OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
8th Edition
ISBN: 9781305582439
Author: Brown, William H.; Iverson, Brent L.; Anslyn, Eric; Foote, Christopher S.
Publisher: Cengage Learning
Question
Book Icon
Chapter 24, Problem 24.28P
Interpretation Introduction

Interpretation:

The proper reactant and the proper coupling reaction pathway have to be suggested for the given polymers in the question.

Concept Introduction:

Cross coupling:

A cross coupling reaction is defined as a reaction that creates a CC bond by coupling together two alkyl, aryl, alkenyl or alkynyl groups.  Cross coupling reactions involve a transmetallation step.  A transmetallation is a pairwise interchange of ligands between two different metals or metalloids.

In the case of palladium catalysed cross-coupling reactions the other metal or metalloids are commonly Zr,Sn,B,ZN,Cu,Mg which are designated as M in the following general example,

R-Pd+R'-MR'-Pd+R-M

Sonogashira coupling:

The Pd(0) catalyzed cross coupling reaction that involves transmetallation of an alkynyl Cu(I) species to Pd follow by the coupling to an aryl or vinyl iodide or triflate.  The Cu(I) alkynyl complex is created in situ by the reaction of terminal alkyne with CuI in the presence of trimethylamine.  This reaction is most commonly used to create diaryl alkynyl product.

Generalized reaction,

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 24, Problem 24.28P

Suzuki coupling:

The Suzuki coupling uses a boron compound and an alkenyl, aryl or alkyl halide or triflate as the carbon sources with a palladium salt as a catalyst.  The reaction is mainly used to form biaryls.  The mechanism of the reaction starts with an oxidative addition followed by transmetallation in which the substituent on the borane replaces the ligand on the palladium concluding with the reductive elimination of the palladium to form the new carbon-carbon bond.  The base may serve as a new labile ligand to palladium or it may activate the borane by coordination.

Generalized reaction,

RX+R'BY2basePdL4R-R'+XBY2

Oxidative addition and ligand exchange,

RXPdLnR-PdXRO-R-Pd-OR

Borane activation

BY3RO-[RO-BY3]-

Reaction,

R-Pd-OR+[R'-BY3]-R-Pd-R'R-R'+Pd(0)+[RO-BY3]-

Blurred answer
Students have asked these similar questions
LTS Solid: AT=Te-Ti Trial 1 Trial 2 Trial 3 Average ΔΗ Mass water, g 24.096 23.976 23.975 Moles of solid, mol 0.01763 001767 0101781 Temp. change, °C 2.9°C 11700 2.0°C Heat of reaction, J -292.37J -170.473 -193.26J AH, kJ/mole 16.58K 9.647 kJ 10.85 kr 16.58K59.64701 KJ mol 12.35k Minimum AS, J/mol K 41.582 mol-k Remember: q = mCsAT (m = mass of water, Cs=4.184J/g°C) & qsin =-qrxn & Show your calculations for: AH in J and then in kJ/mole for Trial 1: qa (24.0969)(4.1845/g) (-2.9°C)=-292.37J qsin = qrxn = 292.35 292.37J AH in J = 292.375 0.2923kJ 0.01763m01 =1.65×107 AH in kJ/mol = = 16.58K 0.01763mol mol qrx Minimum AS in J/mol K (Hint: use the average initial temperature of the three trials, con Kelvin.) AS=AHIT (1.65×10(9.64×103) + (1.0 Jimai
For the compound: C8H17NO2 Use the following information to come up with a plausible structure: 8 This compound has "carboxylic acid amide" and ether functional groups. The peaks at 1.2ppm are two signals that are overlapping one another. One of the two signals is a doublet that represents 6 hydrogens; the other signal is a quartet that represents 3 hydrogens.
Vnk the elements or compounds in the table below in decreasing order of their boiling points. That is, choose 1 next to the substance with the highest bolling point, choose 2 next to the substance with the next highest boiling point, and so on. substance C D chemical symbol, chemical formula or Lewis structure. CH,-N-CH, CH, H H 10: H C-C-H H H H Cale H 10: H-C-C-N-CH, Bri CH, boiling point (C) Сен (C) B (Choose
Knowledge Booster
Background pattern image
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
  • Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305580350
    Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
    Publisher:Cengage Learning
    Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305080485
    Author:John E. McMurry
    Publisher:Cengage Learning
    Text book image
    Organic Chemistry: A Guided Inquiry
    Chemistry
    ISBN:9780618974122
    Author:Andrei Straumanis
    Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305080485
Author:John E. McMurry
Publisher:Cengage Learning
Text book image
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning