Organic Chemistry Flashcards

Terms Definitions
Chriality
Handedness
1
meth
-yne
alkyne
Dec
10
Propane
C3H8
ketones
1680-1750
alkene
-ene
esters
-C(=O)-O-, -oate
Alkenes
Double bonds
Nitrile
R-C(triple bond)N
=CO carbonyl
Keytone
Lipids
fats and oils
ester
sweet, fruity odors
acetone
nail polish remover
Synthesis of alkenes
Elimination
Dehydration
Dehydrohalogenation
example CnH2n+2
Type formula example
monosaccharides
simplest sugars(1)
ex. fructose, glucose
Tertiary Alkyl Free Radical
stable carbocation _____ Sn1
hastens
CnH2n
formula for alkenes (unsaturated hydrocarbons)
carbohydrates
store and release energy quickly
characteristics
functional groups affect the _________of organic molecules.
Sorbitol
alcohol found in sugar-free candies.
Atomic Number: 11
Atomic Weight: 22.99
Valence e-: 1
Na
carboxylic acids
Oxidation of aldehydes forms...
Radical Initiation
Heat/light-induced homeolytic cleavage (non-spont.) forms R from R2.
A Lewis acid
accepts an electron pair.
DNA
double stranded nucleic acid that stores and transmits genetic information
Protein
Monomers: amino acids, type, number and arrangement determines the protein, held together by Peptide bonds. Composition: C,H,O,N,S,Fe and others. Structure:cell members, muscles, enzymes
Polymerization
-composed of many repeating units (monomers) -dehydration-->remove water -addition-->join monomers by opening double or triple bonds and connecting molecules
Saturated
Hydrocarbons that have all single bonds
dehydration synthesis
bonds smaller molecules (monomers) together by removing H2O
diastereomer
Stereoisomers that are not mirror images of one another. some configurations are opposite.
carbohydrate
an essential structural component of living cells and source of energy for animals
Furanose
Five-membered ring formed by pentose or hexose sugars.
denaturation
enzymes are susceptible to this in globular proteins
base
compound that releases OH- ions in solution; pH greater than 7
but
prefix for a chain of 4 carbons
Single and Double sugars are called
simple sugars
phospholipid
a main component of the cell membrane
secondary structure
hydrogen bonding between amino acids cause the polypeptide to form an alpha helix or a pleated sheet; fibrous proteins
branched
__ hydrocarbons are named as the derivatives of straight-chain compounds in which one or more H atoms are replaced by hydrocarbon fragments
carbocation intermediates
Faster dehydration reactions have more stable...
bending vibrations
observed in lower frequency regions 1500-400
Linear
A bonding arrangement in which an atoms is bonded to other atoms in a straight line
Hydrocarbon
A compound that contains only carbon and hydrogen.
RNA
single stranded nucleic acid used for protein synthesis
Di-CooH
Glutoric Acid
(Pentanedioic Acid)
HooC-(CH₂)₃-CooH
Also can be:
α-Ketoglutaric Acid
HooC-Co-CH₂CH₂-CooH
Glutamic (GLU)
HooC-CNH₂-CH₂CH₂-CooH
5 or 6
Rings usually have how many carbons?
Functional Group
an atom within the organic molecules that determines the characteristic chemical properties of the particular family of organic compunds.
fatty acid
unbranched carbon chains that make up most lipids
primary structure
structure of protein: order of amino acids
aromatic hydrocarbons
a hydrocarbon ring containing 6 carbon atoms with 3 single covalent bonds and 3 double covalent bonds
Esterification
-organic acid + alcohol yields ester + water -dehydration synthesi
Reversible Competitive
Places the inhibitor on the active site; blocked by inhibitor.
E=hv
the energy of a photon is directly proportional to the frequency (more waves per unit time mean higher energy)
Hydrogen bonding
Peptide links are polar, and hydrogen bonding can occur both within a protein chain and between protein chains.
Bond Strengths
Hydrogen Bonds > dipole-dipole > van der Waal's
Dehydration Reaction
Chemical reaction where 2 monomers are joined by the removal of water molecules
MOLECULAR MULTIPLICATION
Halides
A chemical compound in which one of the elements is a halogen.
torsional strain
the strain in a molecule caused by electron repulsion between eclipsed bonds
Hydrolisis
When a water molecule is added to a polymer and breaks the bond.
