this Organic Chemistry II exam review covers key topics like reaction mechanisms involving carbonyl compounds, aromatic substitution, and the chemistry of carboxylic acids and their derivatives. It includes multi-step synthesis strategies, advanced spectroscopy (NMR, IR), and the reactivity of conj...
Chapter 14 conjugated compounds : and UV spectroscopy
Conjugated compounds
↳ compounds with
alternating double and single bonds
↳
They by using base induced elimination of
are made HX from an Allylichalide
↳ The middle
single bond in a conjugated diene is shorter
HA Br
NBs KockHala
than a non conjugated one ↑
due to orbital hybridizati 4 HOC((Hzbe
Cyclohexene S-Bremocyclohexene 1,
3-Cyclohexadiene (76 %)
·
substituted alkenes are more Produce less heat
stable and
So they release heat when added to water
one diff btwn cony dienes and alkenes
.
is electrophilic addition rxns
1,2 & 1
,
4 addition
Sometimes conj. dienes can get 2 products and ,
one will have the alkene on the central
Carbon 1 2 1, 4
,
HBr
Nisr
-
x +
1 ,
3-butadiene It i
1 ,
2
1 4
Br 2
,
- -Br
20 %
Br
t
B Bo
d Inajor Minor
12
129134
#
2
1 ,
"
+
it [a
c Kinetic
T
therm
namic
1, 2 1 4
Kinetic and themodynamic control
,
Kinetic control : The Product of an irreversible ran. depends on reletve ratos not stability
↳ Low Product with lower Ea will form greater amounts
temp ; Irreversible .
in
thermodyname control : Product is reversable depends on Stability ,
not relative rates
↳ high temp ; reversable
.
when we have an Irreversbe lower tempran ,
product will depend relate rates . If we have a
higher temp reversable rxy , major product will depend on stability
Diels-alder cycloaddition reaction
↳ cons-dienes
undergo an addition run with alkenes to make subst Cyclohexone products·
, dienophile
diene O
diels-alder rxn =
DAR
.
5 y or #
S
↳3 butadene 3-butene-2-ove 3- Cy clohexany
methyl ketone
↳
This process is called the diels- alder cycloaddition reaction
not polar or radical
dienophile : alkene Part of DAR
(dieve cover)
*
DAR can
happen quicker when the dienophile has an EW Substituent Group Stereospecific : a single
Product Stereoisomer is formed . e
ex
alkynes can
i
·
also act as dienophiles .
can as product , trans Product
b UV Spec
Predict the following diels -
alder rxn endo (Syn) .
-1 P electrons can be shifted
by Ultraviolet light
>
-
-
Y
When "white
- light strikes
-
a cony
Molecule
. The wavelength needed for
exitation is Absorbed
The dienophile
·
has to have an ewo and can sometimes have a triple bond
Stereochemistry of dienophile Maintained during the reaction
·
the is
The Diene
·
has to have (is-like") Conformation to do DAR .
to create
Some can rotate a S-cis Conformation
rigid ones can't
·
.
·
diens are very reactive and have an s-as geometry
Diene Polymers
·
like simple alkenes , con) · diones can polymerized
-
because double bonds remain in the Polymer as-trans isomerism is possible -
Polymerizati Can be initiated by radical add
-
or
Polymereati addition
-
Occurs via 1 4
,
HOMO highest electron filled orbital
!
:
Lumo : Lowest electron Poor orbital
Y2-Ys is hom
N4-Ns is Lumo
, 15 Benzene and aromaticity
Chapter
:
CHs
#
naming
Exis
aromatic compounds :
-
a lot of aromatic compounds have nonsystemic names
O-zylene
-more substituted benzenes are named the same way as other hydrocarbons ,
with benzene as the parent
tolvene Phenal anilive benzaldehyde
name
Exc KJXN
, G
alkyl Subst benzenes are named 2 ways :
alkyl-substituted Pheny
. in
If the alkyl substituent has 6
·
or less carbons its named as an
If the
alky) substituent has than 6 carbons Its named phenyl-substituted alkone
·
more , as a .
The Cotto CHy group denzyl group and the
Cals-group phenyl group
·
is a is a
disubstituted benzenes
↳ named
by the Ortho (0) meta (m) ,
and Para(p) system
,
O-dichlorobenzene
or tho met a Para P
-C3 #i
I . &
I Eis Br
**
Bir
M-Bromofoliere p-chloroBromobenzene
benzene with more than 2 substituents are named by numbering the position of each substituent
↳
Name like any other
namey
of benzene
Stability
addition products
benzene reacts Slowly with Bra give substitution
to not
-
,
↳ all
C-c bonds at benzene have the same length
-
benzene is Planar with all bond angles at 1200
&doe
& double bonds
-All carbons are sp2 hybridized and identical 4 it electrons
for to be arematic , i has to fulfill hickes rule
a
compound
hickes rule : a compound is only crematic If I has a plather , Monocycli system of Conjugati with a total of 4nt2
electrons
-
Molecules with (4 ,
8 , 12 ...
) are anticromatic
ex .
Cyclobutadiene (n 4) is =
anti
benzene (n c) aromatic =
Aromatic lons
·
any cyclic cony. Molecule with An + 2 electrons can be aromatic even ifIts an on
,
Voordelen van het kopen van samenvattingen bij Stuvia op een rij:
Verzekerd van kwaliteit door reviews
Stuvia-klanten hebben meer dan 700.000 samenvattingen beoordeeld. Zo weet je zeker dat je de beste documenten koopt!
Snel en makkelijk kopen
Je betaalt supersnel en eenmalig met iDeal, creditcard of Stuvia-tegoed voor de samenvatting. Zonder lidmaatschap.
Focus op de essentie
Samenvattingen worden geschreven voor en door anderen. Daarom zijn de samenvattingen altijd betrouwbaar en actueel. Zo kom je snel tot de kern!
Veelgestelde vragen
Wat krijg ik als ik dit document koop?
Je krijgt een PDF, die direct beschikbaar is na je aankoop. Het gekochte document is altijd, overal en oneindig toegankelijk via je profiel.
Tevredenheidsgarantie: hoe werkt dat?
Onze tevredenheidsgarantie zorgt ervoor dat je altijd een studiedocument vindt dat goed bij je past. Je vult een formulier in en onze klantenservice regelt de rest.
Van wie koop ik deze samenvatting?
Stuvia is een marktplaats, je koop dit document dus niet van ons, maar van verkoper malbedawe. Stuvia faciliteert de betaling aan de verkoper.
Zit ik meteen vast aan een abonnement?
Nee, je koopt alleen deze samenvatting voor €19,82. Je zit daarna nergens aan vast.
