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2 xs HX 1 X 1) xs NaNH2 2) H₂O R R 3 4 5 -CH3 R R H HgSO4 H2SO4, H₂O 1) R₂BH HX X2 (one equiv.) 2) H2O2, NaOH X R CCl4 6 R X X 1 1) xs NaNH2 XS X2 X X X R 2) H₂O 1) NaNH2 2) RX 1) O3 2) H₂O CCl4 X R 7 9 8 H2 12 R R R R Lindlar's cat. + R OH O=C=0 H₂ Na R R 10 11 R Pt NH3 (1) R

2 xs HX 1 X 1) xs NaNH2 2) H₂O R R 3 4 5 -CH3 R R H HgSO4 H2SO4, H₂O 1) R₂BH HX X2 (one equiv.) 2) H2O2, NaOH X R CCl4 6 R X X 1 1) xs NaNH2 XS X2 X X X R 2) H₂O 1) NaNH2 2) RX 1) O3 2) H₂O CCl4 X R 7 9 8 H2 12 R R R R Lindlar's cat. + R OH O=C=0 H₂ Na R R 10 11 R Pt NH3 (1) R

Chemistry for Today: General, Organic, and Biochemistry
Chemistry for Today: General, Organic, and Biochemistry
9th Edition
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Chapter18: Lipids
Section: Chapter Questions
Problem 18.18E
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Plan a synthesis of cis-3-hexane using acetylene as your only source of carbon atoms.

2 xs HX 1 X 1) xs NaNH2 2) H₂O R R 3 4 5 -CH3 R R H HgSO4 H2SO4, H₂O 1) R₂BH HX X2 (one equiv.) 2) H2O2, NaOH X R CCl4 6 R X X 1 1) xs NaNH2 XS X2 X X X R 2) H₂O 1) NaNH2 2) RX 1) O3 2) H₂O CCl4 X R 7 9 8 H2 12 R R R R Lindlar's cat. + R OH O=C=0 H₂ Na R R 10 11 R Pt NH3 (1) R
Transcribed Image Text:2 xs HX 1 X 1) xs NaNH2 2) H₂O R R 3 4 5 -CH3 R R H HgSO4 H2SO4, H₂O 1) R₂BH HX X2 (one equiv.) 2) H2O2, NaOH X R CCl4 6 R X X 1 1) xs NaNH2 XS X2 X X X R 2) H₂O 1) NaNH2 2) RX 1) O3 2) H₂O CCl4 X R 7 9 8 H2 12 R R R R Lindlar's cat. + R OH O=C=0 H₂ Na R R 10 11 R Pt NH3 (1) R
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