14. Synthetic Techniques
Alkynide Alkylation
14. Synthetic Techniques
Alkynide Alkylation - Video Tutorials & Practice Problems
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Get a 10 bullets summary of the topicOrganometals aren't the only way to create new carbon-carbon bonds. It turns out we can use a sodium alkynide (nucleophile) as well to react with alkyl halides and other electrophiles to form a new C-C bond as well.
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1
concept
Sodium Alkynide Alkylation
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Video transcript
Once we create these triple bond nucleophiles and use them in our synthesis, we will will also learn how to get rid of them and transform them to double bonds (cis and trans) and single bonds.
Let's get to work. These will be multi-step transformations. Do your best to see if you can fill in the correct reagents!
2
Problem
ProblemPropose a synthesis:
A
1) H2/Lindlar's Catalyst
2) KMnO4, OH-, Δ / H+ 3) NaBH4
4) CH3MgBr
2) KMnO4, OH-, Δ / H+ 3) NaBH4
4) CH3MgBr
B
1) LiAlH
2) CH3Cl 3) H2/Pt
2) CH3Cl 3) H2/Pt
C
1) NaNH2
2) CH3Br 3) H2/Lindlar's catalyst
2) CH3Br 3) H2/Lindlar's catalyst
D
1) O3, Me2S
2) EtLi / H3O+ 3) LDA
2) EtLi / H3O+ 3) LDA
3
Problem
ProblemPropose a synthesis:
A
1) Cl2
2) CH3ONa (excess) 3) CH3Br
4) H2/Pt
2) CH3ONa (excess) 3) CH3Br
4) H2/Pt
B
1) O3, Me2S
2) EtLi / H3O+ 3) LDA
2) EtLi / H3O+ 3) LDA
C
1) Br2
2) NaNH2 (2 eq.) 3) H3O+/H2O
4) CH3MgBr / H3O+
2) NaNH2 (2 eq.) 3) H3O+/H2O
4) CH3MgBr / H3O+
D
1) Br2
2) NaNH2 (excess) 3) CH3I
4) Na/Liq. NH3
2) NaNH2 (excess) 3) CH3I
4) Na/Liq. NH3
4
Problem
ProblemA
1) Br2 / Δ
2) LDA 3) Br2
4) NaNH2 (2 eq.) 5) H3O+/H2O
6) EtMgBr / H3O+
2) LDA 3) Br2
4) NaNH2 (2 eq.) 5) H3O+/H2O
6) EtMgBr / H3O+
B
1) Br2 / Δ
2) LiTMP 3) Br2
4) NaNH2 (2 eq.) 5) O3, Me2S
6) CH3CH2CH2MgBr
2) LiTMP 3) Br2
4) NaNH2 (2 eq.) 5) O3, Me2S
6) CH3CH2CH2MgBr
C
1) Br2 / Δ
2) KOC(CH3)3 3) Br2
4) NaNH2 (excess) 5) CH3CH2I
6) H2/Pt
2) KOC(CH3)3 3) Br2
4) NaNH2 (excess) 5) CH3CH2I
6) H2/Pt
D
1) Cl2 / Δ
2) NaH 3) Br2
4) NaNH2 (2 eq.) 5) KMnO4, OH-, Δ / H+ 6) CH3CH2CH2MgBr
2) NaH 3) Br2
4) NaNH2 (2 eq.) 5) KMnO4, OH-, Δ / H+ 6) CH3CH2CH2MgBr
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