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Hydroxyl Compounds: Preparation & Reactions

The document summarizes reactions of hydroxyl compounds and phenols. It discusses several methods for preparing hydroxyl compounds including reduction of carbonyl groups and hydration of alkenes. It also outlines common reactions of aliphatic and aromatic alcohols such as esterification, oxidation, and dehydration. Specific chemical tests are described for identifying phenols, including their reactions with bromine water and iodoform formation.

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Chris Lau
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2K views1 page

Hydroxyl Compounds: Preparation & Reactions

The document summarizes reactions of hydroxyl compounds and phenols. It discusses several methods for preparing hydroxyl compounds including reduction of carbonyl groups and hydration of alkenes. It also outlines common reactions of aliphatic and aromatic alcohols such as esterification, oxidation, and dehydration. Specific chemical tests are described for identifying phenols, including their reactions with bromine water and iodoform formation.

Uploaded by

Chris Lau
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
  • Reactions of Aliphatic Alcohols: Explores the chemical reactions involving aliphatic alcohols, including dehydration, substitution, and oxidation processes.
  • Preparation of Hydroxyl Compound: Details the methods and chemical reactions used in preparing hydroxyl compounds, such as reduction and Grignard reactions.

Chapter 17 Hydroxyl Compound SMK Sacred Heart, Sibu

1. Preparation of hydroxyl compound


Reduction of C=O bond (i) LiAlH4 in dry ether, (ii) H3O+,
Na in C2H5OH
H2, Ni, 180oC ,(Not suitable for aromatic compounds)
(i)NaBH4, ethanol (ii)H3O+, (For aldehyde & ketone)
Alkaline hydrolysis of haloalkanes, R-X + NaOH(aq)
+H2O(g), conc H3PO4, 300oC, 60atm
Hydration of alkenes, C=C
(i) Conc H2SO4, rtp (ii)H2O,
RMgX + H2C=O
Reaction of Grignard reagent RMgX + RCH=O
RMgX + RRC=O

2. Reactions of Aliphatic alcohol 2. Reactions of Aromatic alcohol (Phenol)


n e o w +HX SCl i +NaOH(aq) ONa
+Na ONa
n Na metal, r.t.p
R-OH + Na R-ONa + H2 +RCOCl OCOR
e Esterification
(a) RCOOH, , conc H2SO4
(b) RCOCl, rtp
-OH group is Ortho and Para director
Remove H2
o A)Oxidation +Cl2, dry AlCl3
C-OHC=O
Insert O btw C-H Conc H2SO4,
KMnO4/H+
+RX, dry AlCl3
1o RCOOH
2o RCOR +RCOCl, dry AlCl3
3o No reaction +HNO3
Remove H2
B) Dehydrogenation
C-OHC=O
Cu, 300oC
dilute Concentrated
1o RCHO
2o RCOR OH OH OH
3o C=C (Remove H2O) NO2 O 2N NO2
-w Dehydration +
(a) Conc H2SO4, 180oC Remove H2O
(b) Al2O3, C-OHC=O
NO2 NO2
+HX Lucas reagent (Conc HCl, ZnCl2)
(a) Conc H2SO4, 180oC Chemical test for phenol
(b) Al2O3,
R-OH + HCl R-Cl + H2O Add Br2(aq) or Cl2(aq)
1o no cloudiness at rtp Observation: White solid
OH
2o cloudiness after 5 min
Br Br
3o cloudiness immediately
SCl Cl substitution (Conc HCl, ZnCl2)
(a) PCl5 / SOCl2 R-OH R-Cl
i Iodoform test (I2 in NaOH(aq), warm) Br
H
R C OH R C O Fission of RO-H bond neo
CH3 ONa Fission of R-OH bond -w +HX SCl i

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