Organic Chemistry 9 Flashcards

Terms Definitions
amide
O=CN
halo
halogeno's
CH3CH3
ethane
CH3CH2
Ethyl
Gauche
lipid
...
carboxyl
organic acids
linear angle
180
lewis acid
...
x
2-hydroxybenzoic acid
5
How many carbons-Pentyl
Alkenes
double bonds
Cn H2n
Lysosomes
Have hydrolytic enzymes.
Alkyne
structural element C≡C
Organic
Derived from living organisms
carbohydrate
used for short-term energy
aldehyde
functional group, carbonyl, -COH
Ethyl
The -CH2CH3 alkyl group
carbocation
A positively charged carbon
DNA
deoxyribonucleic acid, the material that contains the information that determines inherited characteristics
Every carbon must have
Four bonds
non-
9 carbons in the skeleton
alkane
C n H 2n+2 implies
structural isomers
differ in atomic arrangement
cyclic hydrocarbon
hydrocarbons form a ring
conformers
constantly changing the geometric relationship of the hydrogens on one carbon with those on the other.
ethers
two carbons bonded to same oxygen
co-enzyme
vitamins and minerals that help enzymes to function
transport
Function of protein: oxygen movement in red blood cells
natural polymer
important types of biological molecules
intermolecular attraction
occur due to dipole moments
Types of bonds in Organic Compounds
Covalent
Glycerol
used for sweetening and preserving food, obtained from animal fats and oils or by the fermentation of glucose
diastereomers
stereoisomers whose molecules are not mirror images of each other - e.g. cis/trans isomers
secondary and tertiary ethers form alkenes
macromolecule
Carbohydrates are a type of __________.
Carboxyl Group
COOH, carbon double-bonded to oxygen and single-bonded to hydrogen
fats
large molecules made of glycerol and fatty acids
neutral
H+ and OH- ions the same; pH=7
EST
Esterification (Alcohol -OH + Acid =O & -OH)
Phosphate
P surrounded on 4 sides by O
protein tertiary structure
overall 3D shape of protein
CH₃COCl, pyridine
Turns aniline into benzene with NHAc
alkane combustion
O2 --> CO2 +H2O + energy
dialcohol
Under mild conditions, oxidation of an alkene by potassium permanganate will lead to a...
Aryl carbon-carbon bonds
show absorption slightly lower frequencies (to the right in the spectrum)
Amides
like esters (double bond oxygen adj. to carbon) with a Nitrogen; Functional group; Peptides; Side chains + Prefix + "amide"
What is the general formula for hydrcarbons?
CnH2n
Polysaccharides
long chains of simple sugars linked together by dehydration synthesis
SDS-PAGE
separates proteins on basis on the basis of mass, not charge. When pH =pI, the protein stops moving.
A hydrocarbon that has one or more hydrogen atoms replaced by atoms of a halogen (chlorine, fluorine, or iodine)
haloalkanes
carbon triple bonded to nitrogen is called
schiff's base
inorganic compound
any compound that does not contain carbon-carbon bonds
when peptide bonds join it creates what?
polypeptide chains
Resonance
differ in the position of the Pi bond(s) or lone pair(s).
sp3- bond angles and shape
109.5 tetrahedral, pyramidal, bent
Skeletal structural formula
structural formula that shows the arrangement and bonding of carbon atoms present in an organic molecule but does not show the hydrogen atoms attatched to the C atoms.
markownikoffs rule
the major product formed by the addition of an unsymmetrical reagent sich as HCl or HBr is the one obtained when the H atom of the reagent adds to the carbon atom of the miltiple bond that already has the greater number of hydrogen atoms attached to it
Molarity
# of moles of solute dissolved per liter of solution.
1,2-Shift
A type of rearrangement in which an atom or group of atoms with its bonding electrons moves from one atom to an adjacent electron-deficient atom
Unsaturated alcohols
Compounds containg -OH and C=C groups are often referred to as this because of the presence of the carbon-carbon double bond
Conformational Isomers (Conformers)
Different conformations that have long bough lifetimes to be characterized are often called this?
Lindlar's catalyst
poisons the double bond so that the process can only occur once and the alkene of a hydrogenation reaction can be collected.
