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Exam 1
N/A
49
Organic Chemistry
Undergraduate 2
10/16/2011

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Term
Carboxylic Acid
Definition
Usually smell bad. R-COOH. http://upload.wikimedia.org/wikipedia/commons/thumb/b/b5/Carboxylic-acid.svg/150px-Carboxylic-acid.svg.png
Term
Dipole moment (μ)
Definition
Add vectors (arrows) of all dipoles in molecule.
Term
Rules of resonance
Definition
Only move unshared pairs or double/triple bonds. Curved arrows. Keep octet of O, N, and Group 7. Never exceed octet of Z ≤ 10. Always put charges ≠ 0. If original is neutral, only 1 pos and neg charge can be added each. If original = ion, no new charges added.
Term
Resonance stability
Definition
Gives more area for e- to move around, more stable b/c less NRG.
Term
Nitrile
Definition
RCN http://upload.wikimedia.org/wikipedia/commons/thumb/6/67/Nitrile-group-2D.png/150px-Nitrile-group-2D.png
Term
Thiol
Definition
RSH. Sulfur analog of alcohols. http://upload.wikimedia.org/wikipedia/commons/thumb/9/92/Mercapto_Group_General_Formulae.png/120px-Mercapto_Group_General_Formulae.png
Term
Aldehyde
Definition
RCHO. http://upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Aldehyde.svg/150px-Aldehyde.svg.png
Term
Ketone
Definition
RC(=O)R'. http://upload.wikimedia.org/wikipedia/commons/thumb/4/40/Ketone-group-2D-skeletal.svg/150px-Ketone-group-2D-skeletal.svg.png
Term
Amine
Definition
Primary: http://upload.wikimedia.org/wikipedia/commons/thumb/7/7e/Primary-amine-2D-general.png/100px-Primary-amine-2D-general.png. Secondary: http://upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Secondary-amine-2D-general.png/100px-Secondary-amine-2D-general.png. Tertiary: http://upload.wikimedia.org/wikipedia/commons/thumb/1/1e/Amine-2D-general.png/100px-Amine-2D-general.png. Quaternary: http://upload.wikimedia.org/wikipedia/commons/thumb/9/92/Quaternary_ammonium_cation.svg/220px-Quaternary_ammonium_cation.svg.png.
Term
Amide
Definition
R2NCOR. R-C=O linked to N. http://upload.wikimedia.org/wikipedia/commons/thumb/2/2e/Amide-general.png/180px-Amide-general.png.
Term
Nitro
Definition
RNO2. http://upload.wikimedia.org/wikipedia/commons/thumb/6/62/Nitro-group-2D.png/150px-Nitro-group-2D.png
Term
Most typical resonance moves
Definition
1) lone pair to single bond = double bond. 2) double bond to atom = single bond + lone pair on atom. 3) double bond to single bond = single bond + double bond. 4) lone pair to double bond = triple bond. 5) triple bond to atom = double bond + lone pair on atom. NEVER move C=C to make C-C: if that's the only move.
Term
Degrees of Unsaturation
Definition
DOU = (2C + 2 - H - X + N)/2 Ring consumes 1 DOU, double bond consumes 1 DOU, triple bond consumes 2 DOU.
Term
Sulfide
Definition
CSC. Sulfur analog of ether. http://upload.wikimedia.org/wikipedia/commons/thumb/e/ec/Thioether_structure.svg/140px-Thioether_structure.svg.png
Term
Eyring equation
Definition
Rate (k) that A is transformed to B @ 25degreesC. K = (6.21x10^12)e^(-0.404(ΔE/s)). K = s^-1. ΔE = kJ/mole (NRG of activation). ΔE = diff. between one NRG height and another; use Estrains to get diff., take into account positions you have to go through to get there.
Term
Conformational isomers
Definition
Isomers where a group undergoes internal rotation. At any point of rotation.
Term
Types of motion
Definition
Translational: movement of center of mass, shuffling. Virational: lengthening & shortening of bonds & bond angles. Rotational: about center of mass or internally (body part).
Term
Torsional/Eclipsing strain
Definition
By close approach of e- not involved in same chemical bond (e-'s take up each other's space).
Term
Steric strain
Definition
By 2 objects trying to occupy same space @ same time. I.e., big molecules in same plane.
Term
Carbonyl, methyl, methylene, methine
Definition
Not free-standing functional groups, but referred to. Carbonyl: C=O, http://upload.wikimedia.org/wikipedia/commons/thumb/c/ce/Carbonyl-general.png/150px-Carbonyl-general.png. Methyl = CH3. Methylene = CH2. Methine = CH.
