Organic Chemistry – ACS Final

1680 cm-1 (IR)
amide, C=O stretch
1710 cm-1 (IR)
ketone, C=O stretch
1710 cm-1 (IR)
acid, C=O stretch
1725 cm-1 (IR)
aldehyde, C=O stretch
1735 cm-1 (IR)
ester, C=O stretch
centered 3000 cm-1 (IR)
acid, O-H stretch
centered 3300 cm-1 (IR)
alcohol, O-H stretch
3100-3300 cm-1 (IR)
amide/amine, N-H stretch, NHn where n=# of peaks
2710 & 2810 cm-1 (IR)
aldehyde, C-H stretch
1660 cm-1 (IR)
alkene, C=C stretch
<2200 cm-1 (IR)
alkyne, C triple-bond C stretch
>2200 cm-1 (IR)
nitrile, C triple-bond N stretch
M+2 and M+ same size (Mass Spec)
bromine
M+2 a third as large as M+ (Mass Spec)
chlorine
127, large gap (Mass Spec)
Iodine
odd M+, some even fragments (Mass Spec)
Nitrogen
M+2 larger than usual; 4% of M+ (Mass Spec)
sulfur
~7.2 ppm (HNMR)
aromatic hydrogens, Ph-H
~0.9 ppm (HNMR)
alkane, CH3
~1.7 ppm (HNMR)
allylic, C=C-CH3
~1.3 ppm (HNMR)
alkane, CH2
~1.4 ppm (HNMR)
alkane, CH
~5-6 ppm (HNMR)
vinylic hydrogens, C=C-H
~2-5 ppm (HNMR)
alcohol, -OH
~9-10 ppm (HNMR)
aldehyde, CHO
Brett’s Rule
double bonds cannot be on bridge heads of a bicyclic compound – too much angle strain – unless ring is greater than 8 carbons long
degrees of unsaturation
1/2 (2C+2-H)
where C=carbons, H=hydrogen….X=1 hydrogen, O is ignored and N=1/2 a carbon
no pi bonds (unsaturation)
0 degrees
1 pi bond (unsaturation)
1 degree
triple bond (unsaturation)
2 degrees
formal charge=
# valence e’s – (# nonbonding e’s + 1/2 # bonding e’s)
4 regions of e- density
sp3 hybridization, 109.5 bond angle
3 regions of e- density
sp2 hybridization, 120 bond angle
2 regions of e- density
sp hybridization, 180 bond angle
aliphatic
Pertaining to any member of one of the two major groups of organic compounds, those having straight or branched chain structures.
vinylic
the carbon atoms of a carbon-carbon double bond
higher stability=
lower energy
higher acidity=
higher conjugate base stability
higher acidity=
lower basicity
higher pKa=
stronger base
Zaitsev’s Rule
The most substituted alkene is formed preferentially
Markovnikov
The H atom will always bond to the C with more H
diastereomer
Stereoisomers that are not mirror images of one another
nucleophilicity
decreases across a period and increases down a group
enantiomer
nonsuperimposible mirror images
constitutional isomer
compounds with the same molecular formula but different connections among their atoms
E2
requires a strong (preferrably bulky) base, adds antiperiplanar switching stereochemistry
SN2
requires a strong nucleophile, adds antiperiplanar switching stereochemistry
racemic
In chemistry, a mixture that has equal amounts of left- and right-handed enantiomers of a chiral molecule. (no optical activity)
meso compound
A compound with chirality centers and an internal plane of symmetry causing it to be an achiral molecule
aromatic ring (unsaturation)
4 degrees
aliphatic ring (unsaturation)
1 degree
more branching=
lower boiling point
protic
a solvent with a hydrogen attached to a highly electronegative atom
aprotic
doesnt have H attached to electronegative atom
SN1
tertiary carbons; polar protic nucleophile
E1
tertiary carbons; polar protic bases (bulky)
Gibbs free energy <0=
spontaneous
~18 (pKa)
alcohol
~25 (pKa)
alkyne
~15.7 (pKa)
water
~10 (pKa)
amine
bond dissociation energy
the energy required to break the bond between two covalently bonded atoms (homolytically)
vicinal
substituents attached to adjacent carbons
anti-Markovnikov
electrophile adds to the less substituted carbon