Week 7thurs-key - 6. How would you synthesize the following...

Info iconThis preview shows pages 1–4. Sign up to view the full content.

View Full Document Right Arrow Icon
Week 7-Thurs CEM 251 recitation nguye143@msu.edu 1. Draw structures corresponding to the following names: a. 2,2,5,5-tetramethyl-3-hexyne b. 3-ethyl-5-methyl-1,6,8-decatriyne c. 3-chloro-4,4-dimethyl-1-nonen-6-yne Cl 2. Predict the products of the following reactions: H 2 , Pd/C H 2 / Lindlar's catalyst Make sure you indicate the bond is cis or trans by drawing it that way. The following is NOT an acceptable answer. 3. Predict the products from reaction of 1-hexyne with the following reagents: a. H 2 , Lindlar catalyst 1-hexene b. 1 equiv Br 2 (E)-1,2-dibromohex-1-ene
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
c. H 2 O, H 2 SO 4 , HgSO 4 O d. Li in NH 3 (Usually gives trans double bond, however, is not applicable with 1- hexyne) e. BH 3 in THF, then H 2 O 2 , OH - O H 4. What reagent would you use to get the following products? O O H H 2 O, H 2 SO 4 HgSO 4 1)BH 3 in THF 2)H 2 O 2 , OH - 1) NaNH 2 2) CH 3 -X (Br or I) Li in NH 3
Background image of page 2
5. How would you synthesize the following molecules from given starting materials. (You will need more than one step). H H O H 1) NaNH 2 2) CH 3 CH 2 Br 3) Li in NH 3 1) NaNH 2 2) CH 3 Br 3) CH 2 I 2 , Zn(Cu) 1)BH 3 in THF 2)H 2 O 2 , OH -
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 4
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: 6. How would you synthesize the following compounds using only acetylene and any alkyl halides with four or fewer carbons? More than one step may be needed. a. 1-pentyne b. 3-hexyne c. 4-octanone d. 1-hexanal 7. Compound A (C 9 H 12 ) absorbed 3 equivalents of H 2 on catalytic reduction over a palladium catalyst to give B (C 9 H 18 ) *calculate RDBs, B still has one even after H 2 /Pd-we know B has a ring, so A does also* . On ozonolysis, compound A gave, among other things, a ketone that was identified as cyclohexanone * If ozonolysis give us a ketone, we have an alkene, so there is 1 double bond and 1 ring, the other 2 sites of unsaturation are 1 triple bond* . On treatment with NaNH 2 in NH 3 , followed by addition of iodomethane, compound A gave a new hydrocarbon, C (C 10 H 14 ) *still has the same number of RDBs, we only add a methyl group* . What are the structures of A, B, and C?...
View Full Document

This note was uploaded on 12/02/2008 for the course CEM Cem 251 taught by Professor Tepe during the Fall '08 term at Michigan State University.

Page1 / 4

Week 7thurs-key - 6. How would you synthesize the following...

This preview shows document pages 1 - 4. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online