Study your flashcards anywhere!

Download the official Cram app for free >

  • Shuffle
    Toggle On
    Toggle Off
  • Alphabetize
    Toggle On
    Toggle Off
  • Front First
    Toggle On
    Toggle Off
  • Both Sides
    Toggle On
    Toggle Off
  • Read
    Toggle On
    Toggle Off
Reading...
Front

How to study your flashcards.

Right/Left arrow keys: Navigate between flashcards.right arrow keyleft arrow key

Up/Down arrow keys: Flip the card between the front and back.down keyup key

H key: Show hint (3rd side).h key

A key: Read text to speech.a key

image

Play button

image

Play button

image

Progress

1/122

Click to flip

122 Cards in this Set

  • Front
  • Back
HBr
What Reagent?
In a Williamson ether synthesis
1)what kind of molecule is made in the first step?
2)How is it made?
1) Alkoxide
2) Adding an alcohol to Na, K, or NaH
In a Williamson Ether Synthesis, what occurs if a secondary halide or tosylate is used?
Creates a possibility for an E2 Reaction to occur, which competes with the desired SN2, reaction usually sucks.
What does MCPBA do as a reagent?
Breaks an Alkene into an epoxide.
1)What kind of substance is MCPBA and CH3COOOH?
2)What do they do as reagents?
1)Peracids
2)Break alkenes into epoxides
What does CH3COOOH do as a reagent?
Breaks an Alkene into an epoxide
What Product?
.
HI
What Reagent?
What Reagent?
.
What Product?
.
What Product?
.
What hybridization are all carbons in a benzene ring?
sp2
1)What bond angle are all carbons in a benzene ring?
2)What shape does the ring take because of this?
1)120
2)Flat
What is the molecular mass of benzene?
78
Is a double bond or single bond longer?
Single
What bonds are longer in a benzene ring?
All benzene bonds stretch to the same size
What happens in an aromatic to allow resonance stabilization?
P-orbitals line up parallel to allow electrons to move freely from one to the other
What is the kekule structure?
What does it symbolize?
Constant resonance
How stable is benzene? How reactive?
Very Stable. Very unreactive.
Define Aromaticity
High Stability, usually due to resonance stabalization
How do you determine if a molecule is aromatic?
1)Cyclic
2)Planar compound - must have all atoms in ring in sp2 hybridization
3)Must have Huckel # of pi electrons
What is the Huckel Rule?
In order to be aromatic the ring must have 4n+2 pi electrons where n=0,1,2...
What are the first four Huckel Numbers?
2,6,10,14...
How do you know if a compound is anti-aromatic?
Must be cyclic and planar, but no huckel number of pi electrons exists. Has 4n Pi electrons
What is a heteroatom?
N, O, P, S..
What does the atomic number signify in a neutral atom
The number of protons in the nucleus and the number of electrons surrounding it
What does the mass number signify in a neutral atom
Sum of the number of protons and neutrons in nucleus
What does the Heisenberg Uncertainty Principle state?
The exact location of an electron can never be determined, but the orbital defines where there is a high probability of finding an electron with a certain energy.
Explain the arrangement of electron density of a 2s orbital.
Has a small region of high electron density close to the nucleus, but most of the electron density is farther from the nucleus, beyond a node, or region of zero electron density.
What is the Pauli Exclusion Principle?
There are a maximum of 2 electrons in each orbital (spins must be paired)
What is the Aufbau Principle?
Electrons "build up" the orbitals from lowest energy to highest energy.
What is Hund's Rule?
Electrons "build up" or "fill" one orbital at a time in a sublevel and then pair.
How is the major contributor of a molecule with resonsance determined?
1) As many octets as possible
2) As many bonds as possible
3) Any negative charges on the more electronegative atoms
4) As little charge seperation as possible
Arrhenius Acid
substance that ionizes/dissociates in water to give a hydronium ion
Arrhenius base
substance that dissociates in water to give a hydroxide ion
How is pH calculated?
pH = -log[H3O+)
Bronsted-Lowry Acid
any species that can donate a proton
Bronsted-Lowry Base
any species that can accept a proton
Lewis base
an electron pair donor, nucleophile
Lewis acid
an electron pair acceptor, electrophile
degenerate orbitals
orbitals with identical energies
conjugate acid
acid that results from the protonation of a base
conjugate base
base that results from the deprotonation of an acid
constitutional isomers
isomers that are connected differently, differing in bonding sequence
structural isomers
isomers that are connected differently, differing in bonding sequence
stereoisomers
isomers that differ only in how their atoms are arranged in space
cis/trans isomers
stereoisomers that differ in their cis-trans arrangement on a ring or a double bond
geometric isomers
stereoisomers that differ in their cis-trans arrangement on a ring or a double bond
axial bond
one of six bonds (three up and three down) on the chair conformation of the cyclohexane ring that are parallel to the "axis" of the ring
The most stable conformation of cyclohexane
Chair conformation
cracking
heating large alkanes to cleave them into smaller molecules
equatorial bond
one of the six bonds (three down and three up) on the cyclohexane ring that are directed out toward the "equator" of the ring.
spirocyclic conformation
bicyclic compounds in which the two rings share only one carbon atom
The first propagation step is ____ for bromination but ____ for chlorination.
endothermic, exothermic
The transition states forming the primary and secondary radicals for the ____ ____ have a larger energy difference than those for the ____ ____.
endothermic bromination
exothermic chlorination
In a ____ reaction, the transition state is closer to the products in energy and in structure.
endothermic
In a ____ reaction, the transition state is closer to the reactants in energy and in structure.
exothermic
Hammond postulate
Related species that are closer in energy are also closer in structure. The structure of a transition state resembles the structure of the closest stable species.
Name of a benzene with an -OH
Phenol
Name of a benzene with an -NH2
Aniline
Name of a benzene with a -CH3
Toluene
Name of a benzene with an -OCH3
Anisole
Name of a benzene with a -COOH
Benzoic Acid
Name of a benzene with a -COH
Benzaldehyde
What kind of substituent configuration does ortho represent?
1,2
What kind of substituent configuration does meta represent?
1,3
What kind of substituent configuration does para represent?
1,4
What does a benzene ring require to proceed in a substitution reaction?
Super strong electrophile
What does the halogenation of a benzene require?
Lewis acid catalyst
What catalyst is required for the chlorination of a benzene?
FeCl3 or AlCl3
What catalyst is required for the brominatino of a benzene?
FeBr3
How would you brominate benzene? How would you chlorinate?
Br2, FeBr3
Cl2, FeCl3 or AlCl3
What hybridization does the reactive carbon have in its intermediate state of an electrophilic aromatic substitution reaction?
sp3
What hybridization does an aromatic carbon have? What hybridization is the end product of the carbon after electrophilic aromatic substitution?
sp2, sp2
How do you iodinate an aromatic?
I2, HNO3
What reagents are required for the nitration of an aromatic?
HNO3, H2SO4
How does HNO3 and H2SO4 act as reagents to nitrate an aromatic?
H2SO4 is a much stronger acid so it donates a proton to the less stronger acid, HNO3. The HNO3 acts as a base and accepts the proton. H2NO3 loses water and NO2 is formed, which reacts in the substitution.
What can be used to reduce nitrobenzene to aniline?
Zn, Sn.. , HCl
How is an aromatic sulfonated?
SO3, conc. H2SO4
An electron withdrawing substituent on an aromatic ring is:
activating/deactivating
ortho/meta/para director
deactivating
meta director
An electron donating substituent on an aromatic ring is:
activating/deactivating
ortho/meta/para director
activating
ortho/para director
A halogen on an aromatic ring is:
activating/deactivating
ortho/meta/para director
deactivating
ortho/para director
2,4-dimethylpentanol
Structure?
Name?
cyclohex-3-en-1-ol
Structure?
Name?
6-bromo-5-methyl-2,3-hexandiol
Structure?
Name?
It is a general principle that reactions proceed towards ___ reactive species.
Less
What is the stability of the following starting with the most stable to least stable?