Term
Ether
Definition
COC. http://upload.wikimedia.org/wikipedia/commons/thumb/5/51/Ether-%28general%29.png/150px-Ether-%28general%29.png
Term
Halide
Definition
Group 7 binded to a C. Superprimary = X-CH3. Primary = X-CH2-C. Secondary = X-CH-C2. Tertiary = X-C3.
Term
Alkyne
Definition
R-C≡C-R.
Term
Arene
Definition
Benzene ring. Very thermodynamically stable, low NRG. http://upload.wikimedia.org/wikipedia/commons/thumb/0/07/Benzene_circle.svg/100px-Benzene_circle.svg.png
Term
Alkine
Definition
C=C. Unsub = H2C=CH2. Monosub = CHC=CH2. Disub = C3=CH2. Trisub = C3=C2H. Tetrasub = C3=C3, most stable.
Term
Ester
Definition
RCOOCH3, RCO2CH3. http://upload.wikimedia.org/wikipedia/commons/thumb/3/34/Ester-general.svg/130px-Ester-general.svg.png
Term
Plotted Estrain
Definition
Made from values of Estrain for each rotaton position (eclipsed, gauche, anti). Hills = eclipsed, valleys = staggered. Valleys are preferred - lower NRG.
Term
Eclipsed conformation
Definition
Bonds off of C's are directly lined up, e- clouds will overlap, very unstable.
Term
Staggered conformation
Definition
Bonds off of C's are alternated, not directly lined up. Results in anti and gauche.
Term
Newman projections
Definition
Shows rotations about σ bonds. Sight down a C-C bond w/substituents shown. http://upload.wikimedia.org/wikipedia/commons/8/80/Newman_projection_butane_-sc.png
Term
Bond-length strain
Definition
By deviation of bond from its optimum length. Any deviation = less stable, higher NRG.
Term
Bond-angle strain.
Definition
Deviation from ideal bond angle.
Term
Normal bond # of atoms
Definition
C = 4. N = 3. O = 2. H = 1. X = 1.
Term
Alcohol
Definition
COH. http://upload.wikimedia.org/wikipedia/commons/thumb/0/02/Alcohol.png/180px-Alcohol.png. If C bonded to 0 other C, superprimary. C bonded to 1 C, primary. C bonded to 2 Cs, secondary. C bonded to 3 Cs, tertiary.
Term
Modification of bond length and strength
Definition
If one resonance = double/triple bonds, overall structure has those properties; shorter and stronger bond than a single bond would be.
Term
Modification of hybridization state
Definition
Steric # prediction drops down one if atom can participate in resonance.
Term
Rank of resonance structures
Definition
1) octet on all atoms. 2) more covalent bonds. 3) less formal charges. 4) opposing charges closer together. 5) + on less χ, - on more χ.
Term
Bond-line notation
Definition
Zigzags, C skeleton, doesn't have to include Hs and lone pairs. http://upload.wikimedia.org/wikipedia/commons/thumb/b/bd/THC_structure.svg/200px-THC_structure.svg.png
Term
Electronegativity
Definition
Increases diagonally toward F. Ability to attract e-. H is between B&C.
Term
Showing dipoles
Definition
δ+/- on less/more χ atom. OR arrow w/+ over less χ atom: http://chemwiki.ucdavis.edu/@api/deki/files/4754/=dipole.jpg. Unit = Debye (D).
Term
Dash and wedge
Definition
Solid line = plane of paper. Dashed = pointing into paper. Wedge = pointing toward you. Unshared e- ignored.
Term
σ vs. π
Definition
Pi = double/triple bonds, side to side interactions. Sigma = single bonds, always one per bond group, head to head interactions.
Term
Ionic bonds
Definition
Complete transfer of e- from metal to nonmetal.
Term
Sp3, sp2, sp
Definition
Predict w/ steric #, sp^(SN-1) (SN = # atom bonded - # unshared pairs). sp^(SN-2) if participates in resonance. Sp3 = 109.5, tetrahedral, chicken foot. Sp2 = 120, same plane, perp. to 1 p. Sp = 180, perp. to 2 p's.
Term
Polarity
Definition
Less χ = less e-,
Term
Difference in χ and bond type
Definition
<0.5 = nonpolar covalent. 0.5-1.9 = polar covalent. >1.9 = ionic.
Term
Formal charge
Definition
FC = group # - # unshared e- - # bonds
Term
e- affinity
Definition
NRG required/released by gaining e-. Neg = releases NRG, more stable, wants e-. Pos = gains NRG, less stable, doesn't want to gain e-. Group 8 doesn't want to lose/gain e-.
Term
Ionization Potential
Definition
X --> X+ + e-, ΔE = IP Always positive - must add NRG to remove e-. More NRG required to lose e-, less atom wants to give up its e-.
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