Page1 / 28

11_all_ - 11.1 What is wrong with the use of such names as...

This preview shows document pages 1 - 6. Sign up to view the full document.

View Full Document Right Arrow Icon

11_all_ - 11.1 What is wrong with the use of such names as...

Info iconThis preview shows pages 1–6. Sign up to view the full content.

View Full Document Right Arrow Icon
11.1 What is wrong with the use of such names as “isopropanol” and “tert-butanol”? Answer: We should say them as “isopropyl alcohol” and “tert-butyl alcohol”. 11.2 Give bond-line formulas and appropriate names for all of the alcohols and ethers with the formulas (a) C 3 H 8 OH and (b) C 4 H 10 O (a) CH 3 CH 2 CH 2 OH propanol H 3 CC H CH 3 OH 2-propanol CH 3 OCH 2 CH 3 Ethyl methyl ether (b) CH 3 CH 2 CH 2 CH 2 butanol H 3 C H 2 C C H OH CH 3 2-butanol CO H H 3 C H 3 C H 3 C tert-butyl alcohol CH 3 OCH 2 CH 2 CH 3 propyl methyl ether CH 3 CH 2 OCH 2 CH 3 diethyl ether H 3 H CH 3 OCH 3 isopropyl methy ether OH 2-methyl-1-propanol 11.3 1,2-Propanediol and 1,3-propanediol(propylene glycol and trimethylene glycol, respectively; see Table11.2)have higher boiling points than any of the butyl alcohols, even though all of the compounds have roughly the same molecular weight. How can you explain this observation. The diols have two –OH, so it can form stronger hydrogen bonding. Therefore, 1,2-Propanediol and 1,3-propanediol have higher boiling points than any of the butyl alcohols. 11.4 What products would you expect from acid-catalyzed hydration of each of the following alkene? (a) Ethene (c)2-Methylpropene (b)Propene (d)2-Methyl-1-butene (a) H 3 O OH
Background image of page 1

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

View Full DocumentRight Arrow Icon
(b) H 3 O OH (c) H 3 O OH (d) H 3 O HO 11.5 Treating 3,3-dimethyl-1-butene with dilute sulfuric acid is largely unsuccessful as a method for preparing 3,3-dimethyl-2-butanol because an isomeric compound is the major product. What is this isomeric compound and how is it formed? 3,3-dimethyl-1-butene H OH 2,3-Dimethyl-butan-2-ol (main) 11.6 Starting with an appropriate alkene, show all steps in the synthesis of each of the following alcohols by oxymercuration-demercuration. (a) tert-Butyl alcohol (b) Isopropyl alcohol (c) 2-Methyl-2-butanol Answer: (a) tert-butyl alcohol (1) Hg(OAc) 2 /THF-H 2 O (2) NaBH 4 ,OH (b)
Background image of page 2
HO Isopropyl alcohol (1) Hg(OAc) 2 /THF-H 2 O (2) NaBH 4 ,OH (c) HO 2-Methyl- 2-butanol (1) Hg(OAc) 2 /THF-H 2 O (2) NaBH 4 ,OH 11.7 When an alkene is treated with mercuric trifluoroacetate, Hg (O2CCF3)2, in THF containing an alcohol, ROH, the product is an (alkoxyalkyl) mercury compound. Treating this product with NaBH4/OH- results in the formation of an ether. The overall process is called solvomercuration-demercuration. Hg(O 2 CCF 3 ) 2 /THF-ROH solvomercuraton RO HgO 2 CCF 3 NaBH 4 ,OH - demercuraton H OR Alkene (Alkoxyalkyl)mercuric trifluoroacetate Ether a) Outline a likely mechanism for the solvomercuration step of this ether synthesis. b) Show how you would use solvomercuration-demercuration to prepare tert-butyl methyl ether. a) Step 1:
Background image of page 3

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

View Full DocumentRight Arrow Icon
O O F F F + O O F F F O O F F F Hg O O F F F Hg Step 2: Hg O O F F F Hg O O F F F δ δ Step 3: Hg O O F F F Hg O O F F F OH R R OH R OH Hg O O F F F OH δ δ Step 4(demercuration):
Background image of page 4
Hg O O F F F OH H NaBH 4 , OH - b) The reaction is: Hg(O 2 CCF 3 ) 2 /THF-CH 3 OH solvomercuraton O HgO 2 CCF 3 NaBH 4 ,OH - demercuraton O 11.8 Starting with an appropriate alkene, show the synthesis for (a) tributylborane, (b) triisobutylborane, and (c) tri-sec-butylborane. (d) Show the stereochemistry involved in the hydroboration of 1-methylcyclohexene.
Background image of page 5

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

View Full DocumentRight Arrow Icon
Image of page 6
This is the end of the preview. Sign up to access the rest of the document.
Ask a homework question - tutors are online