CH3CH2O-
ClCH2CH2O-
CH3O
Cl3CCH2O-
Cl3CCH2O-
ClCH2CH2O-
CH3O-
CH3CH2O-
What is the reactivity of the following starting with the most reactive to least reactive?

CH3CH2O-
ClCH2CH2O-
CH3O
Cl3CCH2O-
CH3CH2O-
CH3O-
ClCH2CH2O-
Cl3CCH2O-
3 > 1 > 2
Number from most to least stable
What product?
.
Product?
.
What reagent(s)?
.
What starting material?
.
What product?
.
What reagents?
.
What starting material?
.
What product is formed when combining a grignard reagent and an aldehyde?
Secondary alcohol
What product is formed when combining a grignard reagent and a ketone?
Tertiary alcohol
What product is formed when combining a grignard reagent and formaldehyde?
Primary alcohol
What product?
.
What reagents?
.
What starting material?
.
What product?
.
What product?
.
In order to get a tertiary alcohol from a grignard reagent and an acid chloride, what must occur?
Grignard reagent must react twice with the acid chloride.
In order to get a tertiary alcohol from a grignard reagent and an ester, what must occur?
Grignard reagent must react twice with the ester.
What kind of product(s) are formed when a grignard reagent is reacted with an ester?
A tertiary alcohol and a primary alcohol
What product?
.
What reagents?
.
What starting material?
.
What product?
.
What reagents?
.
What starting material?
.
Synthesize with:

a)grignard reagent and a carbonyl.
b)organolithium and a carbonyl
c)grignard reagent and acid chloride
.
Synthesize.
.
Synthesize with:
a)Grignard reagent (2 ways)
b)Organolithium
.
1)Grignard chemistry will not work with a molecule with these functional group(s).
2)This will happen instead of the grignard reaction
3)This happens because
1) Hydroxyl, sulfhydryl, -NH
2) Acid/Base reaction. The Reactive group from the grignard reagent will remove the H from the acidic O, S, or N, and the acidic atom that lost the proton will bond with the organometallic.
3)It takes less energy
Define Oxidation
Addition of O content or removal of H
Define Reduction
Addition of H content or removal of O
When a molecule is in its most oxidized state it is ____ to reduce.
difficult
If you wanted to reduce a ketone or aldehyde what could you use?
LAH or NaBH4
If you wanted to reduce a carboxylic acid what could you use?
LAH