Synthesis of Carboxylic Acids
From: Primary Alcohols Reagent: Basic KMnO4
carbon chain with an oxygen double bonded to the end carbon
structure of aldehyde
Nuclear Magnetic Resonance
based on how certain nuclei have magnetic moments that are oriented at random and when they are placed in a magnetic feild they aligh with or against the direction of applied force
organic halide
organic compound in which one or more hydrogen atoms has been replaced by a halogen atom (also known as a halocarbon)
PCC (Pyridinium Chlorochromate)
Oxidize 1° alcohol to aldehyde w/o gem-diol.
Mass Number
The number of protons plus the number of neutrons
nitrogen base, pentose (sugar), and phosphate group
3 parts of a nucleotide
low polarity, cannot H-bond
Alkanes are hydrophobic for these two reasons
Cis Isomer
an isomer of an alkene in which the hydrogen atoms in the double bond are on the same side
Free Radical Addition of HBR to Alkenes
HBR
------>
ROOR/hv

Adds H and Br
Anti-Markovnikov
no rearrangements
relative nucleophilicities in aprotic solvents
F⁻ > Cl⁻ > Br⁻ > I⁻
how to separate enantiomers?
allow a racemic mixture to react with a single enantiomer of some other compound. This changes a racemic form into a mixture of diastereomers, and diastereomers, because they have diff. melting pts, boiling pts, and solubilities, can be separated by conventional means. enzymes also work - they'll only react with one enantiomer, & change it into something else.
wins the electron battle
if something is left of carbon in the periodic table
rules for resonance structures
1) atoms not to be moved 2) # of unpaired e- is constant 3) resonance atoms must lie in the same plane 4) only proper lewis structure is allowed
meth, eth, prop, but, pent, hex, hept, oct, non, dec
prefixes for chains having 1 to 10 carbon atoms
Phenol
(0)-OH
8
oct
alcohols
-OH
R-OH
Hex
6
Hexane
C6H14
R2C=CH2
890
cycloalkane
cyclo-
Pineapple
Ethyl butanoate
Acid Halide
O=C-X
-COOH Carboxyl
Acid
Soaps
contain ester groups
-oic acid
carboxylic acid
Hydroboration-Oxidation of Alkenes
1.)B2H6
------------>
2.)H2O2/NaOH

Adds H and OH
Anti-Markovnikov
syn addition
positivee
charge of the nucleus
2 classes of hydrocarbons
-aromatic
-aliphatic
Molecular structure of isobutane.
para on benzene
across from
CnH2n+2
formula for alkanes (saturated carbons)
electrons
negative particles of an atom
negative
phosphate is ____ (the charge)
quinine
Malaria Medication
-found in tree bark.
Atomic Number: 19
Atomic Weight: 39.10
Valence e-: 1
K
HCN
The formula for hydrogen cyanide
Common Valences
C=4, N=3, O=2, H=1.
nitro
nitrogen double bonded to oxygen bonded to a carbon single bonded to another oxygen
Hydrocarbons
compound composed of carbon and hydrogen
starch
a polymer of a simple sugar
Organic
Study of the compounds of carbon
cofactor
many enzymes need require nonprotein helpers for catalytic activity
unsaturated
less than four single bonds(contains double or triple bond)
polymer
a naturally occurring or synthetic compound consisting of large molecules made up of a linked series of repeated simple monomers
Gibbs Energy
ΔG = ΔH - TΔS.
phospholipid bilayers
the hydrophobic and hydrophilic ends stay away
organic compound
compound that contains carbon bonded to hydrogen and is found in living things
hept
prefix for a chain of 7 carbons
hydrocracking
catalytic cracking in the presence of hydrogen to give mixtures of alkanes
polysaccharide
several single sugars that are joined together (complex carbohydrate)
alkyl groups
hydrocarbon fragments that are derived from the alkanes by removal of a hydrogen are called __ __
oxidation
A reaction with increased oxygen or decreased hydrogen
spin-spin coupling
Protons that split each other's signals
Nonbonding electrons
Valence electrons not involved in forming covalent bonds. Also, called unshared pairs or lone pairs
Other Ester Reactions
1. conversion to Amides (Direct)
RCo0CH₃ + H₂N-R--> FCoNHR + CH₃OH
2 Rxn Grignards
2G + Ester --> 3° Alc (2 R Groups same)
∅-MgBr + RCo0CH₃ --> [[RC(OMgBr)(∅)0CH₃]] --⁻CH₃OMgBr--> RCo∅ --∅MgBr/H₂O--> RC(OH)∅₂ (Stable)
Carbon
Element made up of atoms with four valence electrons. Can also bond to other carbon atoms.
