Organic Chemistry 2nd Quarter

Organic Chemistry 2 with Furge at Kalamazoo College

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By: Wyatt Smith
Created: 2012-01-09
Size: 28 flashcards
Views: 22

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PCC

Mild Oxidant:

1˚ Alcohols will form an aldehyde

2˚ Alcohols will from a ketone

3˚ Alcohols = NO RXN

Metal-Oxygen Bonds

used to oxidize alcohols. Can not be used to oxidize alkenes
used in conjunction with H2SO4 and H2O
Usually Chromate in 6+ oxidation state or Manganese

1˚ Alcohols form a carboxylic acid

2˚ Alcohols will form a ketone

3˚ Alcohols = NO RXN

Amberlyst A26 Resin

Exactly like the Metal-Oxygen Oxidizers.

More easily recoverable than those oxidants.

1˚ Alcohols form an aldehyde

2˚ Alcohols will form a ketone

Ozonolysis

Uses O3 to break C=C and form C=O (ketones)
Each carbon in a C=C bond forms a ketone.
Used to open rings and form ketones.

Sharpless Reagent

Reagent used when attempting to create an enantiomeric selective epoxide.
Used solely on allylic alcohols
Draw with OH group in the lower right of the plane and then attach epoxide.
(-) DET and (+) DET add epoxide group from above or below respectively.

Lindlar Catalyst

Catalyst developed to halt the hydrogenation of alkynes.

Halts the process at an alkene
Cis alkynes become cis alkenes
trans alkynes become trans alkenes

Common Oxidizing Agents

Chromium (IV) oxide (CrO3)
Na2Cr2O7
K2Cr2O7
KMnO4
OsO4
Ag2O

H2 and Pd, Pt, or Ni-C

Palladium absorbed on carbon
Facilitates the addition of Hydrogen to an alkene, reduces it.
H2 adds in a syn fashion.

Conjugation

When two pi bonds are separated by a sigma bond.

Equally when three pi orbitals are shared over 3 carbons

Lowers the Heat of Hydrogenation

Increases stability

Diels-Alder Reaction

Reaction involving an diene and a dienophile

always forms a hexene

more polar substituents on the dienophile promote reaction

electron withdrawing groups increase the speed of the reaction only on dienophiles (property is inversed for diene)

Endo product

Diels-Alder product where substituents are closer to the upper bond.

Exo product

Diels-Alder product where substituents are oriented farther from the upper bond (preferred orientation)

Aromatics

1. Cyclic

2. Planar

3. Completely conjugated

4. Huckel's Rule

A molecule's pi electrons are equal to 4n (where n is the number of ∏ electrons) + 2 ∏ electrons

Toluene

Methyl group attached to a Benzene ring.

Aniline

Amine group attached to a Benzene ring.

Phenol

Alcohol group attached to a Benzene ring.

Disubstituted Benzene

Benzene's that have two different groups.

Ortho Benzene

1,2-di(group name)benzene
o-di(group name e.g. chloro, bromo)benzene
ortho-di(group name)benzene

Meta Benzene

meta-di(group name)benzene
m-di(group name)benzene
1,3-di(group name)benzene

Para Benzene

para-di(group name)benzene
p-di(group name)benzene
1,4-di(group name)benzene

Aromatic Naming Rules

Number to give the lowest possible numbers around the ring
Alphabetize the substituent names
When substituents are part of common roots (e.g. Phenol) name the molecule based on benzene. The substituent that comprises the common root is located at C1

Anti-aromatic

Molecules that are cyclic, planar, and completely conjugated but do not have 4n + 2π electrons.
Are exceptionally unstable.

Annulenes

Hydrocarbons containing a single ring with alternating double and single bonds

Naming Annulenes

Place the number of π electrons in front of the name.

[# of π electrons]-Annulene

Naming Benzene Substituents

Name with common name if it is present.
Number to have the lowest # possible
Name in alphabetical order

Two Substituents on Benzene

If common name exists use it first and then name other substituent with lowest numbering.

Characteristics of Benzene

Incredibly stable
Undergo substitution rxns, NOT addition
All e- are distributed across the p orbitals

≥ Two substituents on Benzene

Cannot use p-, o-, or m- to describe it.
Can still use the common name
# so substituents have the lowest #
alphabetize them in the name

About this deck

By: Wyatt Smith
Created: 2012-01-09
Size: 28 flashcards
Views: 22

About StudyBlue

“Simply amazing. The flash cards are smooth, there are many different types of studying tools, and there is a great search engine. I praise you on the awesomeness.”
Dennis