Transcript Organic Chemistry: 1828

Wilkommen nach
Organische
Chemie Klasse
ORGANIC-SPEAK
IN A NUTSHELL
GOT IT ?
OH
?????
+
NH
OH
OH
85% H3PO4
Br2 /wet CCl4
pcc neat
Br
reflux
O
O AlBr3 (anhyd.)
SOCl2 (neat)NH (anhyd.)
3
OH
NaBH4
NHNH
Al/Hg
NaOH
NH2
N-methylphenyl-2-propan-2-amine
Recognize the
Final product ??
Pop culture hint
NH
149.2=MW
Common name:
methamphetamine
Street name:
Crystal meth
Hydride transfer mechanism for Cannizzaro reaction
1)
2)
3)
Got it ?
The Twin Language Skills of
Modern Organic Chemistry
1. Synthesis
2. Mechanism
MECHANISM + SYNTHESIS
Wilkommen
nach
Organische
Chemie Klasse
= ORGANIC CHEMISTRY
But wait…there’s more !!
Breaking Bad :Season 1, episode 1 time 40:51-43:17
GOT IT ?
In the beginning….1828
 Vitalism
Theory of Matter dominates
1) Matter is divided into organic and inorganic
2) Only living things can create or generate organics
3) Inorganic matter lacks the `essences of life’ =
`in vivo’ (of life) quality present in organic matter.
1828
 Chemistry is the down-trodden, lower class
stepchild of medicine
This tough-looking cookie works for free
as the chief chemist of the Stockholm
School of Medicine
Johann Jakob Berzelius
A `father’ of modern
chemistry
The Big Breakthrough in 1828
pg. 2 of text
The kid’s big breakthrough…
CH4N2O

CH4N2O
heat
NH4OCN

(NH2)2CO
heat
Friedrich Wohler, boy
chemistry wonder
becomes Berzelius’s
(unpaid) grad student
Inorganic salt Urea
(essence
(ammonium
of urine)
cyanate)
1835
Vitalism is road kill on the highway of chemistry
RIP :
VITALISM
THEORY OF
MATTER
1835
Though vitalism is dead…things are
maybe worse
“Organic chemistry nowadays drives me
mad. To me it appears like a primeval
tropical forest full o the most remarkable
things, a dreadful endless jungle into which
one does not dare enter for there seems to
be no way out.”
Friedrich Wohler (former boy wonder)
1835
 Footnote: chemists are still poor vs. doctors but all doctors
must take organic chemistry
Methane as described in general
chemistry
1) CH4= 25 wt % H + 75 wt % C
2) 1 mole CH4 = 1 mole C + 2 moles H2
3) C(s) + 2H2(g)  CH4(g)
-17.7 kcal/mol CH4
4) CH4(g) + 2O2(g) CO2(g) + 2H2O(l) -191 Kcal/mol CH4
5) R(C-H) = 10.9 nm; (H-C-H)=109.5o
6) mp= 90 K; bp= 102 K
Number
heavy
Methane according to organic chemists
1)
4) Main source:
biological decay
5) Main reaction of CH4:
Free radical halogen (X)
2) Bonds are
substitution
sp3 hybrids
light
CH4 + X2  CH3X + HX
3) Smallest member of
alkane family: CnH2n+2
Organic chemists
think a lot like….
zoologists
1) What does the animal
methane look like ?
2) vertebrate/invertebrate?
bonds are sp3 hybrids
3) What family of
chemical critters
does methane
belong to ??
Smallest member of
alkane family: CnH2n+2
4. Where does this methane
animal main live???
oil
5) What happens when methane meets
with other chemical critters ?
5) Main reaction of CH4:
Free radical halogen (X)
substitution
light
CH4 + X2  CH3X + HX
For the mathphobic, Organic is
the place to be…
Organic is visual and verbal,
not mathematical* (except in
advanced courses)
* Except in lab where % yield and mole
count rears their nasty heads
More tloc*: organizing the jungle’’
more `zoological’ thinking
Thinking Like
an Organic
Chemist
functional’ group organizational
scheme for organic chemistry
`
Alkynes ( )
Alkenes (=)
Alkanes (
Chain
aliphatics
)
R-H
• R-OH alcohols
• R-X alkyl halides
(X=F,Cl,Br,I…)
• R-NH2 amines
Ring
aliphatics
aromatics
OIL and COAL
(dead plants and animals
under pressure and low O2)
Biology
Extended`phylogeny’ of organic compounds
Organic-bioorganic divide
lipids
sugars
Bio molecules
ketoesters
diones
ketones
alcohols
halides
Carboxylic
acids
amines
heterobenzenes
alkenols
phenols
dienes
alkenes
napthalenes
benzoates
haloalkenes
alkanes
DNA
proteins
anthracenes
alkynes
Chain aliphatics
Mono rings
Ring aliphatics
Fused rings
aromatics
OIL and COAL
(dead plants and animals under pressure and low O2)