Configurational Stereoisomers
Have the same molecular formula and same atom to atom bonding sequence, but the orientation of atoms/groups in space differs.
activation energy
minimum amount of energy required to start a chemical reaction
triglyceride
lipid composed of glycerol and 3 fatty acids
saturated hydrocarbons
all bonds between carbon atoms are single covalent bonds
Amine
-nitrogen on end of carbon chain -name ends in "amine"
Reversible Noncompetative
Places the inhibitor on some other site other than the active site; enzyme is effected by something else.
Carboxylic acid
a compound contating a carboxyl group (-COOH)
Acid hydrolysis of amides
Products: carboxylic acid and protonated amine
RCONH2 + H3O+ ------> RCOOH + NH4+
RCONR'R + H3O+ ------> RCOOH + RCONH-R'-R
Alkyl Group
R
Fragment of a molecule derived from an alkane by removing a hydrogen atom.
Carbon Analogy
Jess and his cool toys
Companionship for toys
Structual Formula
A chemical formula showing the linkage of atoms in a molecule diagrammatically.
inductive effect
pull of e- density through sigma bonds caused by electronegativity differences of atoms
Carboxyl Group
Double bond between C and O. Attatched to the C is another O atom. Then to that is a H. Hydrophillic.
polar covalent
The hydrogen and oxygen atoms in a single water molecule are held together by a type of bond called a _____ ______ bond.
Two names for the polymer used for cookware, valves and bearings, plumbing, lubrication
teflon (polytetrafluoroethylene)
Carboxylic ester
a derivative of a carboxylic acid in which H of teh carboxyl group is replaced by a carbon
Anti-Markovnikov Hydration of Alkenes
Hydroboration: BH3 + alkene + oxidative workup (NaOH) > least-substituted alcohol.
Homologous Series
Belonging to or being a series of compounds where each successive member of which differs from the preceding member by a constant increment, especially by an added CH2 group.
Ribose and deoxyribose
have 5 carbon backbones, and are the building blocks for nucleic acids
geometric isomer
a compound that exists in two or more geometrically different configurations
Branched Chain
an open chain of atoms with one or more side chains attached to it
Substitutive Method for naming Alcohols
base=longest chain w/ OH
OH gets lowest possible #
name ends in "ol" ("anol")
precede name w/ OH locant # (unless number is 1)

DOES NOT INCLUDE HYDROXY
Sn2 vs. E2 (1° substrate)
if base is strong, elimination is favored (steric hindrance)
Homolytic fission
The bond is split in half - each side takes 1 electrons and 2 free radicals are formed
they are not going to react
if one molecule is dissolved in solution and the other is not,
index of hydrogen deficiency
# of pairs of H a compound requires in order to be a saturated alkane. IHD = 0.5 * [2c+2-h-x+n]
How is the boiling points of alkanes compared
more carbons in the chain results in higher boiling points
12
dodec
-oate
ester
Prop
3
Ethane
C2H6
amines
R-NH2
aldehyde
-al
Nitro group
NO2
hydrogen sulfite
bisulfite
=O, -NH2
amide
Element
Simplest pure substance
halogenation
reaction adding halogens
benzoic acid
benzoic acid
Benzylic Halogenation
X2 (X=Cl,Br)
---------->
NCS,NBS/hv

Adds X to benzylic carbocation
25
elements essential to life
sugars and starches
sugars-simple
starches-complex
Carboxylic acid chloride
-oyl chloride
oxidation/reduction: loss of X2
reduction
dipeptide
Two amino acids bonded together
Waxes
Sticky, solid, waterproof lipid consisting of many long-chain fatty acids usually linked to long-chain alcohols
carbon: hydrogen: oxygen
the 1:2:1 ratio
Galactose
-Brain sugar
-Part of lactose-milk sugar
Constitutional isomers
same formula, different connectivity
Ethers
Carbon chain interrupted by oxygen;
Recrystallization
Purification via diff. solubilities; filtration separates crystallized precipitate from supernatant.
Shielded
Surrounded by electrons whose induced magnetic field opposes the externally applied magnetic field. The effective magnetic field at the shielded nucleus is less than the applied magnetic field.
Alkanes
straight or branched hydrocarbons with only single covalent bonds, name ends in ane
achohols
ends in ol/always have an OH
Branched and non-branching
Types of structural isomers
org + o2 = co2 +h2o
combustion
Hydrocarbon Families
carbon chains with hydrogen-carbon bonds (Alkanes, Alkenes, Alkynes)
cyclo
refers to a ring of carbon
Nucleic Acids
Macromolecules made up of hydrogen, oxygen, nitrogen, carbon, and phosphorus, used to store and transmit hereditary or genetic information (DNA and RNA).
