Organic Chemistry 8 Flashcards

Terms Definitions
amino
amino
ene
double
keytone
RCOR
Alcohols
R-OH
Dodecane
C₁₂H₂₆
polysaccharide
...
phosphate
organic phosphate
tetrahedral angle
109.5
Benzene
simplest arene
x
2-isopropylcyclopentancecarboxylic acid
ol
prefix for alcohol
dipeptide
2 amino acids
-7.0
HCl + H2O
Ketone
C O C
cyclo
prefix for a ring
SUB
Substitution (Saturated molecules where you usually sub a halogen.) *Same # of atoms.
molecular handedness
chiral-mirror image isomers;
methyl ethyl ketone
airplane glue
Bronsted acid
A proton donor
Dehydrohalogenation
-removal of the elements HX
-alpha-carbon: the carbon bonded to the X
-beta-carbon: any carbon bonded to a alpha-carbon
-removal of a H on a beta-carbon results in beta-elimination
CnH2n+2
general formula for straight-chained and branced alkanes
but-
4 carbons in the skeleton
triple bonds
defining factor of alkynes
geometric isomers
differ in spatial orientation
free radical reaction
initiated by light
alkanes
c-c single bonds, saturated hydrocarbons(paraffins)
isomers
compounds with same molecular formula but different structures
starch
A storage polysaccharide in plants consisting entirely of glucose.
fats
lipid that storage for extra carbohydrates
organisms use __ as insulation
aromatic hydrocarbons
hydrocarbons with similar ring structures
isopropyl
CH3-CH-CH3 w/ connection at central C
Who has higher boiling points; continuous alkanes or cycloalkanes
cycloalkanes
meta
A substituent of a disubstituted benzene that is two down from the primary substituent
specific rotation of light
[α] = α/cl
a-d
alkoxymercuration adds the -OR group of the alcohol tot he more substituted carbon atom of the C=C bond
monomers
Repeating units in all organic compounds
Disaccharide
a double sugar, consisting of two monosaccharides joined by dehydration reaction
cholesterol
important steroid that is the basis for the formation of other steroids
chemical reaction
reaction where energy is often produced
Rule #4
Use prefixes for # of groups
chair conformation
the most stable conformation of cyclohexane, with one part puckered upward and another part puckered downward
carbonyl group
carbon atom double bonded to oxygen
HBF₄, 0°C or (delta)
DZ salt to florobenzene
alkene addition hydrogenation
H2--> (Ni, Pd, Pt) alkane
aryl
aromatic compound referred to as this, or arenes. Ar
Parent chain
The longest continuous chain of carbons in the molecule
Enzymes
globular proteins that act as a biological catalyst
Epimers
Differ in configuration only at one carbon
reduction reaction
the type of reaction that adds hydrogens to a triple or double bond.
oxygen bonded to two atoms or groups has_______ hybridization
sp3
fatty acid
with glycerol, make up the building blocks of lipids
amino acids form what kinds of bonds?
peptide bonds
Inductive Effect
described as the shifting of electrons in response to the electronegative of nearby atom
ester
R-COOR (Double bond between C and O with OR group connected to C also)
Emulsifier
Is a substance that can disperse and stabilize water-insoluble substances as colloidal particles in an aqueous solution.
unsaturated hydrocarbons
contain double or triple bonds; have less hydrogen atoms than a saturated hydrocarbon
Amide
A compound that has a carbonyl group bonded to a carbon atom and to a nitrogen atom group, RCONR2
Oxymercuration-reduction
A method for converting an alkene to an alcohol. The alkene is treated with mercury(II) acetate followed by reduction with sodium borohydride.
Amines via reduction
Reduction of nitro, nitriles, and amides. Use reducing agent LiAlH4, ether/H2O. CN gives a primary alylkamide with one more carbon. Can also use H2/Pt. Amide reduction gives the same amount of carbons. Can be used on primary, secondary, or tertiary amides. For the nitro, can use LiAlH4, H2/Pt, or Sn/H+. Will get a primary amine.
