:

Concept introduction:

The palladium catalysed reactions are namely Suzuki coupling and Heck coupling which form a 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 conditions. 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.

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Answer 5

Chapter 19, Problem 19.60P

Interpretation Introduction

(a)

Interpretation:

The missing reactant that is necessary to carry out the given transformation is to be drawn.

Concept introduction:

The palladium catalysed reactions are namely Suzuki coupling and Heck coupling which form a 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 conditions. 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.

Interpretation Introduction

(b)

Interpretation:

Concept introduction:

The palladium catalysed reactions are namely Suzuki coupling and Heck coupling which form a 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 conditions. 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.

Answer 6

Chapter 19, Problem 19.60P

Interpretation Introduction

(a)

Interpretation:

The missing reactant that is necessary to carry out the given transformation is to be drawn.

Concept introduction:

The palladium catalysed reactions are namely Suzuki coupling and Heck coupling which form a 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 conditions. 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.

Answer 7

Chapter 19, Problem 19.60P

Interpretation Introduction

(a)

Interpretation:

The missing reactant that is necessary to carry out the given transformation is to be drawn.

Concept introduction:

The palladium catalysed reactions are namely Suzuki coupling and Heck coupling which form a 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 conditions. 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.

Answer 8

Interpretation Introduction

(b)

Interpretation:

Concept introduction:

The palladium catalysed reactions are namely Suzuki coupling and Heck coupling which form a 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 conditions. 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.

Answer 9

Interpretation Introduction

(b)

Interpretation:

Concept introduction:

The palladium catalysed reactions are namely Suzuki coupling and Heck coupling which form a 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 conditions. 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.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 19 - Prob. 19.1P Ch. 19 - Prob. 19.2P Ch. 19 - Prob. 19.3P Ch. 19 - Prob. 19.4P Ch. 19 - Prob. 19.5P Ch. 19 - Prob. 19.6P Ch. 19 - Prob. 19.7P Ch. 19 - Prob. 19.8P Ch. 19 - Prob. 19.9P Ch. 19 - Prob. 19.10P

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