organic chemistry review Flashcards

Terms Definitions
H-CI3
Iodoform
aldehyde
R-C(=O)H
-one
ketone
H₂C=CH₂
Ethylene
Alcohol
R-OH
ester ending
-oate
benzyl group
C6H5-CH2-
protein
natural polypeptides
Circular Shape
Cyclo-
Hydration Rxn-general rxn
(alkenes)
...
ethers in rxn
non-reactive
3
N valence e-'s
alkane general formula
CnH(₂n+₂)
Ketone
Organic carbon/hydrogen compounds containing a double bonded O not at an end
methine group
the CH group
toluene
benzene with 1 methyl
Carboxylic Acid
C O OH
sp3d2; five bonds
Square Pyramidal
primary alcohol oxidation (catalyst/agent)
[O], K2Cr2O7
Trigylcerides
3 fatty acids and glycerol
-yne
at least 1 triple bond
-anoic acid
suffix for carboxylic acid
nitrile
hydrocarbon with a C-triple bond-N
amino acids
building blocks of proteins
Radical Halogenation of Alkanes
X2 (X=Br,Cl)
------->
heat/light

RH----->RX
involves radicals
double helix
chains run in opposite directions
polymerization
process by which polymers are formed
alkanes
a hydrocarbon containing only single covalent bonds
LiAlH4
Amides and Nitriles are reduced by...
spectrum
chart of peaks showing the relationship between frequency and absorbed energy
hydrocarbon cracking
increases the proportion of hydrocarbons at the expense of higher-molecular-weight ones by cleavage of carbon-carbon bonds, Either thermal or catalytic
lactose
galactosidic linkage of galactose and glucose
Aryl: Phthalic Acid
.................CooH (para)
..............\ | /-CooH (ortho)

/ | \
Z configuration
Highest priority groups on same side
endergonic
A chemical reaction that requires the input of energy in order to proceed.
A pentagon cyclic ether (4C-1O) is called
furan
Proteins
Nutrients that help build and maintain body tissues
When alkanols reacts with a carboxylic acid what comes first when naming?
alkanol
Reduction of epoxide reagents
1. LiAlH4 2. H2O
Hydrocarbons that only contain single bonds
saturated hydrocarbons
trans
a geometric isomer which has like groups on opposite sides of the double bond
ethylene C2H4
molecule that polymerizes to form polyethylene
Cis-trans
Alkenes that have the same connection between atoms but differ in their 3-D structures because of the way that groups attach to different sides of double bond
Sucrose
produced by sugar cane. fructose and glucose. known as table sugar. ex: cookies
Aliphatics
Compounds which do not contain a benzene ring; may be saturated or unsaturated (alkanes, alkenes)
Ozonolysis
cleaves double bond and forms double bond to Oxygen
http://www.khanacademy.org/video/naming-alkenes-examples?playlist=Organic%20Chemistry
 
naming clyclo enes**
when solving cyclos first point of double bond is usually assumed to be one (no identification needed)
if there is a subst directly bonded to double bond then THAT is one
must move across double bond like a bridge no matter what
amine
sp3 carbon bound to sp3 nitrogen (when hooked to one N its primary amine, 2 N is secondary amine, etc)
exothermic
describes a reaction in which a system releases energy to its surroundings
-yne or -ylene
The common ending of those hydrocarbons that contain at least one trivalent bond
Waxes
formed by attachment of long chain of fatty acids to long-chain alcohols or carbon rings (serve as coats for animals and plants to keep things in and out)
inorganic compounds
compounds that DO NOT contain carbon and hydrogen
NaBH4, LiAlH4
Reducing Agents for C=O (ketones and aldehydes)
Geometric figures are used to show the structure of what hydrocarbon family
Cycloalkanes
Alkenes
____ are carbon chains with a double bond.
Brønsted acid
a substance that can donate/lose a proton
What is the name of this compound:
CH3-CH=CH2 ?
1-Propene
anti markovnikov
hydroboration least sub carbon adds OH across double bond BH3/O2H2
Determining Resonance
1. filled valence shells
 
2. max # of covalent bonds
 
3. least separation of unlike charge (double bond)
 
