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223 Cards in this Set
- Front
- Back
- 3rd side (hint)
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what are alkanes?
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aliphatic hyrdrocarbons (have only c-c and c-h sigma bonds)
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What are acyclic alkanes?
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alkanes with only linear and branched chains of carbon atoms.
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what are acyclic alkanes also called?
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saturated hydrocarbons -because they have the maximum number of of hydrogen atoms per carbon.
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what molecular formula do acyclic alkanes follow?
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Cn+ H2n+2
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What are cycloalkanes?
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alkanes that contain carbons joined in one of more rings.
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what is the molecular formula of cycloalkanes?
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CnH2n (have 2 fewer H atoms than an acyclic alkane with the same number of carbons)
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what are lewis structures not meant to imply?
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any three-dimensional arrangement.
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what is an isomer?
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two (or more) different compounds with the same molecular formula
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what are the two major classes of isomers?
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1. constitutional/structural isomers
2. stereoisomers |
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what is a constitutional/structural isomer?
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compounds with the same molecular formulas differ in the connectivity of their atoms.
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what are two types of acyclic alkanes?
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1. straight-chain alkanes
2. branched-chain alkanes |
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are branched-chain and straight-chain alkanes considered isomers?
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Yes, they are constitutional isomers. (ex: butane and isobutane)
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what is a primary carbon?
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a carbon bonded to one other carbon
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what is a secondary carbon?
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a carbon bonded to 2 other carbons
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what is a tertiary carbon?
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a carbon bonded to 3 other carbons
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what is a quarternary carbon?
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a carbon bonded to 4 other carbons
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what is a primary hydrogen?
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a hydrogen bonded to a carbon that is bonded to one other carbon.
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what is a secondary hydrogen?
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a hydrogen that is bonded to a carbon that is bonded to 2 other carbons.
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what is a tertiary hydrogen?
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a hydrogen that is bonded to a carbon that is bonded to 3 other carbons.
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what does n-alkane stand for?
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"normal" alkane (straight-chained)
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what is a CH2 group called?
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a methylene group
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what do you call a group of compounds that differ by only one CH2 (methylene) group?
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a homologous series
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what suffix to all alkanes end in?
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-ane
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what does the syllable preceding "-ane" identify when naming an acyclic alkane?
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the number of carbons in the chain
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How do you name simple cycloalkanes?
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add the prefix cyclo- to the name of the acyclic alkane that has the same number of carbons.
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The name of every organic molecule has 3 parts. What are they?
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1. parent name
2. suffix 3. prefix |
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what does the parent name tell you about an organic molecule?
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the number of carbons in the longest continuous carbon chain in the molecule.
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what does the suffix tell you when naming an organic molecule?
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the functional group that is present in the molecule.
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what does the prefix tell you when naming an organic molecule?
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the identity, location and number of substituents attached to the carbon chain.
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what do you call carbon constituents that are bonded to a long carbon chain?
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alkyl groups
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how are alkyl groups formed?
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by removing one hydrogen from an alkane
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how do you name an alkyl group?
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change the -ane ending of the parent alkane to -yl
(ex: methane CH4 become methyl CH3) |
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what complicates the naming of alkyl groups?
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the question of whether a primary or secondary hydrogen is removed!
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when a primary hydrogen is removed the prefix is ....
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nothing
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when a secondary hyrdogen is removed the prefix is......
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iso-
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how are cycloalkanes named?
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by the addition of the prefix cyclo-
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when an alkane is composed of a ring and a chain what determines whether a compound is named as an acyclic alkane or a cycloalkane?
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if the number of carbons in the ring is greater than or equal to the number of carbons in the longest chain, the compound is named as an cycloalkane.
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in conventional mass spectrometry, what is being detected?
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the molecular weight is what is detected, it is used to determine the molecular formula
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what is infrared spectroscopy for?
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to identify a compound's functional groups
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what do you call the tallest peak in a spectrum?
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the base peak
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what are the two regions that the IR spectrum is divided into?
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the functional group region and the fingerprint region
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where does the functional group region occur in an IR spectrum?
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equal to or > 1500cm^-1
(1500 or more) |
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where does the fingerprint region occur in an IR spectrum?
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equal to or <1500cm^-1
(1500 or less) |
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in MS when the molecular ion consists of two peaks (M and M+2) in a 3:1 ratio, what atom is present?
