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exam 2
definitions
32
Organic Chemistry
Undergraduate 2
11/20/2012

Additional Organic Chemistry Flashcards

 


 

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Term
a reaction in which two species combine to make a third
Definition
addition reaction
Term
a reaction in which the reactant seperates to form two products
Definition
elimination reaction
Term
a reaction in which two reactants exchange substituents in order to form two different products
Definition
substitution reaction
Term
a reaction in which an isomer is formed
Definition
rearrangement reaction
Term

a reaction where each neutral reactant supplies an equal part of the bond (one electron)

vs. 

a reaction in which one reactant supplies an electron pair

Definition

homolytic reaction

vs. 

heterolytic reaction

Term
what is another word for an asymmetrical/heterolytic reaction?
Definition
polar reaction
Term
what are the three steps of radical reactions?
Definition

1. initiation

2. propagation

3. termination

Term
polarizable atom
Definition

an atom that can be influenced by its environment (have its electron field manipulated) and therefore can become more polar

- LARGER atoms are more polarizable

 

Term
a reaction in which an electrophilic species bonds with a nucleophilic one
Definition
electrophilic addition reaction
Term
what you get if you divide the products of a reaction by the reactants
Definition
the equilibrium constant
Term

which reaction will be faster:

 

K = 1.5

K = 0.5

Definition
it's impossible to say! Activation energy determines rate of reaction, NOT the equilibrium constant
Term
enthalpy
Definition
ΔH; how much heat is stored in the bond
Term
equation for Gibbs free energy
Definition
ΔG° = -RTlnK = ΔH° - TΔS
Term
bond dissociation energy
Definition
how much energy is stored in a bond - i.e. the enthalpic change when a bond is broken or formed
Term
methylene, vinylic, allylic
Definition

methylene: H2C=

 

vinylic: H2C=C-H

               |

 

allylic:

 

H2C=C-CH-CH2-

Term
What happens to stability of an alkene as they become more highly substituted and why?
Definition

More highly substituted alkenes are more stable.

 

1. hyperconjugation (stabilizing interactions between the pi bond and neighboring C-C sigma bond

 

2. sp3-sp2 are more stable than sp3=sp3

Term
Markovnikov's rule
Definition

- the rich get richer

- regiospecificity

Term
when specific parts of a reactants end up on certain places in the product
Definition
regiospecificity
Term
why are carbocations more stable when highly substituted?
Definition

- hyperconjugation (stabilization of empty p orbital and nearby, properly oriented sigma bonds)

 

- inductive effect (alkyl groups are larger; therefore more polarizable; therefore their charge shifts to the carbocation and stabilizes it)

Term
How do you explain the fact that a more stable carbocation intermediate means that the activation energy is lower and the reaction happens faster?
Definition

Hammond Postulate: the transition state will physically resemble the species closest to it in energy. 

--> reaction to become a carbocation is endothermic, therefore the TS resembles the carbocation intermediate, therefore it is more stable, therefore it takes less energy to form, therefore it forms faster

Term
in a magnetic field (B0), number of possible electron spin states
Definition
2I+1
Term
when the nuclei have been irradiated so that they are all spinning in the antiparallel, high energy state
Definition
resonance
Term
B0
Definition
strength of the external applied magnetic field applied to flip parallel electrons antiparallel (resonant)
Term
Rf
Definition
radio frequency - the energy required to bring 1into resonance
Term
what is the difference between Band Rf?
Definition

first one: is the energy applied to get all the electrons spinning either antiparallel or parallel

 

second one: energy needed to get the parallel spinning ones to spin antiparallel instead (resonate)

Term
chemical shift
Definition
location of a nuclear signal on the x-axis based on electron shielding
Term
NMR standard species
Definition
TMS (tetramethyl silane)
Term
DEPT
Definition

1. broadband decoupled shows ALL carbon shifts

 

2. DEPT-90 shows ONLY CH

 

3. DEPT-135 shows CH and CHabove and CH2 below the x-axis

Term
if replaced with X, the molecule would be identical to others
Definition
homotopic
Term
replacement of a proton would create a chiral center
Definition
enantiotopic
Term
replacement with a proton would create a SECOND chiral center
Definition
diastereotopic
Term
coupling constant (J)
Definition
the distance between coupling peaks; two groups coupled to each other will have the same J
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