1) Presented below are three proposed synthetic schemes to make the target compound of 1- deutero-1-butynę. Of these three proposed schemes, only one will produce the target compound in a high yield. a) Identify the two flawed synthetic schemes. b) For each flawed synthetic scheme, Identify all of the errors. For each error, explain why this error would cause a drastic decrease in the yield of the target compound.
1) Presented below are three proposed synthetic schemes to make the target compound of 1- deutero-1-butynę. Of these three proposed schemes, only one will produce the target compound in a high yield. a) Identify the two flawed synthetic schemes. b) For each flawed synthetic scheme, Identify all of the errors. For each error, explain why this error would cause a drastic decrease in the yield of the target compound.
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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![1) Presented below are three proposed synthetic schemes to make the target compound of 1-
deutero-1-butyne. Of these three proposed schemes, only one will produce the target
compound in a high yield.
a) Identify the two flawed synthetic schemes.
b) For each flawed synthetic scheme,
Identify all of the errors.
For each error, explain why this error would cause a drastic decrease in the yield of
the target compound.
1) NaH/CH3OH.
2) CH3CH2B
D NaH /CH3OH, CHe CH2C=CD
2) D20
HCECH
CH3CH2C =CH
) NaH / Ether
2) CH3CH2 Br
1) NaH/Ether
2) D20
HC=CH
CH3CH2C=CH
→ CH3 CH2C=CD
HC=CHDNAH/Ether
2) DzO
DNAH/ Ether, CHSCH_C=CD
2) CH3CH2B
→ HC=CD](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F7c91f30a-e1bf-4b5f-a6eb-9576186b40d6%2F88b5e957-a11c-4907-9c33-4e62e6f8e673%2Fvyo86r3n_processed.png&w=3840&q=75)
Transcribed Image Text:1) Presented below are three proposed synthetic schemes to make the target compound of 1-
deutero-1-butyne. Of these three proposed schemes, only one will produce the target
compound in a high yield.
a) Identify the two flawed synthetic schemes.
b) For each flawed synthetic scheme,
Identify all of the errors.
For each error, explain why this error would cause a drastic decrease in the yield of
the target compound.
1) NaH/CH3OH.
2) CH3CH2B
D NaH /CH3OH, CHe CH2C=CD
2) D20
HCECH
CH3CH2C =CH
) NaH / Ether
2) CH3CH2 Br
1) NaH/Ether
2) D20
HC=CH
CH3CH2C=CH
→ CH3 CH2C=CD
HC=CHDNAH/Ether
2) DzO
DNAH/ Ether, CHSCH_C=CD
2) CH3CH2B
→ HC=CD
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