Chemistry Reference
In-Depth Information
Learning Objectives
1.
Know the meaning of: aldehyde, ketone, carbonyl group, formaldehyde,
acetaldehyde, benzaldehyde, acetone, salicylaldehyde, acetophenone,
benzophenone, carbaldehyde group.
2.
Know the meaning of: nucleophilic addition, hemiacetal and acetal, aldehyde
hydrate, cyanohydrin.
3.
Know the meaning of: imine, hydroxylamine, oxime, hydrazine, hydrazone,
phenylhydrazine, phenylhydrazone, semicarbazone.
4.
Know the meaning of: lithium aluminum hydride, sodium borohydride, Tollens'
reagent, silver mirror test.
5.
Know the meaning of: keto form, enol form, tautomers, tautomerism, enolate anion,
α
-hydrogen and
α
-carbon, aldol condensation, mixed aldol condensation.
6.
Given the structure of an aldehyde or ketone, state its IUPAC name.
7.
Given the IUPAC name of an aldehyde or ketone, write its structure.
8.
Write the resonance contributors to the carbonyl group.
9.
Given the structure or name of an aldehyde or ketone, write an equation for its
reaction with the following nucleophiles: alcohol, cyanide ion, Grignard reagent or
acetylide, hydroxylamine, hydrazine, phenylhydrazine, 2,4-dinitrophenylhydrazine,
primary amine, lithium aluminum hydride, and sodium borohydride.
10.
Explain the mechanism of acid catalysis of nucleophilic additions to the carbonyl
group.
11.
Write the steps in the mechanism of acetal formation and hydrolysis. Draw the
structures of resonance contributors to intermediates in the mechanism.
12.
Given a carbonyl compound and a Grignard reagent, write the structure of the
alcohol that is formed when they react.
13.
Given the structure of a primary, secondary, or tertiary alcohol, deduce what
combination of aldehyde or ketone and Grignard reagent can be used for its
synthesis.
14.
Given the structure of an aldehyde or ketone, write the formula of the alcohol that is
obtained from it by reduction.
15.
Given the structure of an aldehyde, write the structure of the acid that is formed from
it by oxidation.
16.
Know which tests can distinguish an aldehyde from a ketone.
17.
Given the structure of an aldehyde or ketone, write the structure of the
corresponding enol and enolate anion.
18.
Identify the
α
-hydrogens in an aldehyde or ketone, and be able to recognize that
these hydrogens can be exchanged readily for deuterium.
19.
Write the structure of the aldol product formed by the self-condensation of an
aldehyde of given structure.
