O-Chem Deck Flashcards
Haloform; CH3, methyl ketone
*I2, excess, OH- is the … reaction. It removes a … from a …
dextrorotatory; levorotatory; S
+ Rotation = …; - Rotation = … If you have an R enantiomer, it’s mirror image will be …
Carbonyl, an Alcohol
… appears around 1720 cm^-1, … gives a broad signal around 3300 cm^-1
Tollens; acid
1) Ag2O, NH3 2) H3O+ is the … reagent. It will oxidize an aldehyde into an …
aniline (NH2)
1) Sn, HCl, 2) OH- react with a Nitro (NO2) group on a benzene ring and make
Zwitterion, Amino Acids
A … is a molecule that has both a positive and negative electrical charge on different atoms within the molecule. They are commonly found in …
*Alkyl and Allylic Halides= Positive in AgNO3 in alcohol *A precipitate of AgX is formed
A chemical lab test using AgNO3 in alcohol is used to test for … and … A precipitate of … is formed.
*Chromate oxidations= Primary and Secondary alcohols are oxidized. *Reddish-orange dichromate gives a greenish solution, same as Jones oxidation.
A chemical lab test using Chromate oxidations is done with … The reddish-orange dichromate or chromate agent shows a … solution. … oxidation gives the same result.
70% R + 30% R+S (racemic) = 85% R, 15% S
A compound is 70% pure R, the it’s entire composition is …
Polarimeter
A device used to measure the effect of plane-polarized light on optically active compounds is called a
Double bond or ring contributes: 1 degree of unsaturation Triple Bond contributes: 2 degrees of unsaturation
A double bond or ring contributes … degrees of unsaturation, a triple bond contributes … degrees.
a primary amine
A Gabriel Synthesis is a simple SN2 mechanism in which a primary alkyl halide is converted into …
*Alkenes, alkynes and alcohols dissolve when added to cold H2SO4 *Alkanes and alkyl halides are insoluble
A lab test with concentrated H2SO4 dissolves … Other substances such as … are insoluble.
optical activity, chiral carbons, a plane of symmetry
A meso compound has no …, it does however contain … and …
greatest
A molecule that is branched and possesses symmetry can fit into a crystal best, thus has the … melting point.
highest, greatest, greatest, lowest
A molecule with no branching will have the … boiling point, … amount of surface area, … amount of dispersion forces and the … melting point.
2200 cm^-1
A Nitrile, CN (triple) bond would give an IR band at
mutarotate, negative, negative, NO hemiacetal group
A Non-Reducing sugar will not …, give a … Tollens test, a … Benedicts test and will not contain a … group.
Zwitterion
A nuetral form of an amino acid such that it is equally protonated and equally deprotonated is called a
Amino group, Carboxy group
A peptide bond or amide bond is formed between the … of one amino acid and the … of another amino acid.
Tollens (+)= aldehyde; alpha-hydroxy ketone 2,4 DNP (+)= carbonyl group
A positive Tollen’s test suggests either … or … A positive test with 2,4-DNP suggests a … group.
polypeptide subunits.
A proteins quaternary structure is the arrangement of …
the 3-D shape, Fibrous proteins; collagen sheets/long strands
A proteins tertiary structure is …, examples include …
centrifugation, the bottom
A red blood cell in plasma is best separated by … in which the more dense particles settle towards …
*Ag(NH3)2OH= this is a test for alkynes with terminal triple bonds
A silver nitrate in ammonia Ag(NH3)2OH chemical lab test was performed to test for …
raise
A soluble nonvolatile substance such as NaCl will … the boiling point.
*Tollens Test- primarily for Aldehydes, uses Ag(NH3)2 or Ag2O/ NH3 *The reaction flask is coated with a “mirror of silver” Remember **Positive Tollens Test also means a reducing sugar, that will mutarotate, and give a positive Benedicts Test
A Tollens test is primarily a test for … using … For a positive result, the walls of the reaction flask are coated with a “…
high
Alcohols have hydrogen bonding which increases the intermolecular forces of attraction which gives rise to a … boiling point.
an Amino group, a Carboxyl group, and a variable R-group side chain
All amino acids contain (3 things)
deactivate
All meta directors … the ring
not be, protonation by acqeuous acid, ammonium salt.
Amines larger than 3 carbons will … water soluble. Amines become soluble by …, which converts the Amine into a water soluble …
Amide
An acyl halide reacts with a primary amine to yield?
an Anhydride.
An acyl halide reacts with an acid (COOH) to form …
an alpha hydrogen, remove, the alpha hydrogen, an enolate anion
An Aldol Condensation reaction can only occur if the aldehyde or simple ketone involved contains … because we must … the …in order to generate ….
