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Organic chemistry Exam 2
Organic chemisistry Capter 5-6
69
Organic Chemistry
Undergraduate 2
03/08/2011

Additional Organic Chemistry Flashcards

 


 

Cards

Term
rules for polar reactions
Definition
1. e- move from e- rich --> e0 poor environments
2. nucleophiles e- rich rxn (either neutral or negatively qed (Nu:) lone pairs or neg anions (Nu-)
3. electrophiles are neutral and pos. cations E or E +
4. DO NOT BREAK THE OCTET RULE or valence shell has a LIMIT for electrons --> octet rule for 2nd row ( ONLY 4 BONDS PER CARBON)
Term
hierarchy for reaction
Definition
1. lp--> bond
2. Bond--> LP
3. Bond-->bond
4. LP--> LP
Term
nucleophile define
Definition
electroneg atom that wishes to give electrons to + atom (electrophile)
Term
how do you determine which atom is more stable to cary a neg. charge

-CIH2 or I-
Definition
I- is going to be produced because electroneg atom or large atom is going to hold a - q and be more stable because of large space for - to move around
Term
what do arrows represent in a mechanism
Definition
flow electrons no direction of atom
Term
what is true about a system that goes completely in to products
Definition
delta G = - --> favored reaction --> exergonic

G= products- reactant

reactants have higher power then products
Term
delta G,

define
-sign for favored(spontaneous)
-sight for unfavored
- how to calculate off of E chart
Definition
delta G- free E of system
- (-) G favored spontaneous--> all products ---> exergonic
(+) G unfavored no reaction -enderonic
- products- reactants
Term
exergonic
Definition
- G , favored reaction, E lost by chemical system and released to surrounding
Term
endergonic define
Definition
unfavored +G reaction , E is absorbed by the chemical system from the surrounding
Term
delta H
Definition
heat of reaction- the measure of the change in total bonding E during a reaction
Term
define exothermic
Definition
H- : bonds in products are stronger more stable than the bonds in the reactants, heat is released and the retain is exothermic
Term
Endothermic
Definition
H+, bonds in the products are weaker les stable, than the bonds in the reactions, heat is absorbed, and the reactions endo thermic
Term
remember the more E a system of molecule has the MORE UNSTABLE it is
Definition
Term
delta S represents what?
Definition
measure of the change in the amount of RANDOMNESS that accompanies a reaction
Term
a --> B+ C ; ENtropy is changing how
Definition
increasing, more molecules more randomness due to clamming
Term
s- represents
Definition
ransoming decreasing

A + B --> C
Term
S + represents
Definition
randomness increasing
Term
Transition state controls what??
Definition
THE RATE OF REACTION
Term
G double dagger defines what??

how do you find it in a graph??
Definition
defines the RATE OF REACTION -->through the Ea

Peak - the previous base connected to wave
Term
which one controls the rate of a reaction???


DDG1 or DDG2???
Definition
DDG1 because it has a higher E, must go through the TS1
Term
ENDERGONIC REACTION
Definition
REACTANTS HAVE LOWER E THAN PRODUCTS (WHICH HAS HIGHER)
Term
DDG REPRESENTS
Definition
THE E DIFFERENCE OF THE TRANSITION STATE
Term
WERE CAN INTERMEDIATES BE FOUND
Definition
DIP WITHIN A PEAK
Term
KNOW HOW TO DRAW GRAPH IDENTIFY EACH COMPONENT
KNOW WHAT EACH REPRESENTS
DIFFERENCE B/W EERGONIC/ENDERONGIC
FAVORED UNFAVORED
ACTIVATION E
WHAT CONTROLLS THE RATE OF RXN
Definition
Term
WHAT IS THE BOND DISSOCIATION E,

WHAT IS IT RELATED TO
Definition
AMOUNT OF E IN GAS OHASE TO HOMOLYTICALLY BREAK A BOND,
AND HOW MUCH E YOU GET OUT OF IT TO MAKE NEW BONSD
Term
EXOTHERMIC GRAPH
Definition
PRODUCTS HAVE LOWER E THEN REACTANT
Term
HOW DO YOU DETERMINE THE RATE OF REACTION
Definition
BASED OF DDG--> THE SMALLER THE NUMBER THE FASTER THE RECTION
Term
ENDOTHERMIC REACTION
Definition
PRODUCTS HAVE HIGHER E THEN REACTANT
Term
HAVE DOES CATALYT EFFECT REACTION
Definition
CHANGE THE MECHANISM OF REACTION--> LOWERING THE DDG--> CAUSING OVERALL DECREASE IN REACTION
Term
for nomenclature of alkenes include the double bond as -nee

when numbering make suers double bond gets the LOWESt number int he longest chain

make sure to identify where the double bond is located

2-decene or dec-2-ene
Definition
Term
degrees of unsaturation
3 rules for unsaturation
Definition

1 * # rings 1* # double bonds 2* #triple bonds *** make sure you don't screw this up tips: circle all components c14H19N 1. halogens = hydrogens add to total 2. oxygen is IgnOred 3. N must subtract 1 from the original alkane vs ene or yene

 

  1. Halogen = hydrogen
  2. IgnOre - oxygen
  3. Nitrogen --> Neg--> subtract 1h
Term
what is the function of E Z system
Definition
to identify atom locations priority on a double bond
Term
define Z/E RULES
Definition
the key to E is ATOMIC NUMBER

Z- HAS HIGHER PRIORITY GROUPS ON THE SAME SIDE
(Z AS IN PARALLEL FROM EACH OTHER)

