chpater9-11-worksheet_ans.cdx

chpater9-11-worksheet_ans.cdx - product is propyne. Give...

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Chapters 9 and 11 Synthesis and Mechanisms Worksheet 1. Starting with acetylene, and using any needed reagents, show how the compounds below could be synthesized. For any chiral product, assumed it's produced as a racemic mixture (a) D D H (b) H 3 C CH 2 CH 2 CH 3 (c) C C H CH 3 Et H HO OH (d) (degree of difficulty =10) HC CH 1) NaNH 2 2) Br C CH D 2 Lindlar's Pd D D H HC CH 1) NaNH 2 HC CH 1) NaNH 2 HC CH 1) NaNH 2 2) CH 3 I CH 3 C CH 1) NaNH 2 2) CH 3 CH 2 CH 2 I CH 3 C CCH 2 CH 2 CH 3 Li NH 3 CH 2 I 2 Zn(Cu) C C D H H 3 C H CH 3 CH 2 O Br 2) CH 3 I CH 3 C CH 1) NaNH 2 2) CH 3 CH 2 Br CH 3 C CCH 2 CH 3 C C H Et HO OH CH 3 H Lindlar's Pd H 2 OsO 4 H 2 O 2 2) CH 3 I CH 3 C CH 1) 9-BBN-d / THF 2)CH 3 CH 2 CO 2 H C C H H D H 3 C Br 2 ethanol
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(e) Br 2. Mechanism questions: use mechanistic notation to answer the following. Place the mechanistic notation is the correct chronological sequence. (a) The reaction of ethyl magnesium bromide with acetaldehyde followed by acidic work-up is best described by these two mechanistic steps: (b) Sodium metal reduction of 3-hexyne to form E-3-hexene goes by these four steps. Circle the step responsible for the E-geometry. (c) When acetylide is first reacted with sodium amide and the resulting solution is treated with methyl iodide, the
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Unformatted text preview: product is propyne. Give the mechanistic notation for this two step process. (d) When a terminal alkyne is place in water with sulfuric acid and HgSO 4 a methyl ketone is produced. Write the notation for the first three steps. 3. You have three types of ethanols in your lab: unlabeled ethanol, ethanol labeled with 13 C at carbon #1 and ethanol labeled at with 13 C at carbon #2. Show how the ketone below could be synthesized using only the aforementioned ethanols as your only carbon sources. 13 CH 3 CH 2 CCH 3 O HC CH 1) NaNH 2 2) Br C CH HBr, 1 eq. A N π PT A R π A R π PT PT PT S N 2 A E π A N + PT 13 CH 3 CH 2 OH PBr 3 13 CH 3 CH 2 Br 1) Mg, ether 3) H 3 O + 13 CH 3 CH 2 CHCH 3 OH Na 2 Cr 2 O 7 H 2 SO 4 (aq) 2) CH 3 CH O CH 3 CH 2 OH PCC CH 2 Cl 2...
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This note was uploaded on 09/03/2009 for the course CHEM 2250 taught by Professor Stack during the Spring '09 term at UNO.

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chpater9-11-worksheet_ans.cdx - product is propyne. Give...

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