1. Targets of Organic Chemistry I & II
Reactions
Mechanism
Structure: bonding
(analysis)
Targets of Organic Chemistry I & II
Organic
Compounds
OrgChem-Chap12

2. 공 부 하 는 방 법
“그저 익숙하도록 읽는 것뿐이다. 글을 읽는 사람이, 비록 글의 뜻은 알았으나, 만약 익숙하지 못하면 읽자마자 곧 잊어버리게 되어, 마음에 간직할 수 없을 것은 틀림없다.
이미 읽고 난 뒤에, 또 거기에 자세하고 익숙해질 공부를 더한 뒤라야 비로소 마음에 간직할 수 있으며, 또 흐뭇한 맛도 있을 것이다.” - 퇴계 이황 (금장태 著)
OrgChem-Chap12

3. Chapter 12 Functional Groups II
Organic Chemistry II
Fall 1999
Chapter 12 Functional Groups II
“a group of atoms where the reaction takes place”
arenes: aromatic hydrocarbons,  466 bottom
aromatic: fragrant odor & very stable ( 469 top)
non-polar, high mp, wide occurrence:  469 middle
benzene
ethylbenzene
o-xylene
biphenyl
OrgChem-Chap12
Chapter 11

4. Arenes (continued) arenes: aromatic hydrocarbons
Organic Chemistry II
Fall 1999
Arenes (continued)
arenes: aromatic hydrocarbons
parent name: benzene, toluene, etc.  467 bottom
disubstituted: o-, m-, p- or numbering (1,2-, 1,3-, 1,4-)
as substituents: phenyl (Ph), benzyl (Bn), tolyl
practice:  468, Problems 12.1 & 12.2
Focus On:  469, structure proof for dibromobenzene
OrgChem-Chap12
Chapter 11

5. Phenols:  472 parent name: phenol or common names
Organic Chemistry II
Fall 1999
Phenols:  472
phenol
catechol
phloroglucinol
parent name: phenol or common names
practice:  472-3, Problem
 3 x 109 lbs/yr: disinfectant, bisphenol A
stronger acid (pKa  10):  473 top 12.6
OrgChem-Chap12
Chapter 11

6. Aldehydes & Ketones:  473 the longest chain with a carbonyl group
Organic Chemistry II
Fall 1999
Aldehydes & Ketones:  473
carbonyl group
acetaldehyde
benzaldehyde
acetone
acetophenone
the longest chain with a carbonyl group
alkanal/alkanone:  & Problems
acidic a-carbon: pKa  20,  476 middle
polar (ether<bp<alcohol) & basic (H-acceptor)
practice:  476 Problems
pleasant odors but easy oxidation:  477 top
OrgChem-Chap12
Chapter 11

7. Carboxylic Acids: RCO2H
Organic Chemistry II
Fall 1999
Carboxylic Acids: RCO2H
carboxy(l) group
acyl group
malonic acid
terephthalic acid
phenylacetic acid
alkanoic acid:  477 & 478, Prob
more polar & hydrogen bonding: high mp & bp
acidic proton: pKa  5,  479 top
AcOH ( 3 x 109 lbs/yr), aspirin, ibuprofen:  479
OrgChem-Chap12
Chapter 11

8. Carboxylic Acid Derivatives (I): RCO-Y
Organic Chemistry II
Fall 1999
Carboxylic Acid Derivatives (I): RCO-Y
parent name: alkan(o)ic acid,  480 Table 12.1
acryloyl chloride
succinic anhydride
ethyl acetate
N,N-dimethylformamide
acetonitrile
monosodium glutamate
(MSG)
practice:  483~4, Problems 12.14~5
OrgChem-Chap12
Chapter 11

9. Carboxylic Acid Derivatives (II)
Organic Chemistry II
Fall 1999
Carboxylic Acid Derivatives (II)
characteristics: mp & bp,  484 Table 12.2
amides: charged resonance structure,  484
practice:  485 top, Problem 12.16
natural abundance:  485-6
rare: acid halide, acid anhydride, nitrile
Focus On: fragrance & flavor,  487 top
ester hydrolysis & oxidation of aldehydes:  488 bot
OrgChem-Chap12
Chapter 11

10. Sulfur Compounds sulfur vs oxygen: 2-, 3-, 4-, & 6-valence (d orbital)
Organic Chemistry II
Fall 1999
Sulfur Compounds
sulfur vs oxygen: 2-, 3-, 4-, & 6-valence (d orbital)
RSH: thiols (mercaptans); alkanethiol,  489 top
stinky odor, stronger acid, better nucleophile
R-S-R’: sulfides; alkylalkyl sulfide
sulfoxides & sulfones: DMSO (very polar),  489 mid
sulfonic acids: strong organic acid,  490 top
derivatives: similar to those of carboxylic acid derivatives
practice:  491 Problems 12.17~18
OrgChem-Chap12
Chapter 11

11. Phosphorus Compounds P vs N: 3-, 4-, 5-valence,  490 bottom
Organic Chemistry II
Fall 1999
Phosphorus Compounds
P vs N: 3-, 4-, 5-valence,  490 bottom
PH3: phosphine, a toxic gas with bad odor
PPh3: good nucleophile & transition metal ligand
(RO)2P(O)OH: phosphate, backbone for RNA/DNA
phosphatidylcholine: constituent of membranes
OrgChem-Chap12
Chapter 11

12. Priority of Functional Groups
Organic Chemistry II
Fall 1999
Priority of Functional Groups
3-cyano-7-hydroxy-4-octenal
ethyl 3-oxobutanoate
(ethyl acetoacetate)
order of priority:  492 Table 12.3
common name: often more convenient,  494
practice:  Problems 12.19~20
OrgChem-Chap12
Chapter 11