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Chem 219 Unit 5 Test with Questions Solved 100% Correct | Latest Update
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Chem 219 Unit 5 Test with Questions Solved100% Correct | Latest Update
What is the molecular formula for the reagent thionyl chloride? - ✔✔SOCL2
What does using Thionyl Chloride (SOCl2) for conversion of alcohols produce? Which
type of structures can this conversion using SOCl2 be used on? - ✔✔- used to
convert alcohols to the corresponding alkyl chloride.
- very efficient for primary and secondary alcohols.
What is the advantage of using Conversion via Thionyl Chloride? - ✔✔Although
there is no stoichiometric advantage in this reaction (like with PX3), the advantage to
this reaction is that the main byproduct (SO2) is formed as a gas and leaves the reaction
mixture.
Oxidation - ✔✔Oxidation is recognized in organic molecules by increasing the oxygen
content (the number of oxygen atoms) or the oxygen character (more bonds to oxygen).
What kind of alcohol structures can go through oxidation? - ✔✔primary
and secondary alcohols
,What are the products of oxidation of alcohols? - ✔✔Carbonyl
containing compounds: Aldehydes, Ketones, Carboxylic Acids
How does the oxidation of primary alcohols differ from the oxidation of secondary
alcohols? - ✔✔Primary alcohols are initially oxidized to aldehydes, which can then
be oxidized further to carboxylic acids.
Secondary alcohols are oxidized to ketones. No further oxidation (outside
of combustion, which destroys the molecule) is possible.
There are various chemical reagents that can accomplish the oxidation of alcohols to
carbonyl compounds. What are some chemical reagents for oxidation? -
✔✔chromic acid (H2CrO4)
potassium permanganate (KMnO4)
sodium hypochlorite (NaOCl)
Jones' Reagent - what is it? What are its disadvantages? - ✔✔The mixture of
chromium trioxide (CrO3) with aqueous sulfuric acid. Produces chromic acid (H2CrO4).
This is added to a solution of the alcohol dissolved in acetone as the solvent. Chromic
acid is a strong oxidizing agent and will oxidize primary alcohols to carboxylic acids
without stopping at the aldehyde stage. Secondary alcohols are oxidized to ketones.
One obvious disadvantage of using Jones' Reagent is that it is a strong oxidizer and
will not permit the synthesis of aldehydes from primary alcohols.
, What benefit is PCC (pyridinium chlorochromate) for oxidation reactions? - ✔✔PCC
will accomplish the oxidation for a primary alcohol to the aldehyde stage and stop
there without further oxidation to the carboxylic acid.
A disadvantage of using Jones' Reagent is that it is a strong oxidizer and will not permit
the synthesis of aldehydes from primary alcohols (it will continue to the carboxylic
acid stage). For this purpose, a mild oxidizing reagent known as PCC is used.
How do tertiary alcohols react during oxidation reactions? - ✔✔Tertiary alcohols
are unreactive in these types of oxidation reactions. Research into the mechanism of
these types of oxidations has revealed that the alcohol must have at least one
hydrogen attached to the carbon on the hydroxyl-bearing carbon.
ethers - ✔✔All ethers are organic molecules in which two alkyl or aryl (R) groups
are covalently bonded to a single oxygen atom. The generic formula for an ether is R-O
R'. The R groups can be the same (symmetric ether) or they can be different
(asymmetric ether).
Nomenclature of Ethers and Epoxides - ✔✔Go to Module 5.3
alkoxy substituent - ✔✔an -OR group attached to the parent chain
methoxy - ✔✔The name for a substituent attached to the parent chain of just O-CH3
Epoxides - ✔✔Three-membered cyclic ethers, composed of two carbon atoms and
a single oxygen.
Epoxides are also known as oxiranes. The small, three-membered ring of an epoxide is
very highly strained (severe angle strain), and as a result, epoxides are useful in
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