4. negative charge on the more electronegative atom
retrosynthesis of grignard reagents
1. identify alcohol and alpha carbon
2. dreak off one of the substituents and add MgX to it
3. the rest of the compound becomes a carbonyl (replace the OH with a double-bonded O
( if you have two identical substituents you can use an ester and 2 equivalents of your grignard reagent)
polyunsaturated fat
at least two double bonds between the carbons (fat)
Amino group
A functional group that consists of a nitrogen atom bonded to two hydrogen atoms; can act as a base in solution, accepting a hydrogen ion and acquiring a charge of +1.
substituent
an atom or group of atoms that can take the place of an H atom on a parent HC molecule
phenyl, aryl
As a substituent, an aromatic ring is called either a ___ or a ___ group
Electron pushing
Keeping track of electron pairs by a curved arrow (bookkeeping symbol)
Substitution
A reaction in which an atom or group of atoms in a compound is replaced by another atom or group of atoms.
Equatorial Bonds
A bond to a chair conformation of cyclohexane that extends from the ring roughly perpendicular to the imaginary axis through the center of the ring: a bond that lies roughly along the equator of the ring.
Mechanism of E1 Reaction
Slow step: X- leaves, forming a carbocation
Fast step: the base removes a proton from a beta-carbon, and a c=c is formed
cis-trans isomers (geometric isomers)
isomers that differ in their geometric arrangement on a ring or double bond; cis-trans isomers are a subclass of diastereomers
magnetically equivalent protons
Protons that are in the same magnetic enviroment in a molecule have the same chemical shift in an NMR spectrum
Cirtius rearrangement
Start with an acyl azide, use H2O and heat, last is decarboxylation. The migration of an -R group from the C=O carbon atom to the neighboring nitrogen atom with simultaneous loss of a leaving group.
Alkylation and acylation of the alpha carbon of aldehydes and ketones by means of an enamine intermediate
NH/trace H+ then RCH2Br/HCl,H2O, CH3CH3O=OCl/HCl, H2O, CH2=CHC=OCl, bind to the alpha carbon
Preferences for resonance structures
1- structures in which all atoms have filled valence shells (complete octets), 2- structures with a greater number of covalent bonds, 2- structures that involve the least separation of unlike charges, 4- structures that carry a negative charge on am ore electronegative atom and ones that carry a positive charge on a less electronegative atom
What is catabolism (catabolic reactions)?
Used to break down large molecules into smaller molecules (monomers) by the addition of one water molecule at each bonding side
if alcohol is used in oxymercuration instead of water
ether is formed instead of alcohol
D and L Glucose
If lowest OH is on the left, then it is an L-Glucose. If lowest OH is on the right, it is D Glucose. D-glucose is the most common in nature.
nitrile/cyano
CH2=CH-C:::N
meth
one
heptane
C7H16
formaldehyde
methanal
amonia
NH3
monosacchrides
simplest sugars
Carbonyl Group
C=O
SN2 reaction
aromatic hydrocarbons saturation
unsaturated
C _= C
2260-2100
coenzyme
an organic cofactor
phenol
bezene with alcohol
lipoproteins
transport lipids through bloodstream
benzene
6 carbon aromatic hydrocarbon
Functional Group containing C-O-C
Ether
Separation (Lab Techniques)
-distillation-(Boiling point)
-chromatography-(Polarity)
-extraction-(Solubility)
polysaccharide
polymers of monosaccharides that sometimes store energy
rasidual(R)
the portion of formulation representing any hydrocarbon.
carboxylic acids (-oic acids)
-COOH... O=C-OH
Alkene
CnH2n, unsaturated, sp2, double bonded
secondary alcohol oxidation rxn =
ketone
negative charge and polarizability ________ nucleophilicity
increase
saturated fat
single bond between a carbon
Alkene hydrogenation (catalyst/agent)
Ni, Pd, or Pt
alkane
a hydrocarbon having only single bonds; a saturated hydrocarbons; CnH2n+2
hydrolysis
last of five categories of reactions
Carbonyl
C=O, polar, Found in carbs, aldenhydes
strong conjugate acids
Good leaving groups have...
alkyl
aliphatic compound called this and represented by R
isomers
molecules with the same chemical formula but different structural formulas
DNA
double stranded nucleic acid that stores and transmits genetic information
carbocation
trivalent carbon with a positive formal charge
Spin-spin splitting
(magnetic coupling) The interaction of the magnetic fields of two or more nuclei, usually through the bonds connecting them. Spin-spin splitting converts a single signal to a multiplet, a set of smaller peaks.
functional groups:
they are the chemically functional part of the molecule, and are the non-hydrocarbon part
Methyl salicylate
Another name for Oil of wintergreen
ester
an organic compound made by chemically combining an alcohol and an organic acid
Amines
Description: An amine (NH2) bonded to a carbon atom.
Naming: -amine
Polypeptide
Large number amino acids linked by peptide bonds
NMR
they must have different energy states that we induce
unsaturated fat
have double bonds, originate in plants, are liquid at room temperature
Hydrocarbons
made from chains of carbon and hydrogen
eclipsed conformation
a conformation about a carbon-carbon single bond in which teh atoms or groups on one carbon are as close as possible to atoms or groups on an adjacent carbon
aldehyde protons on nmr ppm
"9.5, far downfield"
Terpene
A compound whose carbon skeleton can be divided into two or more units identical with the carbon skeleton of isoprene
Racemic mixtures
equal mix of stereoisomers