hydrolysis
a water molecule is inserted, breaking a bond
substrate
reactant in a chemical reaction that happens in a living thing
eth
prefix for a chain of 2 carbons
kerosene
a thin, volatile oil distilled from petroleum, with a boiling range higher than that of gasoline and lower than that of diesel fuel; kerosene was once used in lanterns and heaters, but now most of this petroleum fraction is further refined for use as jet fuel
proteins
organic polymers made of amino acids linked in a specific order
aromatic hydrocarbon
six-membered carbon ring that exhibits resonance
alkoxides
Conjugate bases of alcohols, which are weak acids
Octet rule
The tendency of main-group elements (Group 1A-7A) to achieve an outer shell of eight valence electrons
Enzyme
A protein that speeds up chemical reactions in living things.
glycogen
compound used by animals to store carbohydrates in the liver and skeletal muscles
Acid Chloride
Most Reactive
HCl is VERY corrosive
Always Unstable
-Must have a Hetero(more e-neg than C) Atom
Best Leaving group? R- or ∅- or {Cl-}
A. Can prep for all other acid derivatives
B. FC Acylation- source ROC⊕
C. RCOCl --LiAlH(o-t-Bu)₃/selective Red'n--> RCO-H
D. Organo Metallics selectivity to give Ketones
-R₂Cu⁻Li⁺ or R₂Cd
SP3
tetrahedral 109.5 .. ..
-o- or, -N-
.. ..
isotope
atoms of the same element that have different numbers of neutrons
tertiary structure
structure of protein: folding of one chain
carbon, oxides, carbonates
Organic chemistry refers to the... containing compounds, that exclude... (2)
Properties of Organic Compounds
-soluble in nonaqueous solvents -nonpolar -nonelectrolytes (except organic acids) -low melting points (covalent bonds) -slow reactions
Lipid Bilayer
Is a two-layer thick structure of phospholipids and glycolipids in which the nonpolar tails of the lipids are in the middle and the polar heads are on the outside surfaces.
amino acid
molecule containing both an amino and a carboxyl group
glass transition temperature
temperature at which polymer turns flexible
Condensation
To produce an amide, the amine group from one amino acid is able to undergo condensation with a carboxyl group from another amino acid. What's produced is called a dipeptide. The amide group that forms is a peptide link:
O H
| | |
C - N
What are characteristic peaks of ethers? (IR)
C-O (1000-1250) only!
Aldose
Sugar where carbonyl group is at the END OF CARBON CHAIN
Allotropes
The name given to pure elements that can exist in more than one structural form eg. O2 oxygen gas, O3 ozone gas
rearrangement reaction
a general reaction type in which a molecule undergoes bond reorganization to yeild an isomer
split-second hydrogen bond
In liquid water, molecules form a '______________' _____ ______ even though each may be moving in a different direction.
The polymer used for plumbing, floor tiles, shoe
soles, shower curtains, and artificial leather
polyvinyl chloride (PVC)
Carboxylic amide
a derivative of a carboxylic acid in which the -OH is replaced by an amine
IR spectra for C=O
a sharp dip around 1700 cm⁻¹
Grignard Addition of CO2
R-MgBr + CO2 > carbox. acid.
Atomic Number
The number of protons plus the number of electrons
Triglycerides (Neutral fats)
formed by the attachment of 1-3 fatty acids to a glycerol; rich source of energy, having 2x(+) the energy per weight as carbs
substitution reaction
a reaction in which one or more atoms replace another atom or group of atoms in a molecule
Halogenation (X and OH) of Alkenes
X2 (X=Cl,Br)
----->
H2O

Adds X and OH
anti addition,OH on more stable
no rearrangements
effect of substrate in Sn1 rxns
halide should be 3° ((relative stability of carbocation formed))
When two amino acids are joined what do they form
A dipeptide and water
Polyunsaturated Fatty Acid
Is a fatty acid with a carbon chain in which two or more carbon-carbon double bonds are present.
Name all the Electron Donating Groups in order
NH₂, NHR, NHR₂, OH, OR, Alkyl, NHCOR, I, Cl, Br, F
how do you tell the difference between carbohydrates and lipids if they are made of the same atoms?
there are less carbon atoms in lipids than carbs
Acetylene
Ethyne=IUPAC
Butane
C4H10
alcohol
ol
alkyne
-C≡C-
=O, -O-
ester
(-)-DET O
Up
hex-
6 carbons
acyl group
R-C=O-
monosaccharide
single sugar molecule
monounsaturated
1 double bond
conformers
a conformational isomer
bronsted-Lowry acid;
proton donor
Alkene Halogenation (products)
dihalogenated alkane
disulfide reduction (H) =
thiols
non-
carbon prefix for 9
oxy
oxygen between two carbons
rings
Carbon can form chains and...
