alcoholsg - Alcohols 1 Copyright, Arizona State University...

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

View Full Document Right Arrow Icon

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

View Full DocumentRight Arrow Icon

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

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

Unformatted text preview: Alcohols 1 Copyright, Arizona State University Copyright, Arizona State University Alcohols Oxidation and Reduction (more...) 1 Nomenclature Notation, recall.... R C OH R C R C OH R' R'' R' OH 1 o , primary 2 o , secondary 3 o , tertiary H H H IUPAC naming priority, alcohol > alkene ~ alkyne > halide (more oxidized functional groups have higher priority) suffix: -ol OH phenol CH 3 OH CH 2 OH CH 3 methanol ethanol HO 1 2 3 4 5 (2S,5)-dimethylhept-(4E)-en-1-ol HO 1 2 3 4 5 6 7 6-methyl-3-propyl-2-heptanol sterochemistry ignored 6 7 note the use of number directly before the functional group in the example on the right, used when we have multiple functional groups Some Common Alcohols with Common Names: (I won't test you on these!) . OH HO OH glycerol HO OH ethylene glycol OH benzyl alcohol OH iso-propanol 2 Alcohol Acidity, Return to Substituent Effects (more...) Alcohols are weak acids, the -OH bonds are similar to those in water unless the conjugate base anion is stabilized by a specific effect, such as resonance OH OH H 2 O H 2 O O O ~19.0 ~9.0 pKa O O O cyclohexanol phenol + H 3 O + the energy of the non-bonding electrons in the conjugate base anion of phenol are lower compared to cyclohexanol due to resonance delocalization/stabilization, phenol is the stronger acid, has the smaller pKa Alcohols 2 Copyright, Arizona State University Copyright, Arizona State University Alcohol PROBLEMS Alcohol Nomanclature Provide a IUPAC name for each of the following (ignore stereochemistry unless specified) 1 (standard) OH Answer Correct Y / N 2 (standard) OH OH Answer Correct Y / N 3 (standard) OH Answer Correct Y / N 4 (standard) OH Answer Correct Y / N 5 (standard) OH OH Answer Correct Y / N 6 (standard) OH Answer Correct Y / N 7 (standard) OH Answer Correct Y / N 8 (standard) HO Answer Correct Y / N 9 (standard) OH Answer Correct Y / N 10 (standard) H Br H HO Answer Correct Y / N 11 (standard) OH Answer Correct Y / N UNDERSTANDING is different from DOING. In each of the above scenarios you have not proven that you can do the problem, rather you have proven that you CAN'T do the problem without help from others, or without "cheating" on the time it takes to do a problem, or without proving that you can do the problem 100% correct. Alcohols 3 Copyright, Arizona State University 2.1 Review of Substituent Effects Remember : There are TWO kinds of substituent effects, INDUCTIVE and RESONANCE , and in the context of alcohol acidity we also need to consider solvent effects Simple alcohols have roughly similar acidity to water that can be altered by alkyl SUBTITUENT EFFECTS Extra methyl groups weakly donate electrons towards the anion (remember alkyl stabilization of carbocations and destabilization of carbanions) H 3 C CH H 3 C OH ~19.0 H 3 C CH H 3 C O H 2 O + H 3 O + Me- donating groups weakly destabilize anion and LOWER solvation of the anion CH 3 CH 2 OH ~15.9 CH 3 CH 2 O H 2 O + H 3 O + H 2 O CH 3 OH pKa ~15.5 ~15.5~15....
View Full Document

Page1 / 17

alcoholsg - Alcohols 1 Copyright, Arizona State University...

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