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functional groups
functional groups
61
Chemistry
Undergraduate 2
09/24/2008

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Term
Alkyl, and occasionally aryl (aromatic) functions are represented by the R-

Methyl: CH3–
Ethyl: CH3CH2–
Propyl: CH3CH2CH2–
Isopropyl: (CH3)2CH–
Phenyl: C6H5–
etc.
Definition
[image]
Term
Br : MS
Definition
M+2 peak is nearly as tall as m peak
Term
Cl : MS
Definition
M+2 peak is 1/3 of the size of M+ peak
Term
N : MS
Definition
has an odd # for their M+ peaks
Term
IR: high energy
Definition
high frequency
large wave#
short wave lengths
Term
intensity of bond
Definition
greater the charge in the dipole moment, more intense the absorption
-more polar the bond, the more intense it is
Term
IR characteristics
Definition
-cant determine structure alone
-some signals are ambiguous
-if there is an absence of a signal, thats definite proof that the function roups is absent
-look at the literature value of the compound to confirm or vice versa
Term
triplanar: degrees?
Definition
120 degress
Term
linear: bond angle?
Definition
109.5 degrees
Term
linear: bond angle?
Definition
180 degrees
Term
C-C :bond length?
Definition
1.54 A
Term
C=C: bond length?
Definition
1.34 A
Term
C=-C: bond length?
Definition
1.20 A
Term
condensed formula
Definition
CH3OCH3
Term
acid strength: down group
Definition
larger size differnce, weaker bond
Term
acid strength: across row
Definition
greater electronegativity, more polorized bond
Term
acid strength: c-H vs C-O
Definition
conjugate base is stablized by inductive and resonance effects
Term
acid strength: molecular weight
Definition
conjugate base is better stablized by inductive effects
Term
stronger bases than -OH put in water
Definition
leveling effect
-bases stronger than OH- will simply deprotonate water to form the weaker base OH-
Term
molecular weight
Definition
what is the main piece of information sought from analysis of a compound by low-resolution mass spectrometry?
Term
molecular formula
Definition
What is the main piece of information sought from analysis of a compound by high resolution mass spectometry?
Term
identification of functional groups
Definition
What is the main piece of information sought form analysis of a compound by infrared spectroscopy?
Term
-hexane
has a higher molecular weight and more van der waals interactions
Definition
higher BP: hexane vs pentane?
Term
-alcohol
can hydrogen bond to its neighbors
Definition
higher BP: ether vs alcohol
Term
1. ion charges
2. higher molecular weight
3. has halogen
Definition
most soluable in water?
Term
-more symmetrical
Definition
most inportant factor for higher MP?
Term
1. ion-ion, coulombic attraction
2. dipole-dipole attraction
3. hydrogen bond - typeof dipole-dipole
4. van der waals -transient dipole-dipole
Definition
explain 4 differnt types of bonds
Term
a gas chromotograph and a mass spectrometer
Definition
what two instruments are coupled together in a so-called GC-MS?
Term
compounds with ane ven # of nitrogenn
(or O) have an even molecular mass
compounds with an odd # of nitrogems have an odd molecular mass
Definition
explain what the nitrogen rule is
Term
the stretch produces no charge in the dipole moment
Definition
why cant the symmetrical stretch of carbon dioxide produce a peak (absorption) in a normal IR spectrum?
Term
H2O
has a greater propensity to donate a proton because the conjugate base (OH-) would be more stable than (NH2-) due to the more electronegative oxygen atom
Definition
which one is the stronger acid and why?
H2O vs NH3
Term
CH3CF2COOH
has a greater propensity to donate a proton because the conjugate base is more stable as a result of the more effective (-) charge delocalization due to stronger induction thru the sigma bonds by the more proximal F atoms
Definition
which one is the stronger acid?
F2CHCH2COOH vs CH3CF2COOH
Term
HCl
has a greater propensity to donate a proton becaus the conjugate base (Cl-) would be more stable than (F-) due to Cl- being larger and the negative charge being dispersed over a larger volume
Definition
which one is the stronger acid?
HF vs HCl
Term
CH=-CH
has agreater propensity to donate a proton because the conjugate base is more stable as a result of the lone pair residing in an sp orbital (as opposed to an sp3 orbital) which has more s character (50%), so the lone pair is in a lower energy, closer to the nucleus
Definition
which is the stronger acid?
CH3CH3 vs CH=-CH
Term
pie bonds and heteroatoms
Definition
in general, what are two structural features in organic compounds, any one of which, that give rise to so-called functional groups and useful reactivity?
Term
electromagnetic radiation
Definition
radient energy having dual properties of both waves anad particles
Term
photons
Definition
particles of electromagnetic readiation
Term
quantum
Definition
each photon has a discrete amount of energy
Term
wavelength and frequency
Definition
electrommagnetic radiation can be characterized by its:
Term
wavelength
Definition
the distance form one point on a wave to the same point on an adjacent wave
Term
frequency
Definition
the number of waves passing per unit of time, hertz
Term
true
Definition
t/F?
for absorption ot occur, the energy of the photon must match the difference between two energy states in a molecule
Term
IR radiation
Definition
the energy source used in IR spectroscopy
Term
true
Definition
t/f?
absorption of IR light causes changes in the vibrational motions of a molecule
Term
true
Definition
t/f?
IR spectroscopy distinguishes between the different kinds of bonds in a molecule, so it is possible to determine the functional groups present
Term
1. light passes through a sample
3. frequencies that match the vibrational frequencies are absorbed,and the remaining light is transmitted to a detector
3. an "IR spectrum is a plot of the amount of transmitted light versus its wavenumber
Definition
characteristics of IR:
Term
100% transmittance
Definition
that all the light shone on a sample is transmitted and none is absorbed
Term
0% transmittance
Definition
that none of the light shone on the sample is transmitted and all is absorbed
Term
true
Definition
t/f?
stronger bonds vibrate at a higher frequency, so they absorb at higher wavenumbers
Term
.
Definition
bonds with lighter atoms vibrate at higher frequency, so they absorb at higher wavenumbers
Term
.
Definition
the higher the percent s-character, the stronger the bond and the hgiher the wavenumber of absorption
Term
.
Definition
for a bond to absorb in the IR, there must be a change in dipole moment during the vibration
Term
IR inactive
Definition
symmetrical nonpolar bonds do not absorb in the IR
Term
.
Definition
IR spectroscopy is often used to determine the outcome of a chemical reaction
Term
.
Definition
i a mass spectrometer, a molecule is vaporized and ionized by bombardment with a beam ofhigh-energy electrons
Term
.
Definition
the electron beam ionizes the molecule by causing it to eject an electron
Term
radical cation, M+
Definition
when the elctron beam is ionized the molecule, the species that is formed is called?
Term
.
Definition
the mass of M+ represents the molecular weight of M
Term
.
Definition
because M is unstable, it decomposes to fomr fragments of radicaals and cations that have a lower molecular weight than M+
Term
.
Definition
the mass spectrum analyzes the masses of cations, a plot of the amount of each cation versus its mass to charge ratio
Term
.
Definition
when the sample is injected into the GC, it is vaporized and swept by an inert gas through the column and components are usually seperated by boiling points
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