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Cl (chlorine)
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in MS when the molecular ion consists of two peaks (M and M) in a 1:1 ratio, what atom is present?
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Br (bromine)
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what is an isotope?
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the term "isotope" is used to refer to different forms of the same element that have different numbers of neutrons in the nucleus.
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what is the relationship between %s character, bond strength and wavenumber of absorption?
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The higher the %s, the stronger the bond, the higher the wavenumber of the absorption is
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what are the 3 fossils fuels?
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natural gas, petroleum and coal
and they all have different compositions of hydrocarbons |
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what is petroleum?
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complex mixture of compounds, mostly hydrocarbons with 1-40 carbons (gasoline, kerosene, diesel fuel)
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what is natural gas?
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composed mostly of methane with lesser amounts of butane, ethane and propane
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what is coal?
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a very complex mixture of compounds. many have aromatic rings that are linked together.
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what order are fuel oil, kerosene and gasoline arranged according to boiling point?
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highest bp= fuel oil, then kerosene, then gasoline=lowest bp
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how can you determine relative boiling points of petroleum products?
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boiling point increases as the number of carbons increases. if the number of carbons is the same then boiling point decreases with chain-branching.
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what do alkanes contain?
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only nonpolar c-c and c-h bonds
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what kind of forces occur between alkane molecules?
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only weak VDW
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are alkanes usually water soluble?
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no
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what is stereochemistry?
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the study of 3-d structures of organic molecules
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where does the rotation occur in acyclic alkanes?
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around c-c sigma bonds
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what are conformations?
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the different arrangement of atoms as they rotate around a single bond.
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what happens if you rotate one carbon by 60 degrees?
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an eclipsed conformation is converted into a staggered conformation and visa versa.
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what is a dihedral angle?
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the angle that separates a bond on one atom from a bond on an adjacent atom.
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what is a newman projection?
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a graphic that shows the three groups bonded to each carbon atom in a particular c-c bond, as well as the dihedral angle.
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which conformation is more stable?
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staggered is more stable than eclipsed (because staggered conformation is lower in energy)
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what causes the eclipsed conformation to be less stable than the staggered conformation?
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electron-electron repulsion between the bonds
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"more stable" means what in terms of energy?
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lower in energy
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"less stable" means what is terms of energy?
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higher in energy
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each eclipsed c-h bond results in an increase of energy by how much?
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1 kcal/mol
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what is the energy difference between staggered and eclipsed conformations called?
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torsional strain
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which conformation introduces torsional strain into a molecule?
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eclipsed
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by how much more is the staggered conformation more stable (lower in energy) than the eclipsed?
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by about about 3 kcal/mol
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what does strain result in?
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an increase in energy
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in an energy/rotation diagram how often do an energy minimum and maximum occur?
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every 60 degrees
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how many 60 degree rotations does it take to return a conformation of butane to it's original conformation?
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six
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what do you call a staggered conformation with two larger groups 180 degrees from each other?
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anti
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what do you call a staggered conformation with two larger groups 60 degrees from each other?
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gauche
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what are the two types of staggered conformations?
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anti and gauche
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what is steric strain?
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an increase in energy that results when atoms are forced to close to each other
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as a result of steric strain, which conformation is generally higher in energy than the other?
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gauche is generally higher in energy/less stable than anti because of steric strain
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can steric strain also affect the relative energies of eclipsed conformations?
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yes
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staggered conformations fall where on energy/dihedral angle graph?
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at the energy mimima
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eclipsed conformations fall where on energy/dihedral angle graph?
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at the energy maxima
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what effect to steric interactions have on energy?
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steric interactions increase energy (make less stable)
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what is the energy increase of an eclipsed H-H?
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1
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what is the energy increase of an eclipsed H-CH3?
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1.5
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what is the energy increase of an eclipsed CH3-CH3?
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4
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what is the energy increase of gauche CH3 groups?
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0.9
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what do you call the energy difference between the lowest and highest energy conformations?
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the barrier to rotation
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any acyclic alkane has what conformation when at it's lowest energy (most stable) conformation?
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all bonds staggered and anti (zig zagged)
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what is the highest possible energy conformation?
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eclipsed, with the two largest groups eclipsed
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what is the lowest possible energy conformation?
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staggered with the two largest groups anti
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what is angle strain?
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angle strain is an increase in energy when bond angles deviate from the optimum tetrahedral angle of 109.5
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are cycloalkanes with more than 6 C's flat?
