Organic final Flashcards

Terms Definitions
Flouro
F
-OH
alcohol
pent-
5
eth
2
Methane
CH₄
hept
7
cycloalkane saturation
saturated
aldehyde HNMR
8-10
carbonyl group
C=O
But-
4 carbons
-C=-N:
sp 180 linear
double bond CNMR
100-140
Alkane
CnH2n+2, saturated, sp3
8 carbon atoms
octane
Alkenes are______ to 1,2-diols
oxidized
maturation
Transformation from unspecialized function to specialized
Catabolism
Metabolic breaking down process.
∆Hº is positive
endothermic rxn
http://classconnection.s3.amazonaws.com/1498/flashcards/714083/jpg/halogenation.jpg
Halogenation/BrominationCl2/Br2 can be added to alkene such that each alkene carbon gets one halogen. Exhibit anti-sterochemistry (each halogen gets added to the opposite faces of the alkene kinda like trans)
Ether
C - O - C
fructose
"Fruit sugar;" is a monosaccharide
covelant bond
the sharing of electrons
The polymer used for fabrics
polyester
carbonyl 13C NMR chemical shift
180-215
examples of williamson ether synthesis
polymerisation
through addition reaction, alkene molecules can be
\ /
C=C
/ \
sp2 trigonal planar 120
Eth-
the prefix meaning 2 carbon atoms
denaturation
the unravelling of polypeptides which causes them to loose their shape and function
What makes something inorganic?
doesn't contain carbon
simplest carboxylic acid
methanoic or formic acid
what is methanol known as
wood alcohol
Alkanes
Saturated Carbon Chain; Fuels; Prefix + "ane"
imine
amine double bonded to alpha carbon
Amide
Synthesis via reaciton of acid chlorides with amines or acid anhydrides with ammonia. Suffix-amide
Alkene
ending = ene, double bond + single
trans
the isomer in which the substituents are on opposite sides of the double bond or ring
22
How many atoms of hydrogen in C₁₂H₂₂O₁₁?
Carbohydrates
compound made up of carbon, hydrogen, and oxygen atoms (its a ring); major source of energy for the human body, the monomers are Monosacharide and Complex Carbohydrates
The bottom
Hotter part of a distillation tower
ester reduction into aldehyde
1. DIBAI-H 2. H3O+
aromatic hydrocarbons
Hydrocarbons that contain a ring structure similar to benzene
conformer
one of the infinite number of rotations
alkyl group
the partial structure that remains when a hydrogen atom is removed from an alkane
ethylene glycol
dacron and mylar are produced from
alcohols
a hydrocarbon derivative with at least one hydrogen replaced by hydroxyl (OH⁻)
NaNH2, NH3
---------->
H2O
REMOVES geminal or vicinal halides:
haloALKANES ----> ALKYNES
Fractional Distillation
Sep. azeotropes/small diff. in bp; more SA for condensing/revolatizing vapors.
Ethers
Oxygen links two parts of hydrocarbon chain
Methoxymethane=dimethyl ether
resonance forms
the only difference is the placement of the (pi) and nonbonding valence electrons.
symmetrical bond formation
one e- donated by each reactant
Glutaraldehyde
though a mild preservative and a good disinfectant, is known to be harsh on rubber tubing
IUPAC names
the systematic names that follow the rules adopted by the International Union of Pure and Applied Chemistry
hydroxyl group
hydrogen atom bonded to oxygen atom that is bonded to carbon skeleton
acetoacetic ester synthesis
production of a ketone from acetoacetic ester due to the strongly acidic properties of the alpha hydrogen
hydrophobic
A substance that is not soluble in aqueous solutions is said to be...
Primary
Carbon (1°) is bonded to one other carbon.
glucose
is blood sugar. energy source for most cells
infrared spectroscopy
polar bonds within a compound stretch and vibrate
Dextrorotatory
Refers to a substance that rotates the plane of polarized light to the right
Reagents of organometallics with alpha and beta-unsaturated carbonyls?
1-2?
3-4?
