Test 1 - O chem 2 Flashcards
RCOR’
ketone
ROH
alcohol
RCOOH
carboxylic acid
RSH
thiol
ROR
ether
ROCH
aldehyde
RCOOR
ester
RSR
sulfide
which is more reactive, alcohols or ethers
alcohols
which is more reactive, aldehydes or ketones
aldehydes
origins of ketones
G. Aketon
origins of aldehydes
alcohol dehydrogenated
origins of alcohol
A. al kuhl
origins of ether
L. aether
origins of ester
G. essigaither
alpha carbon
carbon bonded to X
beta carbons
one away from alpha
MUST have H atom bonded to it
carbocations are carbon atoms making _____ bonds
3
carbocations are ____ and ___________________
flat, trigonal planar
carbocation bond angle
120
how do carbocations form
heating alkyl-halides or acidifying alcohols
carbocation stability
3 > 2 > 1 > methyl
what degree of carbocation is most stable
why?
3rd
due to alkyl induction
is a carbocation has a DB, it has the stability of a ____
1st degree
allylic (resonance) carbocations have
+ charge
a shared DB
carbocation rearrangement requirements
1st or 2nd degree C+
beta branching
alkene stability
tetra-sub > tri-sub > di-sub > mono-sub > ethylene
E2 favorite bulky base
KOtBu
alkenes as E2 reaction products
number of beta H’s = number of products
new alpha - beta bond
zaitsev and hoffman products
zaitsev vs hoffman products
zaitsev = major (80%), higher substitution of beta carbons
horroman = minor (20%), lower substitution of beta carbons
when to use cis/trans vs Z/E
cis/trans: when chains are identical on either side of DB
Z/E: when chains are NOT identical on either side of DB
cis/trans
cis: on the same side
trans: on opposite sides
Z/E
Z: on the same side
E: on the same side
1st degree alkyl halide reaction types
Sn2 only
2nd degree alkyl halide reaction types
Sn2, E2, Sn1, E1
ALL OF THEM
3rd degree alkyl halide reaction types
E2, Sn1, E1
base structure, mechanism, and reaction type
bulky
pluck off H atom
E2 reactions
nucleophile structure, mechanism, and reaction type
not bulky (linear/have DBs)
attack and connect to partial + C atoms
Sn2 reactions
E1 reactions have ____________ curly arrows
3
in E1 reactions, if carbocation is 1st or 2nd degree, you should __________________
attempt rearrangement (~H/~R)
steps for alkene nomenclature
- number main chain starting closest to DB (main chain MUST include DB)
- DB should be lowest number (takes higher priority than branching)
- classify alkene as cis, trans, E, or Z
4 types of nucleophiles
A:
A:-
A = A
A (triple bond) A
addition reaction reaction rate based on substitution
tetra > tri > di > mono
why are tetra-substituted alkenes fastest in addition reactions
alkyl induction
curly arrows start at
e- location
syn vs trans
syn: both new groups on same side of former DB
trans: new groups on opposite side of former DB
what stereochemical classifications give a +1
cis alkenes
syn addition
meso products
what stereochemical classifications give a -1
trans alkene
anti addition
D, L products
markonikov product
H rich alkenyl atom becomes MORE H rich
(antiM product is opposite)
hydration reaction fastest reaction alkene
tetra substituted
what is the product of an alkene hydration reaction
alcohols
in the first step of alkene hydration reactions, what side is protonated and what side is designated with a +
least substituted side is protonated
most substituted side is designated +
the product of a alkene hydration reaction is
neutral
stable carbocations are
more highly substituted
what degree of alcohol does NOT receive oxidation
3rd degree
oxidation of alcohols = an increase in __________ and a decrease in ___________
C-O bonds, C-H bonds
weak oxidizing agent
PCC
3 oxygen atoms
strong oxidizing agent
Na2Cr2O7/H2SO4
(22724)
11 oxygen atoms
PCC on 1st degree alcohol
increases number of C-O bonds by ONE
Na2Cr2O7/H2SO4 on 1st degree alcohol
replaces ALL C-H bonds with C-O bonds
oxidizing agents on 2nd degree alcohols
same product regardless of oxidating agent
ozonolysis
splitting of a DB using O3
alkenes are _____________, therefore they are considered _____________
electron rich, nucleophiles