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no, they are puckered to reduce torsional strain and angle strain
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what is torsional strain?
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strain caused by eclipsing interactions
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what is steric strain?
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strain produced when atoms are forced too close to each other
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what's the most commonly occurring ring size in naturally occurring compounds?
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cyclohexane (6 c-ring)
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why does cyclohexane adopt the chair formation?
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because this puckered chair formation allows all the hydrogens on adjacent carbons to be staggered (so no torsional strain) and all the c-c-c bond angles are 109.5 (so no angle strain)
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what are the two different kinds of hydrogens that each carbon has in cyclohexane?
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axial and equitorial
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what are axial hyrdogens?
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axial hydrogens are located above and below the ring
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what are equatorial hydrogens?
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equatorial hydrogens are located in the plain of the ring
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cyclohexane has how many up and how many down c's?
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3 up c's and 3 down c's alternate to "pucker"
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in ring-flipping of a cyclohexane, what constitutes the "boat" form?
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when a down carbon flips up
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what happens during a ring flip?
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all up c's become down c's and visa versa AND all equatorial h's become axial h's and visa versa
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how much more stable are the chair forms of cyclohexane than the boat forms?
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7 kcal/mol
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what types of strain are present in the boat formation?
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torsional & steric. torsinal because the hydrogens on bottom are eclipsed and steric because the ones on top (flagpole) are forced together
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what is general rule in terms of size of substituent and stability of cyclohexane? that is, in which form is the substituent more stable?
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the equatorial position, because it has more room making larger substituents more stable there.
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the larger substituent group on the cyclohexane is more stable where??
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in the equatorial position!
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what occurs when large substituents are axial in a chair formation?
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unfavorable 1,3-diaxial interactions
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the larger the substituent on the six-membered ring, the higher the percentage that the conformation will be what at equilibrium?
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equitorial
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what effect does a bulky group like tert-butyl have on the cyclohexane ring?
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it practically anchors it into the most stable conformation (with the tert-butyl in the eq. position)
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true or false: a group on one side of any cycloalkane ring can flip to the other side of the ring
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FALSE- a group on one side of any cycloalkane can NEVER rotate to the other side
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because groups on one side of a cycloalkane can never rotate to the other side, two different prefixes exhist to denote the two isomers. what are they?
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cis and trans = cis when the ring is disubstituated on the same side and trans when the two groups are or different sides
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what do all cycloalkanes with two groups bonded to different atoms have?
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cis and trans isomers
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on a disubstituated cyclohexane are the 2 different conformations for trans-isomers equally stable?
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no, the conformation where they are both equatorial will be most stable (as opposed to the one where they are both axial)
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on a disubstituated cyclohexane are the 2 different conformations for cis-isomers equally stable?
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yes, they exist in 50:50 ratio because they both have one equatorial and one axial
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in alkanes, what does oxidation result in?
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oxidation results in an increase of c-z bonds, and a decrease in c-h bonds.
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in alkanes, what does reduction result in?
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reduction results in the increase of c-h bonds, and a decrease in c-z bonds.
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are alkanes highly reactive?
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no but they do undergo combustion.
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what kind of rxn is combustion?
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red-ox
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oxidation is...
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loss of electrons
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reduction is...
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gain of electrons
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what is stereochemistry?
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the 3-d structure of a molecule
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are human hands chiral or achiral?
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chiral
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what does the word chiral mean in the literal sense?
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"hand" (i.e. handedness)
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what are isomers in the broad sense?
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different compounds with the same molecular formula.
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what are the two major classes of isomers?
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structural (aka constitutional) and stereoisomers
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what are some ways in which constitutional constitutional isomers differ?
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-have different iupac names
-the same or different functional groups -different physical properties -different chemical properties |
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what are some ways in which stereoisomers differ?
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-differ only in the way atoms are oriented in space
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do stereoisomers have the same or different iupac names?
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the same* (except for prefixes such as cis or trans)
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do stereoisomers have the same functional groups?
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yes! always... stereoisomers differ only in the way their atoms are oriented in space!
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what do you call a particular 3-d arrangement of atoms?
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a configuration
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what kind of isomer would have the same molecular formula with different names?
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constitutional
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what kind of isomer would have the same molecular formula with the same name(except for the prefix)?
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stereoisomer
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a molecule that is achiral is...