 
R-MgBr
then H3O+
 
R2CuLi
the H3O+
Aldol Addition
the enolate ion of an aldehyde or ketone reacts with the carbonyl carbon of a second molecule of aldehyde or ketone, form a B-hydroxyaldehyde or a B-hydroxyketone. The new C-C bond forms between the alpha-carbon of one molecule and the carbon that formerly was the carbonyl carbon of the other molecule
how many bonds does carbon have
always has 4 bonds
kinetic order
the power of a concentration term in the rate equation
what makes up a nucleotide?
sugar(deoxyribose), a phosphate group, and a nitrogenous base
Vitalism was what?
the belief that only living organisms could make organic compounds
area under peak in nmr
proportional to number of hydrogens
Gauche Conformation
A conformation about a single bond of an alkane in which two groups on adjacent carbons lie at a dihedral angle of 60 degrees.
Electronegativity
a measure of the ability of an atom in a chemical compound to attract electrons
aldehyde carbonyl
a double bonded oxygen at the end of the carbon chain
Lewis dot structure
the symbol of an element surrounded by an number of dots equal to the number of electrons in teh valence shell of the atom
anti addition
A reaction in which the two groups of a reagent X-Y add on opposite faces of a carbon-carbon bond
functions of nucleic acids
1. dictate the amino acid sequence
2. stored info that determines genetic characteristics
2. specificity determined by the fact that only certain bases bond with each other
ex: A-T and C-G
amide, amine, ester, carboxylic acid, ketone, aldehyde, thiol, ether, alcohol, haloalkane, aromatic, alkyne, alkene, alkane
order of class (highest to lowest)
if the allylic radicals have resonance, which radical gives the major product?
the most stable radical gives the major product
What is the formula for true selectivity?
% of product/# of H positions
a --> B+ C ; ENtropy is changing how
increasing, more molecules more randomness due to clamming
Nonane
C9H20
pka
-logKa
electrons
negatively charged
Cred (creddible)
believe
superior/inferior
up and down
Carboxylic acid anhydride
RCOOCOR
trigonal planar bond angle
120
Cataclysm
n. a violent change
transpiration
water evaporates into plants
______________ acids have large acidity constant (Ka) values.
Strong
enantiomers
nonsuperimposable mirror images of each other; always come in pairs (if a molecule has an enantiomer, then it must be chiral)
lipids
organic compounds that are waxy/oils
Do alkanes have low density?
Yes
Graded expiration
support phrase length, intonation, pitch, loudness
diastereomers
stereoisomers that are not mirror images of each other
Conformational isomers
Molecules that have different arrangements.
organic
grown or prepared with natural fertilizers or without the use of insecticides and other chemicals
myxobacterium
reproduce by budding not binary fission
Soap: Saponifaction
Triglycerides are hydrolised by Sodium Hydroxide to form Sodium Salt of the Fatty Acid and Glycerol
Frontal Lobe
motor planning and execution, speech production, grammar, executive functions
low density lipoproteins
carry cholesterol to peripheral tissues and help regulate cholesterol levels in those tissues.
Hydrocarbons
Those that only contain the elements Carbon and Hydrogen
Classes of hydrocarbons
alkanes, alkenes, alkynes, and arenes
aldehyde or ketone
What does EAS acylation make?
Classical theory componets
1)A system of differentinated activities
2)People
3)Cooperation toward a goal
4)Authority
What is the formula for any carbohydrate?
Cn(H2O)n
careen
v. to sway or lurch sideways, esp while moving rapidly
splitting of peaks is caused by ?
neighboring H's
stereo-selectivity of Diels-Alder Rxn
syn-endo isomer; anti- exo isomer
Functional Groups
The most reactive part of the molecule, also used to identify the type of organic compound
dipeptide
2 amino acids formed by a peptide bond
Stereoisomers/structural isomers
differ in arrangement of atoms in space.
