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R H R H R H
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2

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C N N C + N2
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OH

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H3C CH2 O H + HO CH2 CH3 H3C CH2 O CH2 CH3

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→
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6

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6
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2
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O $ P

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K
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R
H2
∆
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R

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X
X Na

%
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H H

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N
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H3 C
OH OH

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-9>*;*-9( +
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H3C H 3C

Zn/H2O
O O
H 2C C + C H
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OH

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n
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C
n
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H H

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2)c-B9*c-B

X X
H 3 C C C H 3C H 3C C C H 3 C
H H H H

OH
H
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ROH

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Zn
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'
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+
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χ <χ

&

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µ
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+
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+
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A-B A

H3C C 2H5 H3C C 2H 5 C2H 5

A:B B C2H5
C C C C H 3C C C C C
B A A B A H 3C A
cis
trans

(2;;*-9( +
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H2/Pd(Pb)
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ν
HBr/hν
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142+
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Hg(II)/H2O/H+ ceto-enolica
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2 HC CH H2 C CH C CH
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+
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+
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CuC2/Bi/SiO2
HC CH + 2 HCOH(aq) HOH2C C C CH2OH

K
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20@4(9- +
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KOH/R-OH
H H NaNH2
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X X X CH3

+2)7*)+
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∆
Carbón Coque
2000º C H2O
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+
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E+;7(
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292
5 5 +
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Oxd
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cat/H+/H2O

CH2 OH
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O H O
H
H
fermentacion
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OH H
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OH
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H OH

0
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O
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K
KMnO4, K2Cr 2O7, Ag(NH4)2 +, ... R' = H HO
C O
R
-O
Oxidación

NaOH/I2 R' = CH3

CHI3 + C O
R H
-O
R' OH-cc R = sin Hα R' = H
C O C O + R C OH
R R H
Reducción

H2/Pt, LiAlH4/H+ R' H

C
R OH

Zn-Hg/HCl cc R' H
C
R H !

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C O
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C C
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R' R'
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H

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R C
O
R' C
O O
O φ / AlCl 3
H-φ
R C + R' C
φ OH N
 3 +
•Lafonte, O.; Mayrarque, J. y Vayssiers, M. "Ejercicios de Química Orgánica". Ed.
Paraninfo

•Mayer, L. “Métodos de la Industria Química Orgánica” Ed.. Reverté, S.A.

•Meisleich, H.; Nechamkin, H. y Sharefkin, J. “Química Orgánica”. Ed. McGraw Hill

•Morrison, R.T. y Boyd, R.N. "Química Orgánica". Ed. Addison-Wesley Iberoamericana

•Quiñoá, E. y Riguera, R. “Cuestiones y Ejercicios de Química Orgánica”. Ed. McGraw

Hill

•Tedder, J.M.; Nechvatal A. y Jubb, A.H. "Química Orgánica: Un método mecanicista"

Ed. Urmo

•Weissermel, K. y Arpe, H.J. “Química Orgánica Industrial”. Ed.. Reverté, S.A. N