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superimposable on it's mirror image
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a molecule that is not superimposable on its mirror image is said to be...
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chiral
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are socks achiral or chiral?
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achiral- they can be superimposed upon one another
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are hands achiral or chiral?
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chiral- they cannot be superimposed upon one another
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what is an important rule regarding chirality when a molecule has four different groups attached to the center carbon?
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a molecule with four different groups attached to the center carbon is always chiral!
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what are enantiomers?
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mirror images that are NOT super imposable - therefore, that ARE chiral!
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what do you call the carbon atom that has four different groups bonded to it?
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a tetrahedral stereogenic center
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a molecule with no stereogenic centers is generally...
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not chiral (it IS achiral, and thus, superimposable)
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a molecule with one tetrahedral stereogenic center is....
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always chiral!
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a molecule with two or more stereogenic centers...
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may or may not be chiral
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what is a plane of symmetry?
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a mirror plane that cuts a molecule in half, so that one half of the molecule is a reflection of the other half.
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what type of molecules usually contain a plane of symmetry?
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achiral
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what type of molecules usually do not contain a plane of symmetry?
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chiral
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the presence of a plane of symmetry makes a molecule what?
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achiral
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what must a chiral molecule have?
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one or more stereogenic centers
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any molecule that has a stereogenic center is a chiral compound that exists a pair of what?
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enantiomers
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for 'n' number or stereogenic centers, what is the maximum number of stereoisomers?
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2^n (2 raised to the number of stereogenic centers)
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what are diastereomers?
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stereoisomers that are not mirror images
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what is a meso compound?
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an achiral compound that contains tetrahedral stereogenic centers
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what do meso compounds typically possess?
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a plane of symmetry
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the chemical and physical properties of two enantiomers are identical in every way except what?
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they differ only in their interaction with plane polarized light and chiral substances!
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do two enantiomers have identical physical properties?
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yes! same melting point, boiling point, solubility....except with how they interact with plane polarized light
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what is plane polarized light?
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passing light through a polarizer only allows light in one plane to pass through. this is polarized light. regular light consists of electromagnetic waves that oscillate in ALL planes perpendicular to the direction in which the light is traveling. plane polarized light only oscillates in a single plane.
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what is a polarimeter
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an instrument that allows plane polarized light to travel through a sample tube containing an organic compound
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what effect do achiral compounds have on plane polarized light as it travels through a polarimeter?
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the plane polarized light exits the sample tube unchanged.
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what do you say about a compound that does not change the plane of polarized light?
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it is "optically inactive"
(achiral molecules are optically inactive!) |
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what effect to chiral compounds have on plane polarized light as it travels though a polarimeter?
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the plane polarized light is rotated at an angle.
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what do you call the angle at which the plane polarized light is rotated by a chiral organic sample?
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observed rotation
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what does it mean for a compound to be "optically active?"
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that it rotates plane polarized light
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what are the two directions that plane polarized light can be rotated by a chiral, optically active compound?
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clockwise (dextrorotatory), or counter clockwise (levorotatory)
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does any relationship exist between R and S prefixes and the direction that PPL is rotated by an optically active compound?
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NOOOO
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how do two enantiomers rotate plane polarized light?
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to the same extent, but in the opposite direction!
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because two enantiomers rotate PPL to an equal extent, but in opposite directions, what must be true when there is an equal amount of both enantiomers??
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the rotations cancel! and no rotation is observed.
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what is the term used to describe the situation in which there is an equal amount of two enantiomers and the rotation cancels?
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a racemic mixture
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is a racemic mixture optically active or optically inactive?
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optically inactive (because the rotations cancel)
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are the physical properties of a racemic mixture the same as the properties of the enantiomers separately?
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no! the racemate of the two enantiomers can actually be different from the two on their own (even though THEY are the same)
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what is specific rotation?
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a physical property just like mp or bp that is defined by a formula that incorporates sample tube length, the observed rotation, concentration, temperature and wavelength emitted by a sodium light.
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what is enantiomeric excess? (ee)
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when there is neither a pure enantiomer, nor a racemic mixture, but rather a mixture of the two enantiomers in unequal amounts.
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enantiomeric excess (ee) is also called what?
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optical purity
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are the physical properties of a pair of diastereomers identical?
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no, they are are not mirror images so they have different physical properties including optical rotation
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can two enantiomers be separated by common physical techniques like distillation?
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no, because they have identical physical properties.
