Organic Chemistry Test 2 Flashcards

Terms Definitions
Ethane
C2H6
octane
8
imidazole
1,3-diazacyclopenta-2,4-diene
Glycine
-Gly
Monophosphate
phosphate
configuration
...
Dihalogenation- mechanism
(alkenes)
...
Ethers
-O-
R-O-R'
Alkenes
CnH2n Non-polar
(Z) RCH=CHR
675-730
Gay-Lussac
P1/T1 = P2/T2
alkenes can form?
polymers
IUPAC name: CH3-CH3-Br
Bromoethane
(ether) -oxy/ether
R-O-R (9th)
Nucleic Acid polymers
DNA RNA
RNA (RiboNucleic Acid)
makes proteins
IUPAC
precise internationally accepted system of naming organic compounds
amines behave as a
base
Lipids
Hydro____
Why?
Macros?
Hydrophobic-
hydrocarbons (neutral) and oxygen used to build it.
insolable in water, dissolve readily in non-polar solvents
No- no repeating monomers
sp
-c=-n: or -c=-c- 180 linear
Hydrocarbon 1
Methane (Natural gases) CH4
Organic Chemistry
study of carbon compounds
pent-
IUPAC prefix for 5 carbons
aldehyde/ketone MS fragmentation
a-cleavage, McLafferty rearrangement
Alcohols
organic compounds containing hydroxyl groups
Dextero-rotary
Optically active molecule which rotates plane polarized light in clockwise direction (+).
hydrolysis
the decomposition of organic compounds by interaction with water, maltose+water= glucose+glucose -reverse effect of dehydration
What reaction takes place when Hydrogen is lost and oxygen is gaines
Oxidation
Tertiary, Main reactions with poor nucleophiles/weak bases
SN1/E1
acetates in mass spec
peak at 59
Excess Br₂, 0°C, CCl₄
Bromination of benzene
cellulose
structural polysaccharide also made of glucose used in sell walls, form fibers
single covalent
Alkanes have only ___ bonds.
lactose
milk sugar. glucose + galactose. digested to glucose and galactose, important in infant nutrition.
maltose
glucosidic linkage of two glucose molecules
CARBS!
Sugar & Related Compounds
CH2O Carbon plus Water
amino acid
organic compounds containing an amino group and a carboxylic acid group
When nitrogen is bonded to three different atoms or groups, it's hybridization state is
sp3
pH scale
measurement system used to indicate the concentration of hydrogen ions (H+) in solution; ranges from 0 to 14
Macromolecules
Large molecules made up of carbon chains
irritability
excessive sensitivity of an organ or body part
active site
where the reactant enters the enzyme
aldol condensation
two aldehydes reacting, two ketones reacting or an aldehyde reacting with a ketone
ketone
an organic compound in which a carbonyl group is attached to two alkyl groups; obtained by the oxidation of secondary alcohols
The chitin monomer
has an attached amino group
Acylation
The process of introducing an acyl group into a benzene ring
Halogenated Hydrocarbons
Hydrocarbons with one or more hydrogens replaced with
chlorine or fluorine
• Non-miscible with and generally more dense than water
alkyne
a colorless flammable gas used chiefly in welding and in organic synthesis
carboxylic acid
A molecule containing a carboxyl (COOH) group. Also a functional group.
Reagents to organometallies with carboxylic acid derivatives?
 
R-M (2eq)
Then NH4Cl
 
(M=MgBr)
Kinetic product
Controls the production of the faster reaction, happens under milder conditions
primary alcohol oxidation (products)
aldehyde --> later carboxylic acid
a
The chemical reagent used to test for the presence of proteins is:
a) biuret
b) benedict's
c) iodine
d) sudan III
signal
messangers in cells are this type of protien
acidic hydrolysis is
opposite of esterification (acid and alcohol)
Removal of Water
Peptioc Bond is O to OH
first
the double or triple bond is numbered as the __ carbon involved in the bond
straight-chain alkane
an alkane whose carbon atoms are connected without branching
allotrope
a molecular form of an element. oxygen has two allotropes: O2 (diatomic oxygen) and O3 (ozone).
Structural Isomer
a molecule with the same molecular formula but different structural formula.
Nucleophilicity Trends
1. Increases as the (-) charge increases.
2. Increases down a group.
3. Increases to the left of a period.
Aryl: Salicylic Acid
.........CooH p
........... \ | /-OH o

