Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter14: Alcohols, Ethers, And Thiols
Section: Chapter Questions
Problem 14.48P: 14-48 Explain why methanethiol, CH3SH, has a lower boiling point (6°C) than methanol, CH3OH (65°C),...
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Question
If the Product of this Suzuki reaction is 4-(4-methylphenyl)benzaldehyde, what are the two starting reagents?
![4(4'-methylphenyl)-benzaldehyde
107 °C10
H](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F33367630-baef-4794-a3c7-3f7d1dfa9a18%2F6c2b9edd-ef50-4133-b8f4-0811db259d3e%2F36h9a9n_processed.png&w=3840&q=75)
Transcribed Image Text:4(4'-methylphenyl)-benzaldehyde
107 °C10
H
![Suzuki Cross Coupling Reaction
Synthesis of an Unsymmetrical Biaryl via a Suzuki Cross Coupling Reaction'
Experimental Goals:
Perform the cross coupling reaction from two unknown coupling partners and isolate the product.
Determine the structure of the product from its IR and NMR spectra and melting point, and in tum
determine the starting materials.
B(OH)2
Pd(OAc)2, PPH3
аq NazCOs
Br
R'
n-PrOH
R = H, CH3
R' = H, CH3, OCH3
R"
Name
Structure
mp
1-biphenyl-4-yl-ethanone
120-121°C*
CHS
1-biphenyl-4-yl-ethanol
96-98 °C
CH3
biphenyl-4-carbaldehyde
60-63 "C
OH
4-phenyl-benzyl alcohol
104-105 °C"
H.
1-(4"-methyl-biphenyl-4-yl) ethanone
119-120 °C
CH3
OH
1-(4'methyl-biphenyl-4-yl)-ethanol
95-96 "C"
CH3
4(4'-methylphenyl)-benzaldehyde
107 °C"
он
4'-methyl-(biphenyl-4-yl)-methanol
100-101 "C
H.
1-(4"-methoxy-biphenyl-4-yl)-ethanone
Meo
153-154 "C2
CH3
OH
1-(4'-methoxy-biphenyl-4-yl)-ethanol
Meo
120-122 °C
CH3
4'-methoxy-biphenyl-4-carbaldehyde
Meo
105-106 "C4
H.
OH
4'-methoxy-biphenyl-4-yl-methanol
162-163 "C
Meo](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F33367630-baef-4794-a3c7-3f7d1dfa9a18%2F6c2b9edd-ef50-4133-b8f4-0811db259d3e%2Fs0lm1c_processed.png&w=3840&q=75)
Transcribed Image Text:Suzuki Cross Coupling Reaction
Synthesis of an Unsymmetrical Biaryl via a Suzuki Cross Coupling Reaction'
Experimental Goals:
Perform the cross coupling reaction from two unknown coupling partners and isolate the product.
Determine the structure of the product from its IR and NMR spectra and melting point, and in tum
determine the starting materials.
B(OH)2
Pd(OAc)2, PPH3
аq NazCOs
Br
R'
n-PrOH
R = H, CH3
R' = H, CH3, OCH3
R"
Name
Structure
mp
1-biphenyl-4-yl-ethanone
120-121°C*
CHS
1-biphenyl-4-yl-ethanol
96-98 °C
CH3
biphenyl-4-carbaldehyde
60-63 "C
OH
4-phenyl-benzyl alcohol
104-105 °C"
H.
1-(4"-methyl-biphenyl-4-yl) ethanone
119-120 °C
CH3
OH
1-(4'methyl-biphenyl-4-yl)-ethanol
95-96 "C"
CH3
4(4'-methylphenyl)-benzaldehyde
107 °C"
он
4'-methyl-(biphenyl-4-yl)-methanol
100-101 "C
H.
1-(4"-methoxy-biphenyl-4-yl)-ethanone
Meo
153-154 "C2
CH3
OH
1-(4'-methoxy-biphenyl-4-yl)-ethanol
Meo
120-122 °C
CH3
4'-methoxy-biphenyl-4-carbaldehyde
Meo
105-106 "C4
H.
OH
4'-methoxy-biphenyl-4-yl-methanol
162-163 "C
Meo
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