Organic Chem Flashcards

Terms Definitions
-anol
R-OH
1kcal
4.184kJ
ch3-ch-ch3-ch2-ch-oh-ch3
4-metil-2-pentanol
NH2
amino
Ester
-anoate
Propyl
3 Carbon
thesis
to put
BH3:THF
H2O2/OH-/H2O
 
Regiochem/Stereochem/Rearrangements Possible
Regiochem/Stereochem/Rearrangements Possible
 
Anti-Markovnikov/Syn Only/No
Base
More OH ions
categories of carbohydrates
monosaccharidesdisaccharidespolysaccharides
non polar
hydrocarbon, benze ring
Eicosanoids example
prostaglandin-regulates blood clotting, inflammation and labor contractions
Animals (sources of proteins)
egg white
(multiple identical functional groups) 3 groups
tri-
carbocation
positively charged carbon intermediate that forms as a result of heterolysis (electrophile)
Difference between 1s and 2s is
energy
Distillation
Process that can separate two substances in a mixture by evaporating a liquid and recondensing its vapor.
polymers
large molecules formed by joining together many smaller molecules called monomers
geometric isomers
same linkages, different arangements in space. (have to see them)
Hund's rule
 
fill parallel before filling one
condensation reaction
a reaction between two smaller molecules to form a larger molecule
Aromatic Compounds
have alternating single and double bonds throughout the structure
2
Reaction of R-M with carboxylic acid derivatives. Acid clorides and esters can be converted to ketones or 3 prime alcohols with organometallic reagents. The indentity of the product depends on the identity of R"-M and the leaving group Z=Cl.
esters
Characterized by the presence of the following
C double bonded to an O C single Bonded to an O
Hg(OAc)2, H2O + NaBH4
Markovnikov addition without rearrangement
ester reactions
hydrolysis (saponification) by acid or base, conversion to amide (NH3 displaces), transesterification (exhange of alcohols), Grignard addition (forms tertiary alcohol through ketone intermediate), Claisen condensation to beta-keto ester, hydrolysis by LAH to 2 alcohols (CO and OR bond split)
chromatography
A TECHNIQUE THAT IS USED TO SEPARATE THE COMPONENTS OF A MIXTURE BASED ON THE TENDENCY OF EACH COMPONENT TO TRAVEL OR BE DRAWN ACROSS THE SURFACE OF ANOTHER MATERIAL
what are lipids good for
energy storage, hormones, vitamins
alcohol
an organic compound in which an -OH group is bonded to a saturated carbon atom.
hemiacetal
the family of org compounds formd via rxn of 1 molecule of alcohol w/ an aldehyde in the presence of acid catalyst (STRUCTURE)
increases
The BE _____ with increasing number of bonds
At equilibrium, the ____ acid and the ____ base are the major species found in the reaction mixture
weaker
Atomic Number
The number of protons in an atom's nucleus
Properties of Alkanes
nonpolar bonds. held together by weak London Dispersion Forces. state of matter depends on molecular mass.low-gas. natural gas-1 to 4 carbons. boiling point depends on the molecular mass. Low mass low boiling point
Dopamine is created only in the....
anywhere in the body
Free Radical
a highly reactive species due to an unpaired electron that resulted from the homolytic bond cleavage (breaking)
Enzyme action
1. Enzyme's active site binds with substrate2. Enzyme & substrate rearrange to form product3. Enzyme releases product
Pinacol rearrangement
When adding acid to a vicinal diol, we will do a methyl shift, being able to form a double bond, and then deprotanate with water.
3D shape and form
is critical because things have to fit.
Specific Heat
The amount of energy need to raise the temperature of 1 gram of water by 1 degree Celsius
nitro compound to aniline compound
addition of zinc and dilute HCl
Horizontal lines represents bonds pointing towards you. Vertical lines represent bonds pointing away from you.
What do the lines in Fischer projection represent?
sec and iso butyl
sec is when methyl is on carbon connected to main chain and iso is when it is one further away
Order of reactivity in SN2 from least to most
Tertiary, Secondary, Primary, and Methyl
Hydrogen bonding of alchs does what to bp and solubility?
increase bp and increases solubility in water!
What happens when you mix an alcohol with an anhydride? (p. 481)
ROH + R-Acid anhydride-R --> R-Ester-R + R-Carbox
conjugated
anti-bonded
Ammonia
NH3
Pent
5
Cl
chloro
Ketone
-anone
Amine
Contain N
philic
to love
Imine formation
not high ph
COO-
aniline to nitrobenzene
CF3--(=O)--O--OH
C-13
1.1% of all Carbon
Deprotonate -NH3?
spider N thing
Alcohols Description
•nomenclature
◦Prefix: hydroxyl, hydroxy.
◦Suffix: -ol, alcohol.
•physical properties
◦Hydrogen bonding.
◦Higher boiling point than the same compound without the alcohol group.
◦Water soluble as long as molecule does not contain a long hydrophobic region.
•infrared absorption of OH group: 3300 cm-1 and broad due to hydrogen bonding.
Do alcohols have hydrogen bonding?
yes
Products
ending substances in a reaction
hydrocarbons
compounds that have hydrogen and carbon
N2
NH2 + NO = ? (aromatic)
antioxidant
a substance that protects other substances from being oxidized bu oxidizing itself in preference tot he other substances.
ketones
Contain the carbonyl functional group within the carbon chain
parent peak
molecular ion-corresponding to the unfragmented cation radical
 
