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Organic chemistry exam reviews
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, Chapter 4 ↑T-
Cycloalkanes
have the formula Cutten If they have
Ey
a Cycloallaves
will be
gene one
rig treated
as
If the
ring is smaller than what its attached to ,
It will be treated as a substituent Subst , trut
6) make substituents the 2nd substituent has the lowestnumber possible
If 2
sure when
counting
or more substituents have the same number ,
use alphabeth order
e) Cis and trans isomerism in alkares D
↳If both substituents have both
#I
wedges/dashes , than theywe cis
Trans-CIS-
If one
↳
substituent and the other dashed then it is trans
is wedged is ,
↳ Cis and trans interconvented
lowers are stable combounds and can't be
d) Ring Strains
-
angle strain :
happens when bond angle are distorted from the normal
shys
Torsional strain When theres eclipsing (atoms are coreng atoms)
-
:
-
Steric Whe atoms are too close
-
forced to occupy the same space
logether ,
E) Chair Conformations
Chair conformation
-
is the most Stable Conformation , boat conformation is the least stable
axial and equatorial CH3 aXia up
Bu e =
axial up and down 16 ring)
--
x
is in
&-
-
uxal down
equatorial side-to-side (6 rung) y
-
is in
↳ each
haben has one equatored and one axial equiour
the more the
equatorial bands , the more stable the Conformation is. the less strain ,
-
loss
↳ doe mugs
to 1
3-diaxial interactions
, .
The trans only exists in diequiturial conformations
-
isormer
Ring flips
to do a ring flip , redraw the chair the opposite way and renumb or
-
↳ the
equituria down turns into axial down , the axial up turns inso epultorid up etc .
CH3 Br
up93
Ft
& us vs trans
/ i
.
//
- chiz down
air
Ths i Br/Fa/VBr
-
y
Cis must always have l axial and
Lepuitorial
trans must have either both axial or
both equltorad
, Chapter 5 Stereochemistry
:
at tetrahedrel centers
1) handednes :
enastomers images of a compound
are mirror
are bonded to a carbon I diff
↳ when
I diff
groups ,
arrangents are possible (enantomess)
Chirality Molecules that not superimposable
·
:
their mirror
are on
image
↳
Chirality Centers is a carbon connected to 4 different
groups
-
Chiral Molecules do not have
plane at Moloculos that do are achival
a
symmetry ,
4
CHz -CH3 ,
C= 0
,
C= C
,
and CEC Carnet be Chirality centers
,
Optical actiety
Chiral Molecules rotate the plane ot plane-polarized which means chiral molecules
light
-
,
are optically active . Achival Molecules are optically Inductive
a compound whose solution rotates PPL to the
right dextratory
[t a
is
-
compound whose solution rotates PPL to the left is leveratory
Stericisomers and configurations
rules for
assigny configurations at chirality center
·
a
as rank each atom by Atomic number
(bigger Atomi number-higher Priority
b) if it is the same atom look at the second and third atoms
when
company ,
C) double and triple bonded atoms the A of bonded atoms
same as the
single
are
d) Rotate the molecule so that the lowest dash (usually Hydrogen)
priority atom is on a
5)
If Clockwise His R
Priority goes goes counterclockwise
the if it ,
It is S
.
,
·
optical rotation is not related to S & R
. Meso compounds
Br Br Br
B
i) diasteromers ↓i
↳ stereolsomers that are not Mirror images
a
roll12-2110H
i i
-can only
change one or two from dash to
Wedge ........ a dastreme
Epimens diasteremes that only differs at chirality center
-
Br
the the DCH Bu
... achral =
oc-cot
I
ii) meso compounds
a
i i
↳ has
chirality Centers but has a plane of symmetry
,
↳meso
compounds are activel
Physical Properties of compornes diastercomers and racemic mixtures differ from eachother and from the Properties
-
mess ,
of enauctions
iii) racemit mixtures
↳ a racemic mixture
(vacemates is a so:so mixture of two eventiomers
-
have O optical rotation
, If avacemic mixthere of a carboxylic acid reacts with a chival amine the Product
ammonium salts the diastumes Racemic
N) Prochirality
I
" ↑
↳ a molecule is prochiral if it can be converted 3/112 -
2
+ - 2113
O
from achival to chird in chemical step 4
a
single 4
·
Re is Clockwise So %
50 %
·
Si is counter clockwise
reactions
Chapter G :
Organic
1) Types of
organic reactions
-
addition : when two compounds make one product
elimination : When a single reactant Splits into
2 products
Substituti when two reactants
exchange Parts to yelld two new products
-
:
When a
single product undergoes a rearranget bonds yel two
of to
-rearrangement :
new products
② When from decrease of # of bonds It Is addition bonds eliminatio
you go a ,
increase in is
Reaction mechanisms
" describes the bonds Broken and formed in a chemical reaction , and accounts for all reactants
and Products
·
Bond
Breaky and formation in chenne reactions
-
symmetmel Bond Browly is homolytic (If one electron remains with each fragment
unsymmetrical Bond Breaking is heterolytic (If both electrons stay with one fragment
-
whee the other has none
(11) Polar reactions
↳ happens because diff
bond Polarities within molecules Usually bes
ot in -
ofMectronegatily diff between atoms
-
In Polar reactions electron rich sites interact with election poor
Sites .
-the movenut of elections is shown by a curve arrow
IV) reacting species
af a nucleophile is a compound with an election rich atom
b) compound with an election poor atom
an electrophile is a
as some compounds can behave as both nuclophiles↑ electrophils
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