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Definitions |
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(CH3)2-CH
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isopropyl
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(CH3)3-CH2-C
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neopentyl
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Pyranose
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Six-membered rings
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R(=O)-OH
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Carboxylic Acid
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Furanose
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five-membered rings
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DMSO
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Good Polar Aprotic Solvent.
Therefore, good in SN2 reactions.
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Aldose
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Glucose, Galactose, and Mannose
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Aromatic Rings
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Nitric (HNO3)/Sulfuric acids
(name product)
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Product: Nitro Compounds
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Ketal
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Functional group or molecule containing the functional group of a carbon bonded to two -OR groups.
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CH3MgBr + D2O --> ?
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DCH3
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KMnO4
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Oxidizing agent
Change toluene to COOH.
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Substituent Effects
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1. Activating, ORTHO/PARA-directing substituents: (electron donating) NH2, NR2, OH, NHCOR, OR, OCOR, R
2. Deactivating, ORTHO/PARA-directing subs (weakly electron withdrawing): F, Cl, Br, I
3. Deactivating, META-directing substituents (electron withdrawing): NO2, SO3H, Carbonyl compounds (COOH, COOR, COR, CHO)
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Claisen Condensation
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Important reaction of ESTERS.
Simplest case: two moles of ethyl acentate react under basic conditions to produce a beta-keto ester. Also called teh acetoacetic ester condensation.
Enolate ion of one ester acts as a nucleophile, attacking another ester.
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Parts of Forebrain
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Also called PROSENCEPHALON
Consists of:
Telencephalon and Diencephalon
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Dihybrid Cross
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Parents differ in TWO traits.
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Grignard reagent
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RMgX (equivalent to R- nucleophile)
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Isomers
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Chemical compounds that have same molecular formula, but differ in structure.
May be extremely similar or extremely different.
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Nondisjunction
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Either the failure of homologous chromosomes to separate properly during MEIOSIS I, or the failture of sister chromatids to separate properly during MEIOSIS II.
Can result in trisomy (2N +1) or Monosomy (2N -1).
e.g. trisomy is down syndrome (chr. 21)
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Purine
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Purine is a heterocyclic aromatic organic compound, consisting of a pyrimidine ring fused to an imidazole ring.
(4 nitrogens: 2 in hexane ring, 2 in pentane. They are attached)
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Sporophyte Generation
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DIPLOID sporophyte produces haploid spore by MEIOSIS.
Spores divide by mitosis to produce the haploid or gametophyte generation.
e.g. Ferns: Sporophyte is dominant.
Angiosperms: Woody plant seen is sporophyte stage.
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Antiaromatic
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A cyclic, conjugated polyene that possesses 4n electrons.
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Sulfonation of Aromatics
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An electrophilic aromatic substitution.
Aromatic reacts with fuming H2SO4 (mixture of SO3 and H2SO4) to form sulfonic acids.
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acetal
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Molecule with two single bonded oxygens attached to the same carbon atom.
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Sympathetic Nervous System
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"Flight or Fight"
Increases blood flow to skeletal muscels, and decreases gut motility.
Dilates bronchioles and uses NOREPINEPHRINE as primary neurotransmitter.
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Recrystallization
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Separates solids based on differential solubility; temperature is important here.
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Spectroscopy
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Process of measuring the energy differences between the possible states of a molecular system by determining the frequencies of electromagnetic radiation absorbed by the molecules.
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Carbohydrates
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Aldehydes and ketons with many hydroxyl groups
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Basic Amino Acids
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Arginine, Lysine, Histidine
Amino acids whose R-group contains an amino group and carry a net positive charge at physiological pH.
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Pyrmidine
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Pyrimidine is a heterocyclic aromatic organic compound similar to benzene and pyridine, containing two nitrogen atoms at positions 1 and 3 of the six-member ring.
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Which type of reaction causes inversion of chiral centers?
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SN2
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Which reaction prefers a protic solvent?
