Identify the reagents necessary to accomplish the following steps in the product
ID: 556030 • Letter: I
Question
Identify the reagents necessary to accomplish the following steps in the production of: (3R, 4S)-3,4-dibromohexane from acetylene. 7 pr 1 pt Cl HC CH 10 1 pt HC CH HC-CH 12 1pt HC CH 4 1pt Reagents available 7 pt a. HCl e. H2, Pd b. HBr .Os04 then NaHSOs . Na/NH c. Br g.Os then (CHs)2S d. Cl2 h. 2 equivalents of NaNH2 1.1 equivalent of NaNH2 i. H2/Lindlar's catalyst k. (sia)2BH then H202, NaOH The above synthesis scheme was designed using the Organic Chemistry Roadmaps in the appendix of your textbook In this scheme, identify the reagents necessary to accomplish the following steps in the production of (3R.4S)-3,4-dibromohexa 4 at Step 5Explanation / Answer
1) i) H2, Lindlard's catalyst
2) b) HBr
3) l) 1 equivalent of NaNH2
4) a) HCl
5) e) H2, Pd
6) l) 1 equivalent of NaNH2
Explanation: reduction of alkyne with H2, Lindlard's catalyst produces alkene as product. Addition of HBr to alkene produces alkyl halide as product. NaNH2 is a strong base which abstracts acidic proton and produces acetylide ion.