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128 Cards in this Set

  • Front
  • Back
pi and sigma bond
which is stronger?
sigma bond
additio of protic acid (H+) to an alkene occurs such that the proton attaches to th carbon atom w/ akyl group producing mst stable carbocation. (proton will be added to he carbon w the greatest # of hydrogen)
markovnikov rule
ROOR
peroxides
H2SO4

strong or week acid?
strong acid
alcohol and strong acid like H2SO4 lead to?
elimination rxn
DMSO is protic or aprotic?
aprotic
X is added to least substituted carbon of double bond. free radical additon occurs when peroxides, oxygen, uv light or other adicalcusing codtion are present
antimarkovnikov addition
X2 (halogen like Br or Cl)to alkene
anti addition of halogens

alkene to alkane
NH2-
strong base
H2/Pt
alkene or alkyne to alkane in syn addition of H2
alkene or alkyne to alkane in syn addition of H2
H2/Pt
H2, Pd/BaSO4 and quinline (lindlar's catalyst)
alkyne to cis alkene
2 butyne to cis 2 butene
alkyne to cis alkene
2 butyne to cis 2 butene
H2, Pd/BaSO4 and quinline (lindlar's catalyst)
Na, NH3 (liq)
alkyne to trans alkene

2 butyne to trans 2 butene
alkyne to trans alkene

2 butyne to trans 2 butene
Na, NH3 (liq)
primary halide (CCOH) favors
SN2
second and third halide favors
E2 rxn due to steric hinderance
inc in temp also favors ??
elimination over substitution

b/c more bonds are broken and formed in elimination and inc temp inc rate
strong and bulky base is favored in
E2 rxn
large pka =
dec acidity = inc in base (stronger the base)
E2 rxn favors most or lest substitutted double bond
most subsitutted
alkyl halides to dehydrogenation, you often get multiple product
double with most sub and lest sub molecule
zaitsev's rule
more stable base such as ethoxide ion when dehydrogenation you often get more stable double bond molecule whichis
most substituted =more stable
bulky bse favors more or less sub double bond molecule?
less sub
when elimination yield the less substituted alkene we say that it followed
hoffmann rule
the overal relative ease with which alcohols undergo dehydration ?
tertiary alcohol>secondary alcohol> primary alcohol
in radical rxn, Br is more () than Cl

Cl is mor () than Cr
selective (make more stable form)

reacive (mixture of stable and nonstable form)
HA / Heat
from alcohol to alkene

favored in high temp

most commonly used acds are bronsted lowery acid proton donor

tert alcohol> second alcohol> primary alcohol

tert most reactive
used to identify which functional group sare present in a molcule

ony tell what type of bonds are present. NOT HOW MANY
IR spectroscopy
in IR spectroscopy, methanol and ethanol are distinguishable or indistinguishable
indistinguishable
1750 cm-1
carbonyl C=O
alcohol
braod 3000 cm-1 (approx)
carbonyl C=O
1750 cm-1
braod 3000 cm-1 (approx)
alcohol
sharp 3000 cm-1
amine N-H
amine N-H
sharp 3000 cm-1
peak at 2800-3500
acid, alcohol broad peak above 3000

amine sharp peak above 3000

alkane sharp peak below 3000
peak at 1750
carbonyl peak
-ketone
aldehyde
caroxylic acid
acid anhydrides
acid halides
aides
ester
carbonyl peak
-ketone
aldehyde
caroxylic acid
acid anhydrides
acid halides
aides
ester
peak at 1750
NMR stands for?
nuclear magnetic resonance
determine exact molecular structure
NMR
methane and benzene produce how many NMR signal?
one
how many sinal chorobenzene produce?
three

size of the signal corresponds to the number of the H.
chlorocyclohexane produce how many signal?
7 signal
you will see fuzzy blob instead of seven distinct peak
deshielding
downfield
bing inproximity to e- withdrawing functional group
inc value of sigma
means left on a NMR
SP3 carbon shows up in the what side of NMR
right
SP2 carbon shows up in the which side of NMR
left
SP2 carbon (C=C or C=O)
carboxylic acid in NMR
10-12 (left side of NMR)
aromatic H is in NMR
around 6-7
use light of shorter wavelength higher frequency and higher energy than IR
UV visable spectrosocpy
use to examine conjugated system
UV visable spectrosocpy
detect mass/mass ratio
molecular ion peaks quivalent to te molecular weight of the molecule
mass spectroscopy
benzene to benzene-X

halogenation
X2/FeX2
X2/FeX2
bezene to benzne-X

halogenation
benzene to benzene-NO2

nitration
HNO3 (conc) /H2SO4 (conc)
HNO3 (conc) /H2SO4 (conc)
benzene to benzene-NO2

nitration
benzene to benzene-SO3H

sulfonation
H2SO4 (fuming)
H2SO4 (fuming)
benzene to benzene-SO3H

sulfonation
benzene to benzene-R

friedel crafts alkylation
RX/AlCl3
RX/AlCl3
benzene to benzene-R

friedel crafts alkylation
benzene to benzene-C=O-R

friedel crafts acylation
RCOCl/AlCl3
RCOCl/AlCl3
benzene to benzene-C=O-R

friedel crafts acylation
-NR2
-OH
-OR
-R
Ring Activator(more reactive)
e- donating group