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SN1
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Polymerization
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Creation of long, MW chains composed of repeating subunits in alkenes.
Occurs through radical mechanism, requires HIGH TEMP and PRESSURE.
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Transesterification
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When a different alcohol attacks the ester, the ester is TRANSformed, and TRANSesterification results.
(ester into another ester)
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Huckel's Rule
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4n + 2 pi electrons
Important indicator of aromaticity.
n = any nonnegative integer; thus can be 2, 6, 10, 14, 18, etc.
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Peroxycarboxylic Acids
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Alkenes can be oxidized with peroxycarboxylic acids.
e.g. Peroxyacetic acid (CH3CO3H) OR m-chloroperoxybenzoic acid (mcpba).
Products = Epoxides or Oxiranes.
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Nonpolar Amino Acids
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Valine, Alanine, Isoleucine, Leucine, Proline, Phenylalanine, Glycine, and Tryptophan.
non - "TV PIG PAL"
Have R-groups that are saturated hydrocarbons. R-groups are hydrophobic and decrease solubility of amino acid.
Often found at core of globular proteins or in transmembrane regions of proteins.
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Monosaccharides
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Simplest units and are classified by the number of carbons.
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Oligodendrocytes
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Produce myelin in the central nervous system
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Racemic mixture
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Mixture of equal concentrations of both the (+) and (-) enantiomers.
Rotations cancel each other out, thus NO optical activity.
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Oxidation Addition
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Alkynes can be oxidatively cleaved with either basic KMnO4 followed by acidification or Ozone.
KMnO4 Product: 2 M COOH
Ozone Product: 2 M COOH
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Hybridization
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Concept of mixing atomic orbitals to form new hybrid orbitals.
Useful in explanation of shape of molecular orbitals.
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Auxins
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STIMULATE the production of NEW XYLEM cells.
Important class of plant hormones associated with several growth patterns:
1. Phototropism
- (growth towards light; Indole acetic acid is one of the auxins associated with phototropism) - MORE auxins = DECREASED growth.
2. Geotropism:
(Growth TOWARDS or AWAY from gravity)
- NEGATIVE geotropism = Causes shoot to grow UPWARD, AWAY from acceleration of gravity. (INCREASE in auxin = incerase growth)
- POSITIVE geotropism = Causes roots to grow TOWARDS the pull of gravity. (HIGH concentration of auxin = inhibit growth)
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Diastereomers
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Differ in chirality, but are NOT mirror images.
For any molecule with n chiral centers, there are 2^n possible stereoisomers.
e.g. Compound with 2 chiral centers = 4 stereoisomers.
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Aromatic Compounds
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Aryl compounds or arenes (Ar)
1,2 substituted = Ortho- or 0-
1,3 subst = meta or m-
1,4 subst = para or p-
Physical properties are similar to hydrocarbons.
All 6C atoms are sp2 hybridized.
has delocalized pi electron system.
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Afferent neurons
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Sensory neurons: carry sensory info about external or internal environment TO brain and spinal cord.
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Axial Substituents
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Axial substituents are on Vertical Axis, like axial skeleton.
Axial is NOT favored.
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Action Potential
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If the cell becomes sufficiently excited or depolarized (inside becomes LESS NEGATIVE), an action potential is generated.
Minimum THRESHOLD membrane potential (usually around -50 mV) is level it is initiated.
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Friedel-Crafts Acylation
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A carbocation electrophile, usually an acyl group is incorporated into Aromatic.
Usually catalyzed by Lewis Acids such as AlCl3.
Product = Ar-Acyl group
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Catalytic Hydrogenation
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Reductive process of adding hydrogen to a double bond with aid of a metal catalyst. (platinum, palladium, and nickel)
Product: Alkane with syn addition of H.
Reaction takes place on metal surface, thus H atoms are added to same face (syn addition).
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Combinations
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qCr = q! / [r!(q - r)!]
Possible number of combinations = qCr
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D and L designations
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Based on stereochemistry of glyceraldehude.
