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49 Cards in this Set

  • Front
  • Back
Conformational Isomers
Geometric Isomers
If isomerism is at a double bond then molecule is achiral.

Examples: Chair, Boat, Twist
Configurational isomers where the isomerism is NOT at a double bond
Results in optical isomers
Diastereomers
Optical Isomer with two or more stereorcenters. (R/S)

DIFF physical properties - b/c of different intermolecular forces

SAME chemical properties
Enantiomers
Optical isomer that is non-superimposable mirror image.

SAME chem properties

SAME physical properties except for rotation of polarized light and some reactions
Conformational Isomers
Same molecule, different orientation.

Staggered, Vs Eclipsed
Staggered - gauche and anti

IDENTICAL CHEM and PHYS properties
Structural (Constitutional) isomers
Same molecular formula, different connectivity

DIFF chemical properties
DIFF physical properties
Sn2 Reaction
Occurs in 1 step (concerted), with a transition state

Rate is bi-molecular k[A][B]

Polar AProtic Solvents

Primary > Secondary > Tertiary because of STERIC hinderance

Optically active / inverted products
Sn1
Occurs in 2 steps (carbocation formation is RDS),

Rate is 1 step : k[A]

tertiary > secondary > primary because of needed carbocation stability

Racemic Products
Good leaving groups
When does the R/S nature of a chiral molecule change in an Sn2 reaction
If the incoming nucleophile has the same priority of the leaving group it will go from R-S or S-R
Which reaction requires STRONG nucleophiles? Sn1 or Sn2
Sn2 - It occurs in one step

Polar APROTIC solvent
Sn1 and E1 reactions often occur _____1_______ and ______2______ with each other under the same reaction conditions
1) Simultaneously

2) Competitively
Is a strong base required for E1 reaction to occur?
No, solvents (PROTIC) can act as the base
are sterics a factor in E2 reactions?
No. Also, E2 is strongly favored by bulky, strong bases (like LDA)
Nomenclature Priority
1) Carboxylic Acid -COOH
2) Ester -COOR
3) Acyl Halide -COX
4) Amide -CONHR
5) Nitrile -CN
6) Aldehyde
7) Ketone
8) Alcohol -OH
9) Thiol -SH
10) Amine
11) Alkene
12) Alkyne
13) Ether
Free radical halogenation steps
1) initiation
2) propagation
3) termination
What are VINYL derivatives
mono-substituted ethylenes

ex: Vinyl Chloride is C=C--Cl
What are ALLYL derivatives
A propene with a substitution on the 3rd C

ex: Allyl Bromide is C=C--C--Br
Formaldehyde
Acetaldehyde
Formic Acid
Acetic Acid
Bond Angle
SP3 - 109.5
SP2 - 120
SP - 180
Huckels Rule for aromaticity
Must be planar and the pi electrons must equal: 4n+2

Example: benzene has 3 double bonds of 2 pi electrons each --> 3x2=6 pi. 4(1)+2=6
Activators
Donate electron density to the aromatic compound adding another conjugated pi bond

Directs ORTHO and PARA

EX: NH3
Deactivators
Withdraw electron density from conjugated system and take away form the conjugated pi system

Directs META

EX: -COOH, -CCl3, -CF3...
Alcohols can be good leaving groups only if you do what
Turn -OH into a good leaving group by:

1) Protonate it
2) Convert it to tosylate
3) Form an inorganic ester
What does PCC do?
It is a mild oxidant. Will oxidize a primary alcohol into an aldehyde, but NOT all the way to a -COOH
What are good oxidizing agents?
Transition metals with lots of Oxygen

Na2Cr2O7, KMnO4, CrO3
What are good ways to synthesize Aldehydes and Ketones?
1) Oxidation of alcohols
2) Ozonolysis of alkenes
3) Friedel-Crafts acylation
Good reducing agents?
turn aldehydes and ketones into alcohols

BEST - LAH, lithium aluminum hydroxide

Good - Sodium Borohydride NaBH4
FORM =

ACET =
FORM = 1 carbon ex: formic acid

ACET = 2 carbon ex: acetic acid
Grignard Reagents
Soap
Decarboxylation
Loss of CO2

Common to dicarboxylic acids and B-Ketoacids

Happens through a 6 member ring intermediate
Friedel-Craft Acylation
Activating ORTHO and PARA directors
Deactivating ORTHO and PARA driectors
Deactivating META directors
What is an anhydride
the condensation dimers of carboxylic acids.

C-CO-O-CO-C

(like a double ketone with an oxygen in between)
Fischer Esterification
amide --> primary amine with CO2 as a leaving group
What does IR spectroscopy measure?
vibrations, in bonds THAT HAVE A BOND DIPOLE!!
Two key IR absorption wavenumbers (1/lambda)
1) OH - 3,300 cm^-1 (broad)

2) C=O - 1,700 cm^-1 (sharp)
5 important H-NMR shifts to know
1) Alkyl
2) Alkene
3) Aldehyde
4) COOH
5) Aromatic
1) 1-3 ppm
2) 4-7 ppm
3) 9-10 ppm
4) 10-12 ppm
5) 6.5-8.5 ppm
Index of H deficiency
n = # Carbons
x = # Hydrogens

Include Halogens as a H
UV spectroscopy
If you see this the molecule has conjugated bonds. The more conjugated bonds the lower the energy of transition
Mass Spectrometer
tallest peak is the 100% abundance reference

Farthest right (M+) (largest M/Z) is the mass of the parent compound minus one electron

Use M+ - the mass of a fragment to know the mass of the piece that broke off
What is used to reduce Nitro compounds to primary amines?
Iron or Zinc in dilute HCl