Halides / Halocarbons
General Formula R-X(where x can be -Cl, I, F, Br) Name of prefix: chloro----(drop -ine, add -o)
dehydration synthesis
process in which water is removed to build larger molecules
geometric isomer
exist due to hindered rotation about a bond- due to ring structure, double or triple bond, can be cis or trans isomers, have different physical properties
structural formulas (arrangement)
a chemical formula showing the spatial relationship between the substituent atoms in the molecule
halocarbon
a hydrocarbon that has had one or more halogen atoms substituted or added to the carbon chain
unsaturated compound
An organic compound with at least one double or triple bond between carbon atoms is called a(n) ________.
Hooke's Law Reduced Mass Term
Atomic masses; vibrations b/t light/heavy atoms = higher wavenumber than b/t heavy atoms.
DEPT (Distortionless Enhanced Polarization Transfer)
A method of running several 13C experiments with different pulse sequences so that the carbon atoms appear differently depending on whether they are bonded to 0, 1, 2, or 3 protons.
secondary protein
Winding of an amino acid chain into a helix or pleated sheet
chiral carbon
a carbon that is bonded to 4 different groups
Non-polar solvent
A solvent is a non-polar solvent if it has a dielectric constant of less than 5 (solvents with a dielectric constant between 5 and 15 are borderline)
what are the physical properties of the following?
methane- CH4ethane- C2H6propane- C3H8butane-C4H10
heterolytic cleavage
the breaking of a bond in such a way that one of the atoms retains both of the bond's electrons. a heterolytic cleavage forms two ions
Aprotic solvents and SN2 reactions examples of good solvents and why they are good
DMF, DMSO, DMA, HMPAthey dissolve ionic compounds and solvate cations very wellNOTE aprotics solvents do not solvate anions to an appreciable extentAprotic solvent trends for halide nucleophilicity strongest to weakestF>Cl>Br>I
what does an amino acid consist of?
1 carboxyl group(COOH), 1 amino group(NH2), 1 hydrogen atom, and one side chain
how to find major contributor of resonance hybrid
1. more covalent bonds 2. smaller separation of opp. charged atoms 3. neg charge on the most e- atom
What is the trend associated with the H-A bond strength?
The weaker the H-A bond the stronger the acid.
Hydroboration/oxidation-mechanism
(alkenes)
...
amine
R-NH2
Epoxidation
N/A
Ether
-O-
e.c.
amino, amine
amines
ketone
O
||
R-C-R
alcohol group
oh
6 carbons
hex
Alkene hydration (reactants)
H2O
meth
prefix for one
Sucrose
glucose plus fructose
conformer
a conformational isomer
Addition Rxn- general rxn
(alkenes)
...
3 Carbon atom prefix
prop
HDL
High density lipoproteins; "good."
Hydroboration Oxidation of Alkynes
1.)BH3
----------->
2.)H2O/NaOH

Anti-Markovnikov
terminal alkynes=aldehydes
internal alkynes=keytones
no rearrangements
valence shell
an atom's outermost shell
cyclic
containing a ring of atoms
Acetal
Hemiacetal + Alcohol + Acid
doublet
means there is one hydrogen
CH
Electrophile
Positively polarised electron seeking groups
during Sn2 relative configuration is
inverted
disaccharide
2 monosaccharides joined together thru dehydration
preservative
Paraformaldehyde is used in embalming as a
Cellulose
plant's structural material, tough and insoluble, in plant walls
phospholipid
makes up the membranes in cells
Alkanes
Hydrocarbons that only contain single bonds.
esterification
the process of making an ester
Anti-aromatic
have electron in higher energy nonbonding or antibonding; fits all condition except hucke's rule
IUPAC
International Union of Pure and Applied Chemistry
Lactose
a disaccharide that upon hydrolysis yields glucose and Galactose. C12H22O11
Bacteriophage DNA is transcribed to mRNA during the ??? phase of viral replication.
