Documente Academic
Documente Profesional
Documente Cultură
Nomenclature!
" Alcohols are named using the same procedure we used in Chapter 4 to name alkanes with minor modications:! 1." 2." 3." 4." 5." Identify the parent chain, which should include the carbon that the OH is attached to.! Identify and name the substituents.! Assign a locant to each substituent. Give the carbon that the OH is attached to the lowest number possible.! List the numbered substituents before the parent name in alphabetical order. Ignore prexes (except iso) when ordering alphabetically.! The OH locant is placed either just before the parent # name or just before the -ol sufx.!
Nomenclature!
" Alcohols are named using the same procedure we used in Chapter 4 to name alkanes with minor modications:! 1." 2." 3." 4." 5." Identify the parent chain, which should include the carbon that the OH is attached to! Identify and name the substituents.! Assign a locant to each substituent. Give the carbon that the OH is attached to the lowest number possible.! List the numbered substituents before the parent name in alphabetical order. Ignore prexes (except iso) when ordering alphabetically.! The OH locant is placed either just before the parent # name or just before the -ol sufx.!
Nomenclature!
Nomenclature!
1 !
Nomenclature!
Nomenclature!
Nomenclature!
For cyclic alcohols, the OH group should be on carbon 1, so often the locant is assumed and omitted.! !
Nomenclature!
Nomenclature!
When an OH group is attached to a benzene ring, the parent name is PHENOL.! !
Physical Properties!
2 !
2. Alkali metals!
3 !
"
"
4 !
"
"
"
For oxidation states, we imagine the bonds breaking heterolytically, and the electrons go to the more electronegative atom.!
"
For oxidation states, we imagine the bonds breaking heterolytically, and the electrons go to the more electronegative atom.!
"
For oxidation states, we imagine the bonds breaking heterolytically, and the electrons go to the more electronegative atom.!
vs.!
"
For oxidation states, we imagine the bonds breaking heterolytically, and the electrons go to the more electronegative atom.!
5 !
Reducing Agents!
" "
Calculate oxidation states of the carbonyl carbon.! Is the reducing agent oxidized or reduced?!
Reducing Agents!
There are three reducing agents you should know:! Reagents that can donate a HYDRIDE are generally good reducing agents:! 2. Sodium borohydride!
"
Reducing Agents!
There are three reducing agents you should know:! Reagents that can donate a HYDRIDE are generally good reducing agents:! 2. Sodium borohydride!
Reducing Agents!
There are three reducing agents you should know:! Reagents that can donate a HYDRIDE are generally good reducing agents:! 3. Lithium Aluminum Hydride (LAH)! : LAH is signicantly more reactive that NaBH4.! !
6 !
Reducing Agents!
There are three reducing agents you should know:! Reagents that can donate a HYDRIDE are generally good reducing agents:! 3. Lithium Aluminum Hydride (LAH)! : LAH is signicantly more reactive that NaBH4.! ! !
Reducing Agents!
There are three reducing agents you should know:! Reagents that can donate a HYDRIDE are generally good reducing agents:! 3. Lithium Aluminum Hydride (LAH)! : LAH is signicantly more reactive that NaBH4.!
Reducing Agents!
" HYDRIDE delivery agents will somewhat selectively reduce carbonyl compounds.! !
Reducing Agents!
" LAH is significantly more reactive that NaBH4. As a result, LAH is less selective. " LAH is strong enough to also reduce esters and carboxylic acids, whereas NaBH4 is generally not. !
Reducing Agents!
" LAH is significantly more reactive that NaBH4. As a result, LAH is less selective. " LAH is strong enough to also reduce esters and carboxylic acids, whereas NaBH4 is generally not. !
Reducing Agents!
" Mechanism!
7 !
Reducing Agents!
" Mechanism!
Reducing Agents!
" Mechanism!
Preparation of Diols!
" Reducing Agents!
Preparation of Diols!
" Oxidizing Agents!
8 !
" "
The carbon atom is not able to effectively stabilize the negative charge it carries.! It act as an nucleophile.!
" "
The carbon atom is not able to effectively stabilize the negative charge it carries.! It act as an nucleophile.!
9 !
Protection of Alcohols!
10 !
Protection of Alcohols!
Protection of Alcohols!
" " Evidence suggests that substitution at the Si atom occurs by an SN2 mechanism.! Because Si is much larger than C, it is more open to backside attack.!
Protection of Alcohols!
Protection of Alcohols!
via SN1!
11 !
"
"
"
12 !
! !
13 !
2. Elimination of activator!
14 !
! ! ! !
Oxidation of Phenol!
" " Recall that tertiary alcohols do not undergo oxidation because they lack an alpha proton.! You might expect phenol to be similarly unreactive.!
! " Yet, phenol is even more readily oxidized than primary or secondary alcohols.!
! " Yet, phenol is even more readily oxidized than primary or secondary alcohols.!
15 !
16 !