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CHEM3580 Organic Chemistry

Professor Dotsevi Sogah

Week 1: Lecture 3 of 3
Friday, January 23, 2009
10:06 AM

Cue Column:
• Announcements

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• Summary of today's lecture

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• Lecture begins:
I. Benzene ring:

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a. Outside of ring:
25 i. Net higher field
ii. Higher frequency
iii. Higher chem shift
iv. DOWNFIELD
b. Inside of ring
30 i. Net lower field
ii. Lower field
iii. Lower chem shift
iv. UPFIELD

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• EX1: triple bonds

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a. So treat triple bonds the same as single bonds

45 • Ex2:

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55 a. # of pi bonds? If aromatic, the 2 H's inside will be upfield

b. If NMR data confirms this, then molecule is aromatic

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Aromatic? Cannot guess,

Not aromatic
Satisfies 4n+2 rule
70 Not planar: b/c inside strain
NMR shows alkene characteristic, not aromaticity

UNDERSTAND STABILITY OF COMPOUNDS , this will underline everything we do in

75 this course

II. Consequences of aromaticity

a. Effect on pKa

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 a. Effect on pKa

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b. Ex

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c. ex

d. ...

a. Which electron pair is more easily protonated?

i. Put it in acid, will the outside hydrogen go to top N or bottom N?
ii. It will go to the N that is NOT involved in the aromaticity, the top one.

a. Stability of intermediates

a. .hammonds postulate: more stable intermediate forms faster

i. More stable, will form larger amount, which also means form faster

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III. Rxns on Benzene
a. Will not ask us to name compounds, BUT will put names of compounds in questions, so you must be
able to identify compounds
b. Nomenclature:
i. Products of benzene forms, Name them as a derivative of benzene

ii. Di-substituted

a. Numbering the ring

i. Use order that will give LOWEST numbers

b. Benzene As a substituent

c. Reactions
i. Benzene does NOT react like alkenes

ii. ...

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 d. ...

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END

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