do not rotate plane polarized light
Enolate ions of B-diketones, B-diesters, B-keto esters, and B-keto nitriles undergo
Michael Reactions with alpha,beta-unsaturated carbonyl compounds. This kind of reactions form 1,5-dicarbonyl compounds
MO theory
an alternate theory to valence theory. the molecular orbital is consedered as atomic orbitals applied to the bonds between two atoms.
di
prefix for 2 branches of the same length
enzyme
A protein serving as a catalyst, a chemical agent that changes the rate of a reaction without being consumed by the reaction.
direction
glucose found in starch has the same formula as glucose in cellulite except the differentiating factor is that the _________ of the molecules are switched
Aromatic Hydrocarbons
compounds that have a pleasant aroma Ex) wintergreen, cinnamon, vanillin
radical reaction
homolytic or -genic ond formation and breaking
Ring current
under the influence of an external magnetic field, these pi electrons circulate around the ring
Curved arrow
A symbol used to show the redistribution of valence electrons in resonance contributing structures or reaction mechanisms, symbolizing movement of two electrons
Benzylic carbocation
A carbocation in which a carbon attached to a benzene ring bears the positive charge
Enamine Formation
2° amine + carbonyl > enamine (N-carbonyl C=β carbon).
Endothermic
H+, bonds in the products are weaker les stable, than the bonds in the reactions, heat is absorbed, and the reactions endo thermic
series of hydrocarbons
alkane: -ane 2n + 2
alkene: -ene 2n
alkyne: -yne 2n - 2
how many bonds must a carbon make to be stable?
4
What allows us to get the energy from food?
enzymes
Introns
A segment of DNA that has no apparent genetic message for a gene.
antibonding MO
a molecular orbital that is higher in energy than the atomic orbitals from which it is formed
side group
a group of atoms replacing hydrogen on the longest chain of carbon atoms
What are characteristic peaks of nitriles? (IR)
C-=N (triple bond...) (2200-2250)
Organic Chemistry
Chemistry of C compounds. 95% of all compounds.
acidity of alcohol
can lose a proton, less acidic than water, strongest to weakest: methyl, primary, secondary, tertiary. most stable conjugate base is the conjugate of strongest acid
acyl
C is central with =O and R connected , one open connection
glycerol
a kid of alcohol that has 3 -OH or hydroxyl groups in its molecule
Dipole moment
A measure of the polarity of a bond (or a molecule), proportional to the product of the charge separation times the bond length.
lock and key model
enzymes are specific and only 1 will fit with a certain substrate
Lewis Definition of Acids and Bases
Acid electron pair acceptors, Base electron pair donors.
Hydration Rxn- properties
(alkenes)
- adds OH to more substituted C on Dbl bond
G double dagger defines what??how do you find it in a graph??
defines the RATE OF REACTION -->through the Ea Peak - the previous base connected to wave
What does the orbital represent in an atom?
represents the space where an electron spends most of its time
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Term:
Definition:
Definition:

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