anhydride group
Two carbons each connected to R groups as well as carbonyls, connected together via an oxygen
geminal dihalide
carbon with two halogens bonded to it
Structural formula
shows which atoms are bonded to which (lewis structures)
Saytzeff's rule
When more than one b-carbon has H atoms, the most substituted C undergoes elimination
Carbocation stability and structure
Carbocations are planar. The trivalent carbon is sp2-hybridized, all three substituents are oriented to the corners of an equilateral triangle. The p orbital extending above and below the plane is unoccupied. Stability of + charge on a carbon increases with increasing substitution. The more alkyl groups that are attached to a positively charged carbon, the more electron density shifts toward the charge and the more inductive stabilization of the cation occurs. Methyl < Primary<Secondary<Tertiary. If there is a more stable carbocation waiting next door, there will undergo a hydride or alkyl group shift to yeild the more stable carbocation.
hydrogen bond
hydrogen atom has covalent bond w/ 1 electronegative atom; ex. water
anhydride group
Two carbons each connected to R groups as well as carbonyls, connected together via an oxygen
Why is that?
The dimer form allows the carboxylic acid to solvate without disrupting the hydrogen bonds of the dimer, allowing it do dissolve without breaking the hydrogen bonds.
Alkene with NBS in aqueous DMSO
Same as X-X addition:
Anti addition
bridge as intermediate step
no rearrangements
X+ adds to less substituted C
How can bonds break
symmetrical: one electron ends up with each product fragment. Called homolytic. Ex: radical. Unsymmetrical: Both bonding electrons end up with product fragment, leaving the other with a vacant orbital. Called heterolytic.
What does this do to the conjugate base?
It stabilizes it
Do amines with comparable molecular weights have higher or lower boiling points than alkanes?
They have higher boiling points.
OsO4, t-BuOOH or KMnO4, H2O, NaOH
reagent for reaction that produces double alcohol from alkene
Orientation of electrophilic addition: Markovnikov's rule
In the addtion reactions a single product is given from an unsymetrically substituted alkene...not a mixture of products. This reaction is regiospecific. So Markovnikov's rule: In the addition of HX to an alkene, the H attaches to the carbon with the fewer alkyl substituents and the X attaches to the carbon with more alkyl substituents. If both Carbons are equally substituted then there will be a mixture. If there is an intermediate carbocation in the reaction the more susbstituted carbocation is formed as the intermediate rather than the less highly substituted one.
What do aldehydes and ketones react with alcohols to form?
They form hemiacetals and hemiketals.
What is a zwitterion?
A zwitterion is a molecule that has a positive and a negative charge somewhere in the molecule, yet is neutral overall.
So what actually happens?
You take an alkene and you turn it into an alkane
Are beta-lactams reactive or unreactive?
They are higly reactive due to large ring strain.
Determine sp hybridization of atom
the sum of single bonds and lone pairs equals 2
What happens during this reaction is peroxide (ROOR) is present?
Bromine will add to the least substituted carbon
So overall, what happens in the pinacol rearrangement?
You're taking a vinical diol, dropping a hydroxyl group, moving a methyl group to that spot, and forming a carbonyl on the other hydroxyl group.
Is a base a weaker or stronger nucleophile than its conjugate acid?
It is always a stronger nucleophile than its conjugate acid.
What happens when hot sulfuric acid is added to an alcohol?
The expected product of dehydration is an alkene.
Is the leaving group going to be stronger or weaker than the nucleophile?
It will always be mor estable than the nucleophile
What happens if you add R-X to NR2H2?
You add another R group to it, producing R3N
What happens if you add Br2 or Cl2 to an alkene?
They add via anti-addition to form vicinal dihalides
6
Hex-
Amine
R3C-NR2:
cis-trans-isomers
geometric isomers
geminal halide formation
2HX
aryl group
aromatic cyclohexane
reagents accompanying BH3
H2O2, -OH
Olefin
Any unsaturated aliphatic hydrocarbon.
Weak activating ortho para
-R -Ar
prepare an ether
RX + -OR
t-alkyl groups
make a sideways T
Ortho,para
Which directing group takes precedence?
