Draw the structure of the starting material needed to make 2-methylhept-3-yne using sodium amide in liquid ammonia, followed by 1-bromopropane. The starting hydrocarbon must have no more than five carbons 1) NaNH2, NH3() NaBr + 2) CHзCH2CH2Br In each reaction box, place the best reagent and conditions from the list below 1) 2) н Н—С—с-Н 3) 4) CH3CI H2, Lindlar catalyst H20, H2SO4, HgSO4 CH3CH2CI Br2 2-equiv. CH3CH2CH2CI ВН-/THF HBr 2-equiv. NaOH H2O2/NaOH Br2 1-equiv HBr 1-equiv. NaNH2

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter16: Aldehydes And Ketones
Section: Chapter Questions
Problem 16.55P
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Draw the structure of the starting material needed to make 2-methylhept-3-yne using sodium amide in
liquid ammonia, followed by 1-bromopropane.
The starting hydrocarbon must have
no more than five carbons
1) NaNH2, NH3()
NaBr
+
2) CHзCH2CH2Br
Transcribed Image Text:Draw the structure of the starting material needed to make 2-methylhept-3-yne using sodium amide in liquid ammonia, followed by 1-bromopropane. The starting hydrocarbon must have no more than five carbons 1) NaNH2, NH3() NaBr + 2) CHзCH2CH2Br
In each reaction box, place the best reagent and conditions from the list below
1)
2)
н
Н—С—с-Н
3)
4)
CH3CI
H2, Lindlar catalyst
H20, H2SO4, HgSO4
CH3CH2CI
Br2 2-equiv.
CH3CH2CH2CI
ВН-/THF
HBr 2-equiv.
NaOH
H2O2/NaOH
Br2 1-equiv
HBr 1-equiv.
NaNH2
Transcribed Image Text:In each reaction box, place the best reagent and conditions from the list below 1) 2) н Н—С—с-Н 3) 4) CH3CI H2, Lindlar catalyst H20, H2SO4, HgSO4 CH3CH2CI Br2 2-equiv. CH3CH2CH2CI ВН-/THF HBr 2-equiv. NaOH H2O2/NaOH Br2 1-equiv HBr 1-equiv. NaNH2
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