shows the mass spectrum of propane
chiral carbon
allows the occurence of optical isomerism because of the four different groups surrounding it
NH, OH, C=O, C=N
What are grignard's limitations?
Sublimation
solid is purified by vaporizing and condensing it without going through an intermediate liquid phase. Solid must have an unusually high vapor pressure.
polymer
A long Chain-like molecule made of repeating units or monomers.
poly- = many
-mer = parts
radical
a reactive intermediate with a single unpaired electron (electrophile)
BH3 or B2H6
Antimarkovnikov hydro bromination, syn addition
NaBH4 reduces what compounds?
Carbonyl Groups (C=O)

Aldehydes --> primary alcohol
Ketones --> secondary alcohol
Chiral molecule
A molecue that is not superimposable upon its mirror image. In order for a molecule to be chiral it must at least one chiral center
C-11
And existing isotope of Carbon but is not naturally occurring
monohalogendos, polihalogendos
los derivados de los halogendos se deviden en
aromatic hydrocarbon
a hydrocarbon containing one or more benzene rings
what is a cycloalkane?
hydrocarbons in a closed ring
Ionic Bonding consists of ?
electrostatic attractions between ions of opposite charge
Things that need lipids
hibernating animals (bears, frogs) , migrating animals (geese), seeds (peanut, sunflower)
Primary Structure
The sequence of amino acids in a protein. This sequence dictates the final shape of the protein because electrochemical bonding and repulsion forces act on the structure to create the folded-up protein
Dopamine plays a role in...
(e) all of the above
structural formula
a formula that is drawn out/ shows unshared electrons
acylation to amine
NH3 and cat H+ then LiAlH4
In ethane, carbon with three hydrogens is bonded to
carbon with three hydrogens.
Thioester
have a -SCH3 bonded to the C=O (like a O in Ester, S in thioester)
homolysis (homolytic cleavage)
the breaking of a bond and equally dividing the electrons between the two atoms
Hoffmann rearrangement
addition of BrO- to amide, Br adds to nitrogen, proton is removed from nitrogen to form a negatively charged nitrogen, R group attacks nitrogen while lone pairs attack CO carbon and Br acts as leaving group (nitrene is negatively charged nitrogen, isocynate is back-to-back O,C,N double bonds with N bound to R
Alkyl Radical & Hydrocarbon Radical
What are 2 Other Terms for Radicals:
sugar stereochemistry
losest OH on left is L and right is D
non bonding molecular orbital
an orbital that is formed if the two new orbital from overlapping have different signs (this forms a node) (zero electron density/ high energy/ unstable) *
What is a functional group?
The atoms or groups of atoms of an organic molecule that undergo predictable chemical reactions.
what does the term outer shell of Nitrogen refer to?
it means how many electrons are available to bond or be a LP
ie tripple bonded N -C, Nhas 8 e-
- 6 bonding 2- nonbonding
Isopropyl
Heptane
C7H16
Prop
3
ketal
(structure)
6
hex
simmons-smith product
cyclopropane
organic compound
...
ether
C-O-C (dimethyl ether)
grain alcohol
ethyl alcohol
meta
1 C in between
Methyl trichloride
chloroform (or) trichloro-methane
triphenylphosphine (PPh3)
making wittig reagents
TMS
alcohol + (CH3)3SiCl in Pyridine
finger print region(IR)
1500 to 400
IUPAC
Systematic method to name alkanes
Sn1
tertiary halogenoalkanes react in this method; first the halogen breaks off then the nucleophile attaches onto the positively charged carbon
wood alcohol, Methanol, methyl alcohol
aka carbinol
Hydrohalogenations
the addition of a hydrogen halide
Osmium tetroxide (OsO4)
