Quiz

6-10: 3 people

11-15: 8 people

16-20: 8 people

21-25: 9 people

This is the highest average of any quiz.

The hour exam has more material but only twice

Covers Ch 1-7

aspects of the Hydrogen PAC naming system

Structure, write out correct IUPAC name

• If structure is given, make sure the structure is not steriochemistry
• If the structure is steriochemic, then you need to include the steriochemistry
• eg trans-2-methylethyl-cyclopentane
  • this is the same as trans-1-ethyl-2-methyl-cyclopentane

• These are sorted by 'I'
  • isobutyl
  • isopropyl
• These are sorted by 'B'
  • sec-butyl
  • tert-butyl

H-Br + alkenes in presence of peroxides

• eg 1 butene+HBr (without peroxides) = 2-bromobutane
• eg 1 butene+HBr (with peroxides) = 1-bromobutane
  • non-Markonikov reaction

C-H (solvent) bonds + O2(unpaired e-) = C-O-O-H (hydroperoxide)

also C-C + O2 = C-O-O-C

ROOH RO + OH free radical (no charge on these)

• (result in a homolysis type of process)
• formal chare = [# val e- free atom = G#] - sum[#nonbonded e- + # bonds to atom]
  • RO charge = 6-(5-1) = 0
  • OH charge =

RO + HBr starts a chain mechanism

• Hydrogen abstraction; HBr breaks down and you end up with H atom + Br atom
• RO + HBr -> ROH + Br
• Br attacks alkene; you end up with a alkene free radical BrH2C-CH-CH2+CH3 (no charge, but highly reactive because of the missing H on C#2
• another HBr comes alone and adds the H to the second C, leaving another Br floating around to start the next.

Conformational analysis

• acyclic structures
• cyclohexane ring (chairs, etc)

Newman Projection

• very important tool to use

1. 1. Identify groups or atoms that are attached to the 2 bonds.
2. 
   

• review gauche staggered conformations
• review anti conformations
• least stable is eclipsed with 2 groups on top of each other.
• tortional interactions: staggered vs eclipsed (staggered more stable)
• steric interactions: anti vs gauche (gauche more stable)

"Ring Flip"

• IUPAC name draw more stable chair configuration
  • draw Haworth projection (flat ring)
  • make a model
  • relax it and draw one chair
  • flip it and draw another chair

• eg cis-1-t-butyl-3-ethylcyclohexane
  • make a squashed hexagone
  • put the #1 C at the end (not required)
  • put tButyl at 1
  • put Ethyl at 3
    • these are cis, so both up (or both down)
  • then unsquash hexagon
  • then flip
    • which is the best way to go (least energetic)?
    • (the flipped orientation)

You may use the model kit with pre-built models on the exam

E/Z will be on the exam

• E-2,4-dimethyl-3-hexene
• This is similar to the cis/trans nomenclature, but you can't use cis/trans due to the lack of non H bond on the -ene