Trans
A prefix meaning across from (on the opposite side of the ring)
Properties of Alcohols
1)Like water, alcohols are capable of hydrogen bonding between molecules 2)this means they have a relatively high boiling point3) Somewhat soluble, in water
Hydrolysis
the addition of water to break a large molecule into smaller ones
enamine and its tautomer
R-C=CR2- NRH (enamine), tautomer is imine R-C(CR2H)=N-R
structural formulas (arrangement)
a chemical formula showing the spatial relationship between the substituent atoms in the molecule
Excited vibrational state
Nuclei of atoms bonded by covalent bonds undergo vibrations, or oscillations, in a manner similar to two balls attached by a string. when molecules absorb infrared radiation, the absorbed energy causes an increase in amplitude of the vibrations of the bonded atoms
primary alcohol
an alcohol that has one alkyl group bonded to the carbon atom with the -OH
Ring Fusion Carbons
Shared carbons in fused (two shared carbons) and spiro (one shared carbon) systems.
Off-resonance decoupling
a technique used with 13C NMR in which only the protons directly bonded to a carbon atom cause spin-spin splitting.
polar covalent bond
a covalent bond in which electrons are not shared equally
RL -> R+ + L-
First step in a SN1 reaction
reaction of williamson ether synthsis
-W.E.S. involves the Sn2 attack.
-secondary alkyl halides and tosylates are occasionally used in Williamson synthesis, but elimination competes, and yields are often poor.
-the alkoxide is commonly made by adding Na, K, or NaH to alcohol
what are the physical properties of ethenepropeneb
ethene- C2H4propance- C3H6butene- C4H8
homolytic cleavage
the breaking of a bond in such a way that each atom retains one of the bond's two electrons. a homolytic cleavage produces two radicals
Bimolecular vs Unimolecular
bi - 2 species involved SN2uni - 1 specie involved SN1
2 examples of polysaccharides that store energy
1. starch (plants store glucose as fat) 2. glycogen (animals store glucose as glycogen in the liver)
Why are alkanes the least reactive family of organic compounds
Because carbon to carbon single bonds are hard to break
What is the formula to calculate formal charge?
FC = Group # - (# unshared electrons - 1/2 # shared electrons)
prop
3
alkene
-ene
Hydroboration-Oxidation
Anti-Markovnikov
Ch2Ch3
ethyl
ethyl
-C2H5
e.c.
d orbital
sp3 HNMR
0-1.5
CnH2n
alkene formula
Carboxylic Acid
R-C=O(up)-OH
dehydration synthesis
forms fat
triglyceride
synonym for fat
Alkane
CnH2n+2, saturated, sp3
6 carbon atoms
hexane
Fructose
Levulose
-Fruit sugar
-Found in invert sugar(used in candy making)and honey
Polysaccharides
long chains of glucose
http://classconnection.s3.amazonaws.com/1498/flashcards/714083/jpg/halohydrin-formation.jpg
Halohydrin FormationWater competes with Bromide as a nucleophile. Exhibits anti-sterochemistry and regioselective. Water gets added to most substituted carbon. (2 H20 involved) H goes to less substitued.
pKa of ethanol
pKa = 17
Sucrose
glucose+fructose, transport form of sugar for plants, in our food
KI (25-100°C)
DZ salt to iodobenzene
triplet
means there is two hydrogens
CH2
carboxyl 13C NMR chemical shift
160-180
examples of williamson ether synthsis
-N or -NH or -NH2
amine
tertiary structure
irregular "folds" because of interactions between R groups
maltose
"sugar in beer;" is a disaccharide
isomerism
different arrangement of atoms between 2 or more molecules
arenes
special group of unsatureated cyclic HC
dialdehydes
an organic compuound containing two aldehyde radicals. 7 carbons
doublet
two peaks of identical inensity equally spaced around the true chemical shift.
