CHEM 219 MODULE 5 EXAM TEST PAPER
WITH DETAILED QUESTIONS AND
RELIABLE ANSWERS
◉ Conversion using Phosphorous Halides (PX3)
Answer: X= Cl or Br
- Alcohol (3R-OH) + phosphorous trihalide (X2P-X) —> alkyl
halide (3R-X) + H3PO3
-particularly efficient as one molecule of PX3 can convert 3
molecules of alcohol to the corresponding alkyl halide
-byproduct of the reaction is phosphorous acid
◉ Conversion using Thionyl Chloride (SOCl2)
Answer: Alcohol (R-OH) + Thionyl Chloride (Cl-S=O-Cl) —> alkyl
Chloride (R-Cl) + SO2 ^ + HCl
- very efficient with primary and secondary alcohols d/t the main
byproduct (SO2) beig formed as a gas and leaving the reaction
mixture.
◉ Oxidation to Aldehydes, Ketones and CArboxylic Acids
Answer: Oxidation - increasing the oxygen content (number of
oxygen atoms) or the oxygen character (more bonds to oxygen)
-Primary Alcohols —> aldehydes —> Carboxylic Acids
-SEcondary Alcohols —>ketones
, -Tertiary - unreactive
◉ Jones Reagent
Answer: Cromium Triioxide with aqueous sulfuric acid —>
Chromic Acid
Disadvantage - strong oxidizer and wil not permit the synthesis of
aldehydes from primary alcohols
◉ Oxidizing agents that convert alcohols to Carbonyl compounds
Answer: Potassium Permanganate (KMnO4)
Sodium Hypochlorite (NaOCl)
◉ PCC Oxidation of Alcohols
Answer: Pyridinium Chlorochromate - oxidizes primary alcohols
to the aldehyde stage and stop there without further oxidation to
the Carboxylic acid.
-Dichloromethane (CH2Cl2) is typically the solvent used for PCC
oxidation o alcohols
◉ Ether
Answer: Alkyl or Aryl group that are covalently bonded to a single
O atom.
Generic Formula : R-O-R' (R groups can be the same - symmetric
or different - asymmetric)
WITH DETAILED QUESTIONS AND
RELIABLE ANSWERS
◉ Conversion using Phosphorous Halides (PX3)
Answer: X= Cl or Br
- Alcohol (3R-OH) + phosphorous trihalide (X2P-X) —> alkyl
halide (3R-X) + H3PO3
-particularly efficient as one molecule of PX3 can convert 3
molecules of alcohol to the corresponding alkyl halide
-byproduct of the reaction is phosphorous acid
◉ Conversion using Thionyl Chloride (SOCl2)
Answer: Alcohol (R-OH) + Thionyl Chloride (Cl-S=O-Cl) —> alkyl
Chloride (R-Cl) + SO2 ^ + HCl
- very efficient with primary and secondary alcohols d/t the main
byproduct (SO2) beig formed as a gas and leaving the reaction
mixture.
◉ Oxidation to Aldehydes, Ketones and CArboxylic Acids
Answer: Oxidation - increasing the oxygen content (number of
oxygen atoms) or the oxygen character (more bonds to oxygen)
-Primary Alcohols —> aldehydes —> Carboxylic Acids
-SEcondary Alcohols —>ketones
, -Tertiary - unreactive
◉ Jones Reagent
Answer: Cromium Triioxide with aqueous sulfuric acid —>
Chromic Acid
Disadvantage - strong oxidizer and wil not permit the synthesis of
aldehydes from primary alcohols
◉ Oxidizing agents that convert alcohols to Carbonyl compounds
Answer: Potassium Permanganate (KMnO4)
Sodium Hypochlorite (NaOCl)
◉ PCC Oxidation of Alcohols
Answer: Pyridinium Chlorochromate - oxidizes primary alcohols
to the aldehyde stage and stop there without further oxidation to
the Carboxylic acid.
-Dichloromethane (CH2Cl2) is typically the solvent used for PCC
oxidation o alcohols
◉ Ether
Answer: Alkyl or Aryl group that are covalently bonded to a single
O atom.
Generic Formula : R-O-R' (R groups can be the same - symmetric
or different - asymmetric)
