Resonance
Acidity
Naming
Other stuff
Hybridization
100

Is the lone pair in this compound localized or delocalized?

Localized because there is no resonance

100

What is another term for an electrophile?

Lewis Acid

100

How many methylene groups are present in 2,4-dimethylhexane?

2 methylene groups

100

Which has a lower energy level, bonding or anti-bonding molecular orbitals?

bonding orbitals have a lower energy level, which makes bonds more favorable energetically

100

Calculate the hybridization for all atoms in (CH3)3O+

All carbons and the oxygen are sp3 hybridized

200

What are the 4 rules to consider when determining the major contributor to the resonance structure?

1. fill as many octets as possible
2. make as many bonds as possible
3. the negative charge is on the most electronegative atom
4. as minimal charge separation as possible

200

Which base is stronger, Clor I- ?

Cl- because it is more electronegative

Electronegativity is highest in the upper-right corner of the periodic table 

200

What functional group is contained in CH3CH2OCH2CH3 ?

Ether

200

What is the difference between atomic orbitals and molecular orbitals?

atomic orbitals represent electrons around a single nucleus
molecular orbitals represent electron distribution in a molecule (2+ nuclei)

200

Alkanes are hydrocarbons that only contain ___ hybridized carbons

sp3 hybridized 


300

Draw the resonance structures for CH3NO, indicate the major and minor contributor

Drawn on the board

300

List the following molecules in order of increasing boiling point:

n-hexane
2-methylpentane
2,3-dimethylbutane

2,3-dimethylbutane > 2-methylpentane > n-hexane

Branching decreases boiling point because there is less surface area and therefore less intermolecular attractions (Van der Waals dispersion forces)

300

Write the condensed formula for this compound:


CH3CH2OCH2N(CH2CH3)2

300

Draw the bonding and anti-bonding pi molecular orbitals for O2

drawn on the board

300

What is the bond angle of the sp2 hybridized carbon in this compound?


120 degrees

400

What is the conjugate acid of CH3OH (methanol)?

CH3OH2+

400

What is the IUPAC name of the compound below?

3-Bromo-4-ethyl-2-methylheptane

400

Draw the least stable chair confirmation of:
cis-1-isopropyl-4-methylcyclohexane.

Indicate 1,3-diaxial interactions if they exist

(Chair conformation drawn on the board)

500

Draw two resulting resonance structures of this molecule, there is a + on carbon 1. Indicate the major and minor contributor


drawn on the board

500

Which compound is most acidic?


This compound is the most acidic, determined by drawing the conjugate base and using ARIO factors. Oxygen is more electronegative than Nitrogen, and the second ring does not exhibit resonance.

500

Name 4 functional groups that are found in this molecule

Amide
Alcohol
Amine
Aromatic rings

Not: Ketone, aldehyde

500

Draw the Newman projection for 2,3-dimethylbutane that has 2 Gauche interactions when looking down C2-C3.

What is the torsional energy barrier for this conformation?

E= 3.8kJ/mol + 3.8kJ/mol
E = 7.6 kJ/mol

(Projection drawn on the board)