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;
28 Cards in this Set
- Front
- Back
|
alkyl halide
|
RCl
|
|
|
amine
|
RNH2
|
|
|
epoxide
|
C-O-C triangle
|
|
|
ether
|
R-O-R
|
|
|
nitrile
|
C-triple bond-N
|
|
|
nitroalkane
|
RNO2
|
|
|
thiol
|
RSH
|
|
|
aldehyde
|
R(C=O)H
|
|
|
ketone
|
R(C=O)R
|
|
|
carboxylic acid
|
R(C=O)OH
|
|
|
acyl halide
|
R(C=O)X
|
|
|
acid anhydride
|
R(C=O)O(C=O)R
|
|
|
ester
|
R(C=O)OR
|
|
|
amide
|
R(C=O)NR2
|
|
|
tetrahydrofuran
|
pentane ring with one carbon replaced by oxygen
|
|
|
pyrrolidine
|
pentane ring with one carbon replaced by nitrogen-hydrogen
|
|
|
piperidine
|
hexane ring with one carbon replaced by nitrogen-hydrogen
|
|
|
Three ways to convert alcohols to alkyl halides
|
1. add HX (halogen halide) to form RX plus H2O
2. add SOCl2 (thionyl chloride) to form RX + SO2 + HCl 3. add PBr (phosphorus tribromide) to form 3RBr + H3PO3 |
|
|
vinyl
|
CH2=CH-R
|
|
|
allyl
|
CH2=CHCH2-R
|
|
|
isopropenyl
|
CH2=C(CH3)-R
|
|
|
methylene
|
CH2 group double bonded to ring
|
|
|
Dehydration of alcohols
|
acid catalyst
order of reactivity=tert, second, primary for stability rearrangement |
|
|
Dehydrohalogenation of alkyl halides
|
strong base
adjacent proton and halide halide reactivity order anti periplanar transition state most stable no rearrangement because no carbocation intermediate |
|
|
dehydation of alcohols
|
step 1: alcohol protonated
step 2: alklyoxonium ion leaves creating carbocation intermediate step 3: adjacent carbon to carbocation carbon is deprotonated |
|
|
carbocation rearrangement types (2)
|
1) alkyl group migration
2) hydride shift |
|
|
E2 mechanism
|
concerted process: base removes proton from beta carbon while halide-alpha carbon bond undergoes heterolytic cleavage and double bond forms.
|
|
|
E1 mechanism
|
unimolecular: ionizatio of alkyl halide to carbocation is rate determining step. Is followed by deprotonation of the carbocation.
|