PO4-2
phosphates-already got rid of H2, Energy transfer, acidic, polar, H2O soluble,
ozone and alkene
oxidation to two carbonyls
Friedel Crafts Acylation
Electrophilic aromatic substitution, acyl chloride plus a benzene ring.
pH --> H+
[H+] = 10 - pH
cis
the isomer in which the substituents are on the same side of the double bond or ring
carbohydrate
This organic compound has "rings" of carbon.
secondary structure
structure of protein: coiling of chain
Hydrocarbon
Made up of only Hydrogen and Carbon
thermodynamic product of enol
Na+ -OCH2CH3 and alcohol
alkenes
Hydrocarbons that contain at least one double bond between the carbons.
electronegativity
determine which atom is stronger; the measure of an atom's intrinsic ability to attract e-'s in a covalent bond
R group
a generalized abbreviation for an organic partial structure
hex
prefix for a chain of 6 carbons
double bond
four electrons (two pairs) are shared
TsCl
---------->
pyridine
SUBSTITUTES -OTs for -OH
- OH ---> OTs
Pericyclic Reactions
Four or more electrons transferred together w/o generating charge.
Organic acids
Replace hydrogen with carboxyl group (COOH)
-anoic acid
reagents needed for acid-catalyzed ring opening of epoxides
1. strong acid
2. water
How many bonds can a Carbon atom form?
4
Aromatic or Cyclic
Those compounds whose chains of carbons form a ring
dihedral angle
the angle between two specific groups in a Newman projection
protein quaternary structure
the association of the proteins subunits
cycloalkane
a saturated carbon chain that forms a loop or a ring
Constitutional isomers
Compounds which have the same formula but differ in the way their atoms are connected.
active site
part of an enzyme that controls chemical reactions
acidic or basic proteins
carboxylic acids= acidic, amines= basic
stereocenter
An atom about which exchanged of two groups produces a stereoisomer. Chiral centers are one type of stereocenter
Reduction of Aldehydes and Ketones to Alcohols Reagents? Reduce All?
 
1)LiAlH4, Et2O
2)H2O
 
NaBH4
MeOH
Rosenmund Reduction
The reduction of an acyl chloride can be stopped at an aldehyde if H2/partially deactivated Pd is used
Putrescine and Cadaverine
the two diamines relating to funeral services.
types of hydrocarbons (C & H)
alkane, alkene, alkyne, aromatic
enthalpy
a measure of the heat energy in a system. in a reaction, the heat absorbed or evolved is called the heat of reaction. a decrease in enthalpy is favorable for a reaction
steric strain
the strain imposed on a molecule when two groups are too close together and try to occupy the same space
formaldehyde
An aldehyde where the R group is a hydrogen
imine product always exists as
tautomer with a coresponding enamine
Radical substitution
Initiation: Cl-Cl + UV light -> Cl○ + ○Cl
Propogation: CH4+ Cl○ -> CH3○ + H-Cl
Radical forms more easily on more substituted carbons
CH3○+ Cl-Cl -> CH3Cl + Cl○
Termination: Cl○ + Cl○ or CH3○ + ○CH3
sp3 s can't be involved with double bonds because no p orbitals are available for
a pi bond
covalently, carbon atoms, organic compounds
functional groups: lone atoms or clusters of atoms that are _______ bonded to _______ of __________.
Sp hybrid orbital
a hybrid atomic orbital formed by the combination of one s atomic orbital and one p atomic orbital; bond angles of approximately 180degrees; 2 pi bonds
Williamson Ether Synthesis
Alkoxide Nuc removes LG via SN2 to form ether.
Regioselectivity and Reactivity in E1 Reactions
The E1 reaction is regioselective (major produced more sub): ;like E2 reactions; the major product is typically the more substituted alkene, and Zaitsev's rule usually applies.
With the same alkyl group, relative reactivities are determined by leaving group ability (weaker base better):
-RI>RBr>RCl>RF
grignard reagent + CO2 ->
carboxylate salt (add H+ to form COOH)
reaction of a diene with HX at 40°C wil give what kind of addition as the major product?
1,4 addition (thermo addition)
Linear Combination of Atomic Orbitals (LCAO)
Adjacent p orbitals can be combined; "pi" bonds (addition), nodes (subtraction).
What are the important principles of VSEPR?
1. Electron pairs in carbon always form at tetrahedral angles.2. Molecular shape dependent upon the bonded atoms and NOT their unshared pairs.
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Term:
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