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Prelim 2
ch8-10
31
Chemistry
Undergraduate 2
11/14/2013

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Term
3 solvent prop
Definition
bronsted
lewis
polarity
Term
2 bronsted prop
Definition
1. protic (H bond donor)
2. Aprotic (no h bond donor)
Term
lewis prop
Definition
1. donor (good lewis base)
2. nondonor (no lewis base prop)
Term
polarity Prop
Definition
1. polar
2. nonpolar
Term
Polar, protic solvents
Definition
H20
CH3OH
EtOH (alcohols)
HCONH2
excellent anion and cation stab
Term
polar aprotic solvents
Definition
DMF
DMSO
HMPA
CH3CN
excellent cation stab
very reactive nuc
Term
nonpolar protic sovlents
Definition
acetic acid
good cation and anion stab
Term
nonpolar, aprotic, donor solvents
Definition
ether
THF
1,4 dioxane
good cation stab
Term
nonpolar, aprotic, nondonor solvents
Definition
alkane
CH2Cl2
CHCl2
Benzene
no cation or anion stabilization
Term
solvation does what to bronsted acidity
Definition
enhance
stabilize
Term
strongest acid that can exist in any solvent is...
Definition
conjugate acid of that solvent itself
Term
same row basicity/nuc
Definition
nuc up as basicity up
Term
same column nuc/basicitiy
Definition
nuc up as basicity down
Term
Sn2 prefers ____ solvent
Definition
protic > aprotic
Term
in E2, what wins, Zaitsev or anti?
Definition
anti
Term
What is Sn2 favored by
Definition
1. strong nuc (and weak base)
2. Solvent choice
Term
What is Sn2 slowed by
Definition
1. a, b C branching
2. bulky, branched nuc
Term
Sn1, E1 what prime alkyl halide
Definition
3 prime
Term
Sn1, E1 solvents
Definition
polar, protic, donor solvents
alcohols, formic acid, mixture of H20 with alkyl halide soluble
Term
Sn1 stereochemically selective?
Definition
No, unlike Sn2, form sp2 carbocation achiral planar intermediate, which leads to a racemic mixture
Term
2 prime alkyl halides, what reactions possible
Definition
Sn1, E1, Sn2, E2
Term
Favor Sn2, E2 during 2 prime alkyl halide rxns
Definition
polar, aprotic, solvent
Term
favor E1, Sn1 during 2 prime alkyl halides
Definition
polar, protic solvent
Term
simmons smith rxn
Definition
ch2I2 zn-Cu in either
concerted syn addition
carbene
Term
cl2C:
Definition
a elimination
stereochemically preserved
Term
directed cycloproponation
Definition
only forms on side with O:-
Term
ways to make alcohol better leaving group
Definition
protonation (alkyl halide, acid)
TsCl or MsCl in pyridine (retention)
thionyl chloride inversion
PBr3 inversion
Term
1 prime alcohol to aldehyde, ketone
Definition
pcc Ch2Cl2
anhydrous
Term
1 prime alcohol into ketones and carboxylic acids
Definition
CrO3 in H2O
aq conditions
KMnO4
K2Cr2O7
Term
RSH + KMnO2 or HNO3
Definition
sulfonic acid
Term
2RSH+ Br-Br
Definition
RS-RS
disulfides
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