What are moderately withdrawing electron groups?
peak area?
number of H's in peak
Minion
n. an employee, hireling, or subordinate
nucleic acid
large complex organic molecules composed of carbon, oxygen, hydrogen, nitrogen, and phosphorous atoms
temperature
measure of heat intensity; represents average kinetic energy of molecule, regardless of volume
What does glucose become?
It becomes glucopyranose.
Lewis acid
species available to accept electron pairs to form new bonds
cleavage of terminal alkyne creates?
carboxylic acid, CO2
elimination
functional group removed and pi bond is formed
nucelotides
built from special 5 carbon sugar, phosphate group, nitrogenous base
element
substance can't be broken down to other substances thru chemical rxns
Sagittal
A lengthwise plane running from front to back dividing the body or any of its parts into right and left sides
Carboxylic Acids: Esterfication
Reacting with Alcohols, gently heating with concentrated Sulfuric Acid to form and Ester and Water
The cerebrovascular system
supplies the brain with blood (oxygen)
2nd degree alcohol with CrO3
2nd degree = Ketone
if the ends contain methyl groups and the very end has H, it will be
iso-something
Hydroxylation
The two step process of taking an alkene and turning it into an epoxide, then using an acid catayst to perform hydrolysis is called hydroxylation. The hydrolysis used with acid gives a trans glycol product. The use of OsO4 in pyridine with an alkene, followed by NaHSO3 in water will skip the intermediate epoxide and result in a cis addition glycol.
covalent
carbon forms this type of bond with oxygen, nitrogen, phosphorus and sulfur atoms
Proximal
Toward or nearest the trunk of the body or the point of origin of a particular part
What is this reactiona sometimes called?
A hoffman rearrangement.
functional speech impairment
the cause of difficulties with speech development cannot be determined precisely; most phonological disorders or delays are functional
carboxyl group (-COOH)
a chemical group consisting of 1 carbon atom, 1 hydrogen atom & 2 oxygen atoms (-COOH)
Is combustion spontaneous?
No, it requires heat to occur, usually via a flame.
Whats so special about water?
It's a good leaving group.
formal charge
the amount of charge it has in a molecule or an ion
(group number) - (nonbonding electrons) - (0.5)(shared electrons)
Chiral Probe
A molecule that is chiral and can use its own chirality to differentiate between mirror imagines
amino
nitrogen atom bonded to 2 H atoms & to a carbon skeleton
What do these properties affect?
They affect a protein's tertiary structure.
great plains dust bowl
1) poor soil practices 2) took away grasses with long roots 3) new plants with short roots 4) soil erosion happened
What are polar protic solvents?
They are solvents that can hydrogen bond.
What is the pinacol rearrangement?
It is a dehydration of an alcohol.
carbonyl group--> gets rid of O and adds H
What does Zn(Hg), HCL do?
Is this the end of our halo-radicals?
No! This reaction can continue indefinately, or it can go through the third and final step of halogenation.
Explain the key diffe rences between SN1 and SN2. For each, give an unambiguous example and draw a reaction coordinate energy diagram
In SN1, a two-step process occurs involv ing loss f the leaving group to form a carbocation intermediate, followed by reaction of the nucleophile with the cation, resulting in the formation of a racemic mixture. This happens when the carbocation is highly substituted, the leav ing group is good, and the solvent can stabilize the cationic intermediate. A good substrate example is tert-butyl bromide. In SN2 a single-step process occurs involving simultaneous attack of the nudeophile and loss of the leaving group, resulting in complete inversion of the configuration of the electrophilic carbon center. This happens when the electrophilic carbon center is less substituted, when the leaving group is not as strong, and the solvent cannot support the formation of ions. A good substrate example is methyl chloride.
Do they form strong or weak bonds with ions?
They form strong bonds with ions
What happens when the hydroxyl group is protonated?
The good leaving group, water, is formed and substitution results.
What is the carbon at the opposite end of the chain called?
It is called the omega carbon.
What does this infer about acidity values of alkenes versus alkanes?
Alkenes are more acidic as a result of the willingness to gain electrons
What makes a Ketone + Aldehyde from an alkene?
1) O3 2) Zn, H2O or
1) O3 2) CH3SCH3
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Term:
Definition:
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