Dihydroxylation of alkenes (1,2-diols)
Isomer
same Number and kind of atoms, different arrangement
Organic Compounds
Contain carbon except carbonates and oxides
A reaction in which stereoisomeric products are formed in unequal amounts (from a starting material) with one being given predominance.
Stereoselective reaction
Nitration
the substitution of a nitro group (NO2) for a hydrogen on benzene (H2SO4)
monosaccharides examples
pentose (5 carbon) deoxyribose, found in DNAhexose (6 carbon) glucose-blood sugar galactose fructose
carboxylic acid
contains a terminal O=C-OH group CH3, O=C-OH (acetic acid) (-ic acid)
Aliphatic - alkanes ◦physical properties
■Hydrophobic.
■London Dispersion Forces present only.
■Lower boiling points than compounds the same size but with functional groups.
■Very long alkanes can have very high boiling points due to the sum of all the dispersion forces. A useful reference is that heptane, the 7 membered alkane, has the same boiling point as water.
transition state
the highest energy point in a reaction
ane
What is the Suffix that Indicates a Saturated Hydrocarbon?
Pi bonds
bonds formed by the sideways overlap of p orbitals
ketone/aldehyde reduction
sodium borohydride and acid (both form alcohols)
Grignard reagent
An alkyl magnesium halide used to make carbon-carbon bonds. Alkyl group in a Grignard reagent has a negative charge and acts as a nucleophile attacking electrophilic carbons.
conformational isomers
a form of stereoisomerism in which the isomers can be interconverted by rotations about formally single bonds
branched hydrocarbons
HCs with side groups on the longest c-chain
dipole moment
A measure of the charge separation in a molecule
Carbox Dissociation
SHOULD BE DRAWN WITH AN EQUILIBRUIM SIGN
◦ring strain in cyclic compounds
■Cyclopropane has the highest ring strain.
■Cyclobutane has the second highest ring strain.
■Cyclohexane has the lowest ring strain.
■Any ring with greater or equal to 14 carbon atoms has the next lowest ring strain.
Functional Group
What is Defined as a group or singular Element Attached to a Carbon Compound that Adds Certain Characteristics to that Carbon Compound?
spectator ions
Ions that do not bind until the very end of the reaction
NH2NH2, OH- or Zn(Hg), HCl does what?
removes double bond oxygen
Rxn as a Base with Organometallic reagents
organometallic reagents are strong bases that readily abstract a proton from water to form hydrocarbons CH3-Li base +H-OH to CH3-H +Li+ OH-
Claisen Condensation is....
The formation of a Beta - Keto ester and Alcohol from two esters and alkoxide bases

NaOR/H30
The Chemistry of Flavor and Fragrance Perspective (3)
Carboxylic Acids Smell Very Bad. Butryic Acid is the smell of gangrene and rancid butter. Esters however smell good as Ethyl Butyrate is the smell of pineapples.Although fruits have a complex mixture of esters so the flavor is never fully embodied, scientists make fruit based artificial flavors made of esters that taste and smell good. One such example is Methyl butanoate (CH3CH2CH2esterCH3) which is the main ester responsible for the taste of apples.
Change all but anomeric on cyclic
Do acid and EtOHthen add NaOH, MEIORDo NaOH and MEI on all, anomeric is not stable in acid like this, so add acid and water, and anomeric will go back to OH
How do you determine the type of hybrid orbital formed by an atom?
Count the number of sigma bonds and lone pairs, then match that to the sum of the superscript in the hybrid name (sp, sp², sp³).
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Term:
Definition:
Definition:

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