1650 cm^-1
An alkene would give an IR band at
2200 cm^-1
An alkyne would give an IR band at
1700 cm^-1
An anhydride would give a pair of bands around
1200 cm^-1
An ether would give an IR band at
separation, isolation
An extraction with solvents is used for … and … of substances from mixtures.
*Iodoform Test I2/OH-: Positive for a methyl ketone, or methyl carbinol. *A yellow precipitate of CH3I (iodoform) forms
An Iodoform I2/OH- chemical lab test was used to test for … A … precipitate of … formed.
Fatty Acid; fatty acids contain long hydrocarbon chains and a single acid group C14H28O2= CH3(CH2)12COOH
An unknown compound was identified as C14H28O2. This compound is likely a:
cyclic, planar sp2 hybridization/ p-orbitals Huckel’s Rule: 4n + 2 pi electrons.
Aromatic compounds must be …, planar, with every atom of the ring having …, while obeying Huckel’s Rule of …
unreactive
Aryl halides (aromatic) and vinyl halides (double bonds) are … in both SN1 and SN2 reactions.
1-4 addition, thermodynamic
At high temperatures a conjugated diene will give the major product as …, this is under … control.
1-2 addition, kinetic
At low temperatures a conjugated diene will give the major product as …, this is under … control.
negative, it doesn’t contain a true double bond, but rather a resonance hybrid.
Benzene gives a … test in Br2/CCl4 and cold dilute KMnO4 because …
double or triple bonds; colorless, brown
Br2/CCl4 and cold, dilute KMnO4 react with compounds containing … For this test orange/brown Br2/CCl4 becomes … and purple KMnO4 turns …
lowers, surface area
Branching … the boiling point of a molecule because branched molecules have less …
3300 and 3400 cm^-1 due to the two H’s attached to the N.
CH3CH2NH2 will contain two weak absorbtions at approximately … and … due to the …
Epoxidation occurs
CH3COOOH reagent indicates that …
Baeyer-Villiger reaction, an ester
CH3COOOH reagent indicates the … reaction. An aldehyde or ketone is converted into …
oxidize, acids
Compounds such as Ag(NH3)2+ (tollens reagent) or Ag2O are mild agents used to … aldehydes into …
axial, equatorial
Consider (trans)-1-bromo-3-methylcyclohexane. The most stable conformation is given when bromine is … and methyl is …
Column chromatography and Crystallization can be used to seperate two isomers. First a mixture is dissolved in ethanol and cooled, the para isomer will crystallize out, and the ortho isomer will not. Crystals are then isolated and the mother liquor is run through a column to purify the ortho isomer.
Consider p - Nitroaniline and o - Nitroaniline. What methods are used to seperate these two compounds?
tautomers
Constitutional isomers that co-exist in rapid equilibrium are called
syn-same face; also it adds in the direction that creates the least steric hindrance.
D2 , like H2 simply adds across a double bond in a … fashion.
random coil
Denaturation causes a protein to lose its structure and revert to …
Epimers
Diastereomers in which two molecules differ in configuration about one carbon are called
water, 5 or 6 membered ring. See #235 if unclear, Destroyer 2011
Dicarboxylic acids can readily lose … when heated if they can form a …
different, different
Different bonds vibrate at … frequencies, thus they absorb … frequencies of IR light.
2’, deoxyribonucleic acid, outside the helix, interact with water.
DNA lacks a … OH group, it is a … acid. The sugar and phosphate groups lie … where they are able to …
*Alkenes and Alkynes = Positive in dilute KMnO4 *Deep Purple KMnO4 turns brown
During a chemical lab test using dilute KMnO4 … give a positive test and cause deep purple KMnO4 to turn …
*Alkenes, alkynes = Positive test in Br2/CCl4 *The orange brown color decolorizes
During a chemical lab test with Br2/CCl4 … give a positive test, in which the orange/brown color of Br2/CCl4 …
last, first
During column chromatography the order of elution depends on the polarity of the molecule. The most polar molecules elute … and the least polar molecules elute …
Wittig= (:P(Ph)3+ with an alkyl group) Ph= phenyl/ benzene ring
During the … reaction we synthesize an ylide.
FeBr3
During the Bromination of Benzene, which catalyst is employed?
*trans: highest priority substituents are opposite *cis: highest priority substituents are on same side
E means … Z means ..
Carbocation intermediate, Rate Law; 1st order k[halide], both are favored by tertiary substrates, since tertiary halides form tertiary carbocations
E1 and SN1 both share (3 properties)
increase, decrease; strongly acidic
EWG’s … acidity, ERG’s … acidity. A ring with an ERG and an EWG para to one another is …