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Organic chemistry exam reviews

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in depth review for all organic chemistry exams, simplified and easy to understand.

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  • August 11, 2024
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malbedawe
, 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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