If Lowest -OH is on the LEFT, the molecule is L.
If the -OH is on the RIGHT, its D.
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Alcohol + Carboxylic acid --> ?
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Makes an ester
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Conformational isomers
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Compounds that differ only by rotation about one or more single bonds.
(Different positions of a compound)
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Concerted reaction
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Chemical reaction in which all bond breaking and bond making occurs in a SINGLE step.
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CH3COOH + CH3MgBr --> ??
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CH3COO-
Grignard reagents normally convert esters and ketones to alcohols.
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Carbon NMR
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Can show:
1. The number of different carbons with their relative chemical environments.
2. Their number of hydrogens (spin coupled NMR only)
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Reagents used to effect Markovnikov addition to an alkene
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H2O/Cl2
Hg(OAc)2/H2O then NaBH4
H2O/H2SO4
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Addition of X2
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Addition of halogens to double bond.
Rapid process.
Nucleophile is the double bond, which attacks an X2 molecule, displacing X-.
Forms intermediate cyclic halonium ion, which is then attacked by X- to make a dihalo compound.
Anti-addition (attacks SN2).
Product: dihalo alkane
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Parts of Diencephalon
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1. Thalamus
- RELAY and INTEGRATION center for spinal cord and cerebral cortex.
2. Hypothalamus
- Controls VISCERAL function such as HUNGER, THIRST, SEX DRIVE, WATER balance, BLOOD pressure, and TEMPERATURE regulation. Also plays an important role in endocrine system.
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Na+/K+ pump
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Gradients are restored by this pump. It uses ATP energy and transports 3 Na+ out for every 2 K+ it transports into the cell.
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Hyperpolarization
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When a neuron shoots past the resting potential and becomes even MORE NEGATIVE than normal.
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Electrophilic Aromatic Substitution
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Most important reaction of aromatic compounds.
Reaction: electrophile replaces a proton on ring, producing substituted aromatic compound.
Common e.g.:
1. Halogenation
2. Sulfonation
3. Nitration
4. Acylation
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Henderson-Hasselbalch Equation
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pH = pKa - log ([conjugate base]/[conjugate acid])
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Hofmann Rearrangement
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Converts amides to primary amines with the LOSS of the carbonyl carbon.
Involves the formation of a nitrene (nitrogen analog of carbene).
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Meso Compounds
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Have a mirror image that is superimposable.
Thus, NOT optically active.
Have a mirror plane of symmetry
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Gastrointestinal Hormones
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1. Gastrin - stimulates secretion of HCl
2. Secretin - released by small intestine and stimulates secreation of bicarbonate to neutralize acidity.
3. Cholescystokinin - released from small intestine in response to presence of fats and causes contraction of gallbladder and release of bile.
4. Bile - involved in digestion of FATS.
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Grignard Addition
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Grignard reagents (RMgX) add to the carbonyl groups of ESTERS to form KETONES; however, the ketones are more reactive than the initial esters and are readily attacked with more grignard reagent to make TERTIARY ALCOHOLS.
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Dorsal Horn
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sensory info enters the spinal cord through this.
The cell bodies of these sensory neurons are located in the dorsal root ganglia.
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What is the order of electrophiles that E2 reactions prefer?
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3˚> 2˚>1˚
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What do electron withdrawing groups do to nucleophiles?
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Stabilizes them
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How do you rank bases?
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CARDIO
Charge, Atom (size, bigger=more stable) Resonance, Dipole Induction, Orbital
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Which of the following could be the formula for an ester?
a. C6H12O
b. C7H12O2
c. C7H14O
d. C7H16O2
e. C7H16O
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b. C7H12O2
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Amine + (Aldehyde or Ketone) -->
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Product: Imine
Additional reduction with hydrogen in presence of a catalyst (Raney Nickel) = amine.
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Alkyne + O3 -->
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Alkynes can be oxidatively cleaved with ozone to make 2M COOH.
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Unimolecular Elimination (E1)
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TWO step process, proceeding through a carbocation intermediate.
k = [RX] (substrate)
Elimination of leaving group plus proton = double bond.