Para and orto
but chose para over ortho
Ring Activator(more reactive)
e-donating group


Para and orto
but chose para over ortho
-NR2
-OH
-OR
-R
ring deactivator(less reactive)

ortho and para director
-X (halogens)
i.e Bl, Cl
-X (halogens)
i.e Bl, Cl
ring deactivator(less reactive)

ortho and para director
more e donating(activator) is
basic
more e withdrawing (deactivator) is
acidic
ring deactivator(less reactive)

meta director
-NR3+
-NO2
-CN
-SO3H
-COR, CO2R
-NR3+
-NO2
-CN
-SO3H
-COR, CO2R
ring deactivator(less reactive)

meta director
PCC
alcohol to aldehyde(or to ketone if alcholis 2endary)
tollen's reagent
aldehyde to carboxylic acid
KMnO4
alcohol to carboxylic acid
K2Cr2O7
alcohol to carboxylic acid
alcohol to aldehyde
PCC
aldehyde to carboxylic acid
tollen's reagent
alcohol to carboxylic acid
KMnO4
alcohol to carboxylic acid
K2Cr2O7
primary alcohol when oxidize become
aldehyde and carboxylic acid
depending on the agent
secondary alcohol when oxidize become
ketone
tertiary alcohol oxidize?
do not oxidize
1. KMnO4, OH-
2. H+
alkene to 2 carboxylic acid
1. O3, CH2Cl2
2. Zn/H2O
alkene to 2 aldehyde
alkene to 2 carboxylic acid
1. KMnO4, OH-
2. H+
alkene to 2 aldehyde
1. O3, CH2Cl2
2. Zn/H2O
terminal alkene CHC=CH2 to
carboxylic acid and CO2
1. KMnO4 OH- heat
2. H+
NaBH4
aldehyde and ketone to alcohol
LiAlH4 (LAH)
aldehyde, ketone, ester, carboxylic acid

to

alcohol
aldehyde and ketone to alcohol
NaBH4
LiAlH4 (LAH)
aldehyde, ketone, ester, carboxylic acid

to

alcohol
grignard rxn
RMgX
RMgX (grignard rxn)
aldehyde or ketnone to alcohol by adding R-
william ether synthesis
R-O- Na+ and R-x

to

R-O-R + X- + Na-
acyl halide formation
carboxylic acid + SOCl2

to

R-C=O-Cl
more acidity
more e- withdrawing group
more basic
more e-donating group
zaitsev's rule
alkyl halides to dehydrogenation, you often have yield containing more than one product

more substituted and less substituted alkene

more substituted is stable
alkyl halides to dehydrogenation, you often have yield containing more than one product

more substituted and less substituted alkene

more substituted is stable
zaitsev's rule
when elimination yield the less substituted alkene we sa that it fllowe the ?
hoffman rule
hoffman rule
when elimination yield the less substituted alkene
E2 bimolecular elmination follow wich rule
both zaitsev's rule and hoffman's rule
E1 unimolecular emlimination follow
only saitsev's rule
cold dilute KMnO4
alkene to alcohol
O3, CH2Cl2/NaBH4, CH3OH
alkene to alcohol
creation of long high molecular weight chains composed of repeating subunit
polymerization
polymerization occur thru
radical mechanism
O3, CCl4/ H20
alkyne to carboxylic acid
naphthalene
2 benzene connected together
anthracene
3 benezene connected together
pyridine
benzene with N instead of one carbon
pyrrole
cyclopentane with N instead of one Carbon
anisole
benzene-OCH3
aniline
benzene-NH2
tolune
benzene-CH3
phenol
benzene-OH
CrO3
CrO3
CrO3
CrO3
CrO3 (jones reagent)
alcohol to carboxyolic acid

if secondary alcohol then to ketone
tollens' reagent
Ag2O
Wolff kishner (H2NNH2)
both aldehydes and ketones can be fully reduced to alkanes
clemmensem Hg(zn)/HCl
both aldehydes and ketones can be fully reduced to alkanes
both aldehydes and ketones can be fully reduced to alkanes
clemmensem Hg(zn)/HCl

Wolff kishner (H2NNH2)
Wolff kishner
(H2NNH2)
(H2NNH2)
Wolff kishner
clemmensem Hg(zn)/HCl
Hg(zn)/HCl
Hg(zn)/HCl
clemmensem
carboxylic acid to acyl halides
SOCl2/H+
carboxylic acid to amides
NH3