addition
Hydrogenation is an _____ reaction
branched-chain
carbons left-not a continuous chain
halogens add to alkene _____
anti
Hexose
a monosaccharide that contains six carbon atoms per molecule
allyl group
the univalent unsaturated organic radical C3H5
Rule #3
List groups alphabetically (Not including prefixes)
circulation
continuous movement around from one place to another
HVZ reaction
carboxylic acid to alpha halogenation
greater electron charge
+--> arrow points to
nucleophile
Substance with free pairs of electrons
Solution
A homogenous mixture that contains particles the size of a typical ion or small molecule
Steriods
flat molecules made of four interlocking hydrocarbon rings (example: cholesterol)
Cis

Trans
Both on same side of molecule

Different sides of molecule
How many bond can carbon form?
Four bonds
hydrogen atoms
hydrogen atoms must make one bond
Cn H2n+1
the type formula (general molecular formula) for Alkyls
how many total amino acids are there?
20
organic chemistry
studies millions of compounds which are always made up of carbon and hydrogen and sometimes include oxygen, nitrogen and sulfur
Synthesis of Primary Alcohols
From: Esters Reagent: LiAlH4
Propyl Group
CH3 - CH2 - CH2 -
eclipsed conformation
the geometric arrangement around a carbon-caron single bond in which the bonds to substituents on one carbon are parallel to the bond to substituents on the neighboring carbon as viewed in a Newman projection
extraction
"based upon solubility due to similar polarities, of like dissolves like"
ether
Which one of the following compounds does not contain a carbonyl group?
Meat, poultry, and whole-milk dairy products are high in what type of fat?
Saturated fats
syn- addition
same side addition of hydrogens during hydrogenation
Atomic Structure
Simpliest form of an element that retains the properties of that element is called an element.
Three major parts:
Protons- Postivley charged particle-Located in the nucleus
Neutron- no charge
Electron-negativley charged particle-no mass-located outside nuclues
atom
The smallest unit of matter that has the characteristics of an element
Radical stability
Increases as number of R groups increases
rate constant
the proportionality constant kr in the rate equation
isomerism
the possession by two or more distinct compounds of the same molecular fromula, but in different arrangement.
heterocyclic
ring shaped carbon chain which has to have at least one atom that isn't carbon in the ring
CH3Ch2O-
---------->
ethanol
bonds to C and ADDS ethoxide as leaving group solvates
What is the name of this functional group?
Aldehyde.
Fatty Acids
simple forms of fat that supply energy fuel for most of the body's cells
Peptide
the kind of bond formed when two amino acid units are jointed end to end
Free Radical Substitution
Uses ultra violet light. Alkane + halogen gas > haloalkane. Reaction occurs through homolytic fission to form a free radical
a (alpha) helix
right handed coil that is threaded like a standard wood screw (helix)
Neutralisation of carboxylic acids
They are neutralised by hydroxide ions, carbonate ions, and hydrogen carbonate ions forming a carboxylate salt.
Hydroxide ions:
RCOOH + OH- ------> RCOO- + H2O
Carbonate ions:
RCOOH + CO3 2- -------> 2RCOO- + H2O + CO2
Hydrogen carbonate ions:
RCOOH + HCO3- --------> RCOO- + H2O + CO2
Mercaptan
A common name for a thiol; that is, any compound that contains an -SH (sulfhydryl) group (This literally means mercury capturing, these react with Hg2+ in aqueous solution to give sulfide salts as insoluble precipitates.)
A Chiral Center
Can be superimposed on its mirror image, does not rotate plane of polarized light.
glycerol and fatty acids
The building blocks of lipids are: _________________________ & __________________________.
What are some polysaccharides used for structural molecules?
Cellulose, Chitin, and Peptidoglycan.
Secondary (2°) amine
An amine in which nitrogen is bonded to two carbons and one hydrogen
TRANS fat
Fake fat, body is confused and puts in in artery in the heart
Saturated fatty acid
A fatty acid in which all carbons in the hydrocarbon tail are connected by single bonds, thus maximizing the number of hydrogen atoms that can attach to the carbon skeleton.
Polar solvent
A solvent is a polar solvent if it has a dielectric constant of 15 or greater
CO₂ + H₂O --> C₆H₁₂O₆ + O₂
Write the chemical equation for photosynthesis.
Name four ways that enzymes can be deactivated.
1. incorrect pH
2. incorrect temperature
3. heavy metal contamination
4. competitive inhibitors
If a bond is stretched, what occurs?
A restoring force pulls the two atoms together toward their equilibrium bond length.
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Term:
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