1. Leaving group departs, producing carbocation.
2. Proton is removed by a base.
E1 is favored by same factors as SN1: highly polar solvents, Weak Nu, highly branched carbon chains (3), and good leaving groups.
However, HIGH temps favor E1.
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Absolute Configuration
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(R) and (S) notation.
- Think of a steering wheel.
- Lowest priority substituent is in fourth position and should point away from you, down the column.
- While #1, 2, and 3 lie on the wheel itself.
- R is clockwise, and S is counterclockwise.
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Aromatic Rings
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Br2 or Cl2
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FeBr3, FeCl3, or AlCl3
(name product)
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Electrophilic Aromatic Substitution of Br or Cl to aromatic ring.
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Which compound will undergo an oxidation reaction without the cleavage of any covalent bond between two carbons?
a. t-butyl alcohol
b. ethyl methyl ketone
c. acetaldehyde
d. acetate
e. all of the above
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c. acetaldehyde
Hydrogen is accessible at the end to oxidizing agent.
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Calcitonin is released from what gland? what does it do?
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Thyroid, decreases calcium concentration in plasma by inhibiting release of Ca2+ from bone.
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Parts of Midbrain
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RELAY center for VISUAL and AUDITORY impulses. Plas an important role in motor control.
Is also called MESENCEPHALON
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Crossing over
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Genes on the same chromosome will stay together unless crossing over occurs.
Exchanges information between chromosomes and may break the linkage of certain patterns. = Mendel's Law of Indenpendent Assortment
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NH3 + ester --> ?
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Answer: amide + alcohol
Nitrogen bases such as ammonia will attack the electron-deficient carbon atom, displacing alkoxide, to yield an amide and an alcohol side product.
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Free radical Additions
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Alternate mechanism for addition of HX to double bond.
Occurs when PEROXIDES, O2, or other impurities are present.
Disobeys Markovnikov rule.
Product: terminal alkyl halides.
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Newman Projection
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Line of sight extends along a carbon carbon bond axis. (Gauge, anti, eclipsed versions)
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Gabriel synthesis
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Converts a primary alkyl halide to a primary amine.
Also a SN2 reaction.
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Define spin splitting in HNMR?
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If two magnetically different protons are within three bonds of each other a phenomenon known as coupling, or splitting occurs.
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HNO3/H2SO4 + toluene --> ?
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R-groups are Ortho-, para- directing, so nitro will add to ortho or para position.
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Types of Gene Regulation in Prokaryotes
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1. Inducible Systems
2. Repressible Systems
Based on accessibility of RNA polymerase.
Directed by OPERON, which consists of structural, operator, and promoter genes.
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Addition of H20
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Water can be added to alkenes under acidic conditions.
Protonated according to markovnikov.
Performed at LOW temperatures.
Product = alcohol
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Resting potential
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At rest a neuron is POLARIZED at -70 millivots.
Which means that the inside is MORE NEGATIVE than the outside.
Due to ionic permeability of the neuronal cell membrane and is maintained by active transport by Na+/K+ pump.
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Aromatic ring + H2/Rh/C and high T/P --> ?
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Benzene --> cyclohexane
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Nuclear Magnetic Resonance (NMR)
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One of the most widely used spectroscopic tools in organic chemistry. NMR is based on the fact that certain nuclei have magnetic moments that are normally oriented at random.
Most commonly used to study H nuclei (protons) and 13C nuclei, but any atom possessing a nuclear spin can be studied.
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Concentration of K+: Is it higher or lower inside the neuron?
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HIGHER than outside.
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What is an epimer?
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A diastereomer with 1 chiral center that is different.
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What is a diastereomer?
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Some chiral centers match, some do not.
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Hydroboration Addition of Alkynes
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Addition to triple bonds is same as double bonds.
Addition is syn and BORON adds first.
Boron can be replaced with proton from acetic acid = cis alkene.