SYNTHESIS
cofactor
Any non-protein molecule or ion that is required for the proper functioning of an enzyme. Cofactors can be permanently bound to the active site or may bind loosely with the substrate during catalysis. Ex. Fe, Zinc, Cu, Mn
isomer
compounds with the same simple formula but different three-dimensional structures resulting in different physical and chemical properties
polymer
large molecule made up of smaller building blocks or monomers
monomers
Polymers are made of smaller units called __
Racemic mixture
2 enantiomers synthesized in chemical reaction in same quantities
A synthetic compound similar to soap capable of cleansing even in hard water
detergents
Aromatic hydrocarbons
have special stability due to delocalization of pi electrons
hydrogenation
alkene/alkyne + hydrogen + pressure + (Ni, Pd, Pt, Ru, Rh) produce alkane
triple bond
six electrons (three pairs) are shared
is leaving group always more tstable than the nucleophile?
yes
Reducing Sugar
Possesses functionality that is easily oxidizable (hemiacetal, aldehyde).
Ar-alkyl in NMR
slightly broadened singlet
5 hydrogen integration
how many electrons do anions have in the non-bonding orbital?
2
Naming Esters
They have 2 words:1st: alkyl (-yl) attached to single bonded oxygen2nd: add -oate to the other hydrocarbon chain
carbon
essential to life and makes up the backbone of organic molecules
gauche conformation
a conformation with a 60 degree dihedral angle between the largest groups
deoxyribonucleic acid
-found in the nucleus of cells
-codes for protien synthesis
-double helix structure
what is chitin used for?
hard shell on insects.
Waxes
Fatty acids bonded to an alcohol. One strait chain. More hydrophobic than fats
Alcohols
Have a carbon atom bonded to the oxygen of a hydroxyl group (-OH).
Hammond Postulate
Exothermic rxn (lose energy) = early TS (more similar to reactants); endothermic rxn (gain energy) = late TS (more similar to products).
E2 reactions
can occur with primary, secondary, or tertiary halidesgood leaving grouphigher temperaturesNOT FINISHED
Chemoselective reaction
a reaction in which a reagent reacts with one functional group in preference to another
Ethyl Mercaptan
The chemical that is added to natural gas to give it a distinct odor
compounds with C, H, N, maybe O
amines, nitriles, amides
substituents
atom or group of atoms that forms the branch
torsional strain
the strain in a molecule caused by electron repulsion between eclipsed bonds
IUPAC system (5)
5. When two substituents are present on the same carbon atom, use that number twice.
alpha beta unsaturated carbonyls undergo
enol-keto tautomer with nucelophile beta
Physical Properties of Carboxylic Acid
OH∴ hydrogen bonding∴H₂O soluble up to the ratio 4/5C per CooH
The HIGH Polarity makes the BP HIGH as well B/C there are 2 cites for h-bonding
unsymmetrical bond formation
both e- donated by one of the reactants
Oxidation of secondary alcohol reagents
PCC or CrO3 or HCrO4- resin
chemical shift
units of ppm and is on the x axis
Radical Propagation Sequences (Catalytic Cycle)
Ex: Initiation forms Br; attacks CH4 for HBr and CH3 radical; attacks BR2 for more Br; continuous process, ex. ozone depletion.
Boron Trihalides have an unoccupied
p orbital which will readily grab water's electrons causing an explosion.
Carboxylic ester (or ester)
A derivative of a carboxylic acid in which H of the carboxyl group is replaced by a carbon
Restrictions on the use of grignard reagents
avoid:
1. alcohols
2. 1° and 2° amines
3. carboxylic acids
4. -S-H
5. terminal alkynes
water
Molecular Hybrids and Relationship to VSEPR
1. Hybrid atomic orbitals are obtained by mixing the wave function for orbitals of different types (i.e. s and p orbitals) but form the same atom.
2. Hybridizing three p orbitals with one s orbital yields four sp³ orbitals. Atoms that are sp³ hybridized direct the axes of their four sp³ orbitals toward the corners of a tetrahedron.
3. Hybridizing two p orbitals with one s orbital yields three sp² orbitals. Atoms that are sp² hybridized point the axes of their three sp² orbitals toward the corners of an equilateral triangle.
4. Hybridizing one p orbital with one s orbital yields two sp orbitals. Atoms that are sp hybridized orient the axes of their two sp orbitals in opposite directions (at an angle of 180°).
when do you have to worry about endo and exo products?
when you work with cyclic compounds
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