Reading...
Play button
Play button
Use LEFT and RIGHT arrow keys to navigate between flashcards;
Use UP and DOWN arrow keys to flip the card;
H to show hint;
A reads text to speech;
19 Cards in this Set
- Front
- Back
|
Solubility of alcohols
|
OH group is hydrophilic, while carbon chain is hydrophobic
Less soluble as alcohol adds more carbons Phenol soluble because of round shape; in general, cyclo structures more soluble More OH groups, more soluble Enantiomers=identical solubility |
|
|
How # of carbons in alcohol changes solubility
|
Between 1-4 carbons, miscible
Between 5 and 10 carbons, varying degree of solubility More than 11 carbons=insoluble |
|
|
Densities of alcohols
|
.8-.9 g/mL; density of water is 1.00 g/ml
|
|
|
Boiling points of alcohols
|
High boiling points compared to alkanes, alkenes, alkynes, ethers (due to hydrogen bonding...when H is bonded to N, O or F. Also due to electrostatic intermolecular force (dipole-dipole)).
Ether has lower BP (pure ether not capable of H bonding to molecules), but alkane/ene/yne the lowest |
|
|
Energy in OH bond
|
Energy of OH grp=2-7 kCal/mol or 8-30 KJ/mol
|
|
|
Basic acidities of alcohols
|
Less acidic or equal to acidity of water
Acidity goes down as substitution goes up R--O--H is weak, so plus a strong basegives an R--O- ion Phenol WAAAAAAYYYY more acidic (10^8 times more) than cyclohexanol bc of resonance |
|
|
Numerical acidities (pka values) of alcohols
|
R--O--H, the H has a pKa of 15-18
H--O--H, pka is 15.7 Ph--OH, pka of H is 10 |
|
|
Inductive effects (halogens on acidity of alcohols)
|
Halogens, since electron withdrawing, help stabilize and increase acidity by balancing e- out; larger partial positive...do this through INDUCTIVE EFFECTS (the donation or withdrawal of electron density through sigma bonds)
More electronegative halogen (F>Cl>Br>I)=more stabilized, higher acidity |
|
|
What are Grignards incompatible with?
|
(Can't have the following in self or solvents)
WATER Will attack: OH, NH, SH, =C triple bond CH because Grignard will protonate them Will be attacked by: C=O, C triple bond N, C=N:, S=O, N=O |
|
|
What do Grignards react well with?
|
Grignards react well with aldehydes, ketones, epoxides and esters (if they have two moles of the grignard)
|
|
|
What is a diol?
|
Alcohol with two OH grps
(1,2) diol is a glycol |
|
|
Priority for nomenclature--numbering for the three groups we've studied?
|
Alcohols, then alkene, then alkyne
|
|
|
Catechol
|
Benzene ring with two OH grps on adj carbons
(aka ortho-phenol) |
|
|
Resorcinol
|
Benzene ring with 1, 3 OH grps
(aka meta-phenol or cresol) |
|
|
Hydroquinone
|
Benzene ring with 1, 4 OH grps
(aka para-phenol) |
|
|
alkoxide ion
|
R--O- formed by deportation
|
|
|
hydroxy group
|
--OH group
|
|
|
ether
|
R--O--R
|
|
|
ester
|
R--C(=O)O--R
|
