Answer Happy

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 HCECH → CH3CH2C=CH 2) CH3CH2 Br 2) Dzo D) Nally /CH30H, CH3CH2C=CD 1) Nah / Ether HCECH → CH3CH2C=CH 1) Nah/ Ether 2) CH3 CH2 Br 2) Dzo CH3CH2C=CD o) Nahl Ether, HCECH DNahl/Ether HC=CD 2) Dzo 2) CH3 CH₂ Br CH3CH2C=CD 2) Using cyclohexene, ethyne, and bromoalkanes with three or fewer carbon atoms as the only source of carbon compounds, propose a synthesis of each target molecule. Your synthesis must show reaction conditions and solvents for each synthetic step. CHCHZ