/ | \
Transition state
Highest energy structure in steps of a reaction
order of stability of alkyl radical
tertiary> secondary> primary> methyl
excitability
the ability of the cell to respond to an electrical impulse
ketones
similar to an aldehyde in that it also contains a carbonyl group (C=O), but in a ketone, the carbon in the carbonyl group is not connected to any hydrogen atoms; C3H6O:propanone
more alkyl groups
Alkenes are more stable if they have...
functions of carbs
source of energy, short term energy storage, and support and structure in plant cells (cellulose) and animals (chitin)
Addition reaction
- Occurs when two reactants combine to form a single product
- Characteristic of unsaturated compounds
Thermal Reactions
Reactions that result by virtue of the kinetic energy put into a reaction vessel due to temperature
aldehydes vs. carboxylic acids
Aldehydes are easier to reduce because they only have two resonance structures, whereas carboxylic acids have three. This gives the aldehyde carbonyl a partial positive charge at least 50% of the time. the carboxylic acid carbonyl only has a partial positive charge 33% of the time.
increases rapidly
as the number of carbon atoms in a molecular formula increases, the number of possible isomers ________
unsaturated fat
one pair of carbon atoms are joined by a double or triple covalent bond of the fatty acid that makes up the fat (ex: olive oil)
alcohol boiling point compared to smiilar hydrocarbons
higher due to hydrogen bonding
IR spectroscopy polar bonds
More polar bonds yield more intense IR readings
What is a carbon branch of an alkane called
an alkyl group
What is the normal bonding pattern for the oxygen anion?
1 bond.3 lone pairs.-1 charge.
Bond dissociation enthalpy (BDE, also known as the bond dissociation energy)
The amount of energy released when pairing atoms...this same amount of energy would need to be absorbed to break the bond
Ka for HA + H2O <-> H3O+ + A-
Ka = [H3O+][A-] / [HA]
How do you draw the best Lewis Structure?
1) Octet Rule rules !
2) Do not place formal charges of the same sign on adjacent atoms
3) Minimize total number of formal charges
4) Avoid multiple formal charges on a single atom
5) Place negative formal charges on the more electronegative atom
6) Place positive formal charges on the more electropositive atom
ether
eth
2
cycloalkane
cyclo-
Alcohol
R-O-H
dec
ten
allyl
-CH2CH=CH2
RNA
ribonucleic acid
phenyl halide
prop-
3 carbons
Condensed Formulas
90
naturally occuring elements
succinic acid
butanedioic acid
sp3; four bonds
Tetrahedral
kinetic energy
energy of motion
alcoholysis
acid halide to ester
electrophile
In electrophilic aromatic substitution, this replaces a hydrogen in the original molecule
epoxide + H3O+
anti-additino diols
reduction of ketone gives...
secondary alcohol
R-NH2
The General Formula of Amines
polymers
large compound formed from combinations of many monomers
periods
horizontal rows of periodic table
Nitrogen containing Amides
RCONH2, RCONHR, RCONR2
DNA
deoxyribonucleic acid, contains the information needed by all cells
carbanion
A negatively charged carbon atom
Dehydrohalogenation
Loss of HX from alkyl halide
epoxides
3 membered cyclic ethers, more reactive than typical ethers, react with water in the presence of an acid catalyst to form diols
Cholestrol
molecules have a steroid structure made up of multiple rings;
Chitin
A structural polysaccharide of an amino sugar found in many fungi and in the exoskeletons of all arthropods.
maltose, lactose, sucrose
Disaccharides: example molecules: ________, ________, _______.
Primary Alcohol
Attached to 1 R Group
meta
A substituent of a disubstituted benzene that is two down from the primary substituent
doublet
A proton with one neighboring, nonequivalent proton gives a signal that is split into a double peak.
Organic Molecule
A molecule that contains carbon
R
From the Latin, rectus, straight, correct; used in the R,S convention to show that the order of priority of groups on a chiral center is clockwise
nucleic acid
polymers of nucleotides with specific functions in cells
Primary Structure
The level of protein structure referring to the specific sequence of amino acids.
glycogen
molecule that releases a form of energy that cans be used directly by cells