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can two diastereomers be separated by common physical techniques like distillation?
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yes, because they have different physical properties that distinguish themselves from one another.
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can two constitutional isomers be separated by common physical techniques like distillation?
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yes, because they have different physical properties that distinguish themselves from one another
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two enantiomers have identical physical properties except for what?
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their reaction with chiral, non-racemic reagents
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what are the three types of organic reactions discussed in ch. 6?
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substitution, elimination and addition
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what takes place during a substitution reaction?
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an atom or group of atoms is replaced by another atom or group of atoms
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what takes place during an elimination reaction?
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elements of the starting material are "lost" and a pi bond is formed (2 sigma bonds are broken)
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what takes place during an addition reaction?
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elements are added to a starting material (a pi bond is broken and 2 sigma bonds are formed)
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what is the relationship between addition and elimination reactions?
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they are exactly opposite of one another
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when a pi bond is formed, what kind of reaction is said to have occurred?
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elimination
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when a pi bond is lost, what kind of reaction is said to have occurred?
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addition
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what is a one step reaction called?
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concerted
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what do you call a detailed description of how bonds are broken and formed as a starting material is converted to a product?
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reaction mechanism
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in a step-wise reaction (one that involves more than one step) what is starting material first converted into?
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an unstable intermediate called a "reactive intermediate"
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how many different ways are there to cleave (break) a bond?
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only 2
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what are the only two ways that a bond can be cleaved?
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equally (homolytic cleavage) or unequally (heterolytic cleavage)
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when a bond is broken through heterolytic cleavage how do you know where the electron pair ends up?
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the electrons go to the more electronegative atom.
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what cleavage generates uncharged reactive intermediates with unpaired electrons?
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homolysis (aka homolytic cleavage)
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what cleavage generates charged intermediates?
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heterolytic cleavage
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through what type of cleavage is a radical created?
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homolysis
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through what type of cleavage are carbanions and carbcations created?
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heterolysis
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what is a radical?
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a reactive intermediate with one unpaired electron
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how many electrons surround a carbocation?
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6
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what is the charge on a carboanion?
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negative
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is a carboanion a nucleophile or an electrophile?
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nucleophile (contain carbon with lone pair)
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is a carbocation a nucleophile or an electrophile?
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electrophile (contain e- deficient carbon)
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is a radical a nucleophile or an electrophile?
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electrophile (contain e- deficient carbon)
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what always happens when bonds are formed?
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energy is released
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what is always required to break a bond?
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energy
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what is bond dissociation energy?
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the energy required to homolytically cleave a covalent bond
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form radicals!
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what is delta H?
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enthalpy change, or heat of reaction
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what does it mean when deltaH is positive?
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energy is absorbed and the reaction is endothermic
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what does it mean when deltaH is negative?
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energy is released and the reaction is exothermic
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are bond dissociation values positive or negative?
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always positive because bond breaking always requires energy
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the stronger the bond, the _____ it's dissociation energy
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higher
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what does it mean when deltaH is positive?
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that more energy is needed to break the bonds than is released in forming bonds. the bonds broken in the starting materials are stronger than those formed in the products (endothermic)
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what does it mean when deltaH is negative?
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more energy is released in forming bonds than is needed to break them. the bonds formed are stronger than the bonds broken in the starting material. (exothermic)
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what does kinetics describe?
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reaction rate
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do fast reactions have large or small rate constants?
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large
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do slow reactions have large or small rate constants?
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small
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with a high Ea, does a reaction go slower or faster?
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slower
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an increase in temperature has what effect on the rate of a reaction?
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speeds it up
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how does a higher concentration effect rate of reaction?
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the higher the concentration the faster the rate
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what's a rate determining step?
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the slowest step in the reaction (the step with the HIGHEST energy transition state)
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what are the important properties of a catalyst?
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-speed up rate of reaction
-is unchanged in rxn -does not appear in products -lowers the Ea |
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enzymes are naturally occurring what?
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catalysts
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what effect does Keq have on reaction rate?
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NONE. keq does not effect reaction rate!
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what effect does deltaH have on reaction rate?
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none
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does deltaG, deltaH or Keq effect rate of reaction?
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NO
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on an energy diagram what is deltaH?
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the difference between REACTANTS and PRODUCTS
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on an energy diagram what is the Ea?
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the difference between the TRANSITION STATE and the REACTANTS
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