Product: syn alkene.
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Peroxycarboxylic acids (mcpba or m-chloroperoxybenzoic acid)
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Alkenes can be oxidized with mcpba. The products are formed are OXIRANES.
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Homozygous DOMINANT red snapdragons crossed with Homozygous white snapdragons RECESSIVE gives what in F1 progeny? F2?
What type of dominance is this?
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F1 generation will give 100% pink flowers, since generation will give Rr.
F2 will give 1:2:1 progeny in this ratio.
(red, pink, white)
Pink color is result of the combined effects of the red and white genes in heterozygotes.
The type of dominance is called INCOMPLETE dominance because of the pink.
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Bonding Summary (single, double, and triple bonds)
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Single bonds: sigma, sp^3, 109.5 degrees
Double bonds: sigma/pi, sp^2, 120 degrees
Triple bonds: sigma/pi/pi, sp, 180 degrees
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What is the product of the following reaction:
CH3Cl + CH3O-Na+ --> ?
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CH3OCH3
William ether synthesis reaction.
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Alkene + Br2/CCL4 --> ?
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Addition of halogens to double bonds is rapid.
Double bond is nucleophile and attacks X2.
Addition is anti, because X- attacks cyclic halonium ion in SN2 displacement.
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Are chiral compounds optically active?
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No, chiral compounds are not optically active.
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How is blood type determined?
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By three alleles, Ia, Ib, and i.
Only two alleles are present in any single individual, but the population contains all three alleles.
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Reagents used for oxidation of aldehydes
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KMnO4, CrO3, Ag2O, H2O2. The product of oxidation is a CARBOXYLIC ACID.
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Which reagent will give a CIS-product when reacted with an alkyne?
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1. H2, Pd/BaSO4, Quinoline (lindlar's catalyst)
2. a)BH3 b)CH3COOH
both produce cis products.
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Definition of aromtaticity
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(4n + 2) pi
So, can be 2, 6, 10, etc...
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Carboxylic Acid + Alcohols --> ?
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Esters.
Mixtures of COOH and -OH will condense into esters, liberating water, under acidic conditions.
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Free Radical Addition of Alkynes
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Radicals add to triple bonds as with double bonds with ANTI-markovnikov (X-).
Product: trans isomer.
Because intermediate vinyl radical can isomerize to its more stable form.
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What is a racemic mixture?
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1/2: 1/2 enantiomer ratio, so it does not rotate light at all.
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Which of the following would be the best solvent for an SN2 reaction?
a. H2O
b. CH3OH
c. CH3SOCH3
d. heptane
e. tosylate
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c. CH3SOCH3 (dimethyl sulfoxide) gives best results if a polar aprotic solvent is used.
a and b are wrong because these are both polar.
D is a heptane and is incorect because it is a nonpolar solvent.
c. tosylate is a good leaving group not a solvent.
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TTPP x ttpp = ?
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Genotype for all is TtPp and iwll be phenotypically dominant for both traits.
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Note on E2 reactions regarding base used
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Bulkyness of base affects the hydrogen attacked on species. Will attack less substituted if base is bulky.
If base is not bulky, then it will attack most substituted.
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Reduction of Amides --> ?
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Amides can be reduced with LAH to the corresponding AMINE, but NO carbon is lost.
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How can you tell if something is oxidized or reduced?
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More Oxygen = Oxidized,
More Hydrogen = Reduced
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How can you tell if it is an enantiomer or not?
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Enantiomers = exact opposites of chiral centers.
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With molecular formular CH4, how many structural isomers can be formed? C2H6? C3H8? C4H10? C5H12? C6H14? C7H16? C8H18? C9H20? C10H22?
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CH4 = 1
C2H6 = 1
C3H8 = 1
C4H10 = 2
C5H12 = 3
C6H14 = 5
C7H16 = 9
C8H18 = 18
C9H20 = 35
C10H22 = 75
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In order to be meso what does a compound have to have?
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1. Chiral centers 2. A plane of symmetry
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