Fatty Acids
Molecules that contain a hydrocarbon chain and ends with an acid group
Nucleotide Coenzymes
transport hydrogen atoms and electrons (NAD+ and FAD)
Mass spec
molecular weight, presence of halogen, parent peak
pi-bond
sigma bond with additional pi bond between atoms, no room for other e- orbitals between the atoms, double bond, if another pi bond occurs, the atoms are triple bonded. weaker bond than sigma bond (less energy needed to break), overall the atom bond is strengthened and shortened. more reactive than sigma bonds
Oxidation of alcohol group
reaction produces acid(-uronic) glucuronic acid.
Amines
Have a carbon bonded to a nitrogen.
replication
how DNA makes a copy of itself
Functional group
an assemblage of atoms commonly attached to the carbon skeletons of organic molecules and usually involved in chemical reactions.
Constitutional Isomers
Compounds with the same molecular formula but a different connectivity of their atoms.
lipids
oils and fats that are insoluble in water
Secondary Structure
The second level of protein structure; the regular local patterns of coils or folds of a polypeptide chain.
Chemical Bond
Force of attraction that holds two atoms together as a result of the rearrangements of valence electrons between them
4
The number of bonds a single carbon atom can have
plasma
The liquid portion of blood is called blood _____.
Structural isomers
compounds that have the same molecular formula but different structures
carbohydrates
The main source of energy of living things. Composed of carbon, oxygen and hydrogen. Ratio of hydrogen to oxygen is 2:1
di
prefix for 2 branches of the same length
Monosaccharide
a simple sugar that is the basic subunit of a carbohydrate, single sugar molecule
Wolff-Kishner reduction
reduce a ketone or aldehyde by removing oxygen and replacing with two hydrogens
3,4-dimethylhexane
What is the name of the following compound?
diagram
Lanthanide
Any of a series of naturally occurring metallic elements between lanthanum 57 and lutetium 71 eg. Terbium Tb, 65
condensed structural formula
leaves out some bonds and/or atoms from the structural formula
antibonding MO
a molecular orbital that is higher in energy than the atomic orbitals from which it is formed
carbon skeleton
the longest chain of carbon to carbon linkages
isomer
one of two or more compounds that have the same chemical composition but different structures
Iron (lll) chloride
Lewis acid catalyst - used in chlorination of benzene
Saturated Hydrocarbon
All the carbon atoms are joined by single covalent bonds to other carbon or hydrocarbon atoms.
Racemic Mixture
A mixture of equal amounts of two enantiomers
dipole moment
occurs when the center of a positive charge on a molecule or bond does not coincide with the center of a negative charge
Covalent Bonding
A bond between 2 or more atoms sharing electrons. This bond is very strong
Determining the degree of unsaturation of a triglyceride
Alkenes undergo addition reactions with bromine water. Fats and oils which contain unsaturated groups will undergo the same type of addition reaction.
The degree of unsaturation can be determined by measuring the volume of a bromine solution required to react with a solution of a fat or oil in a cyclohexane. A solution of bromine in cyclohexane is added from a burette to a known volume of a fat or oil. The end point is indicated by first permanent colour change, the greater the amount of bromine which reacts, the greater the degree of unsaturation.
polarizability and basicity and how they are related
strong bases are slightly polarizable
preparation of a nitrile from a primary amide
Dehydration. Either SOCl2 or POCl3
Reduction of Amides
LAH > 1/2° amine; DIBAL > imine > aldehyde (after w/u).
carboxylic acid to alcohol
1. LiAlH4 2. H3O+ or 1. BH3 2. H3O+
The smaller the aldehyde the more unpleasant the odor, the larger the aldehyde, the more pleasant the odor
Distinguish between the smell of a small aldehyde and a large aldehyde.
When looking at a list of words, how could you easily pick out those that are sugars?
by looking for an -ose ending
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Term:
Definition:
Definition:

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