E- OPPOSITE
(E IN OPPOSITE)
Term
RULES FOR E/Z SEQUENCE
Definition
1. CUT THE DOUBLE BOND IN HALF, DETERMINE ON EACH SIDE WHICH OF THE 2 ATOMS HAVE HIGER PRIORTY
2. IF THE FIRST ATOMS ARE ON EACH BOND ARE THE SAME, LOOK AT THE ATOM CONNECTED TO THAT ONE

- tip: write out all atoms connected to that atom

3. groups, if there is no difference in priority between the first atoms connected to the chiral center (they are both carbon), then you look at the next atoms in the group. One has 3 H atoms and the other has two H atoms and one oxygen atom. The oxygen is higher.
Term

http://www.khanacademy.org/video/naming-alkenes-examples?playlist=Organic%20Chemistry

 

naming clyclo enes**

Definition
  1. when solving cyclos first point of double bond is usually assumed to be one (no identification needed)
  2. if there is a subst directly bonded to double bond then THAT is one
  3. must move across double bond like a bridge no matter what
Term
the higher the carbon bonding, the stinger lower the energy the molecule

Head of hydration will be lower --> more stable

greater c bonding
Definition
Term
saturated
Definition
A molecule with only single bonds is said to be "saturated.
Term
unsaturated
Definition
presence of multiple bonds introduces what is known as "unsaturation"
Term
how to calculate total degree of unsaturation
Definition

(# of double bonds) + (2 x # of triple bonds) + (# of rings)

 


Note that a triple bond counts for two degrees of unsaturation, because a triple bond contains two pi bonds.

Term
formula for degree of unsaturation given chemical formula
Definition

 

Degree of Unsaturation =
[2 + (2 x #Carbons) + #Nitrogens - #Hydrogens - #Halogens]/2

Term
what is considered saturated and what is not?
Definition

**unsaturated: rings, double bonds, tripple

saturated- none of the above

Term
my way of solving for unsaturation
Definition
  1. take formula given
  2. subtract 2 (getting all inside carbons) multiple by 2
  3. add 6
  4. subtract formula found by given
  5. divide by 2 = unsaturation

**don't forget to: 1. sub 1H = 1N

2. ignore O

3. 1hal = +1 H

Term
define markovnikov's rule
Definition

states that the more stable product

 

1. more hydrogens will want more hydrogens

 

or

 

 

2. more groups will want more groups

 

note: b/c carbocation bonded to more carbons will be more stable because it is able to share some of the electron clouds to keep it stable

 

more stable 4>3>2>1 least stable

 

Term
Markoknikov's rule
Definition

halide always ends up on more substituted carbon

 

least stable 1<2<3<4 most stable

Term

why is cl attach to more substituded carbon in terms of E

 

Definition
delta H in energy char should be lower
Term
hyperconjugation function in carbocations
Definition

stabalizing effect- non bonded resonance

e- are pushing against eachothers e- orbitals --?

 

hyperconjugation is the interaction of the electrons in a sigma bond (usually C–H or C–C) with an adjacent empty (or partially filled) non-bonding p-orbital or antibonding π orbital or filled π orbital, to give an extended molecular orbital that increases the stability of the system

Term

most electroneg atom resides on more substitudteded carbon

 

markovnikov

Definition
Term
hammond postulate
Definition

is a hypothesis, derived from transition state theory, concerning the transition state of organic chemical reactions, which states that:[1]

If two states, for example, a transition state and an unstable intermediate, occur consecutively during a reaction process and have nearly the same energy content, their interconversion will involve only a small reorganization of the molecular structures.

ammond's postulate is useful for understanding the relationship between the rate of a reaction and the stability of the products.
- While the rate of a reaction depends just on the activation energy, the final ratios of products in chemical equilibrium depends only on the **standard free-energy change ΔG (“delta G”). The ratio of the final products at equilibrium corresponds directly with the stability of those products.

** most stable product is not always the one that is favored in a reaction process.


then what is??



Term
why is most stable product not always the one that is favored in a reaction process, what could be the reason?
Definition
Term
funciton OH- in reaction
Definition
strips H to produce H2O
Term
product of dehydartion
Definition
OH + H --> H2O
Term
in dehydration reaction THF or ether with H3O/H2SOF can be used for dehydration
Definition
Term
regiochemistry
Definition
where the reaction takes place, in what region of the molecule is reaction taking place. location of double bonds
Term

anti-markovnikov

 

 

Definition
where electroneg atom or halide does not occur on more substituded carbon
Term
what if you see peroixe (RooR) with H-BR means what to the reaction
Definition

ROOR peroxide will produce a radical

 

(ROH) ( BR. radical) which will attack to double bonds producing more stable carbon cation intermediate

 

radical causes ANTI-MARKOVNIKOV addition

Term
h2o2
Definition
antimark reaction
Term
ether
Definition
markovnikov reaction
Term
chapter 5
Definition
Term
homolytic cleavage
Definition
unsymmetrical cleavage
Term
heterolytic cleavage
Definition
unsymmetrical cleavage
Term
radical reaction (free radica)
Definition
process that involve symmetrical bond0breaking and making
Term
polar reactions
Definition
processes of unsymmetrical bond breaking and making
Term

radical reaction

3 steps

Definition
  1. initiation
  2. propagation
  3. termination
Term
initiation
Definition

irradiation with light

reactions beings by breaking relatively weak cl-cl bonds using light

Term
propagation
Definition

reactive radical cholorine collides with methane molecule ina  propagation step chain reaction

cl. + HCH3 --> HCL CH3.

Term
termination
Definition

2 radicals colliding and combine to form stable product

 

Cl. + Cl. --> Cl-Cl

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