Transcript F08C336_10Unknown 3

How to be, become, stay successful in this class
(i.e. get a good grade!!)
• Attend every class (including lab lecture!)
• Preview/review and study lectures. Do Practice
questions and problems on sample exams
• See your teacher when problems come up
• Study well for quizzes/exams, and start studying
early
For a Midterm grade see your lab instructor
Questions, Problems
re. Unknown 1?
Today:
Unknown 1 (conclusion)
Unknown 2
• Preliminary tests
Alcohol and Phenol Derivatives
• Solubility
• Classification tests
• Derivatives
• with 3,5-dinitrobenzoyl chloride
• Spectra
• urethanes
Similarly: naphthyl urethanes
→Take Home Miniquiz (2 pts.): Write a mechanism
for the formation of the phenylurethane of 1-butanol
Due by next lab lecture (late ones not accepted…)
• Preliminary tests
• Solubility
Alcohols
• Classification tests
• Derivatives
• Spectra
IR:
H-bonded!
OH in gas
phase ….??
H-NMR:
Exchange with
D2O
Phenols
IR
H-NMR
Unknown 2
• Carboxylic Acids
• Anhydrides
• Esters
• Amides
• Amines
• Nitro
Functional groups of the above?
Carboxylic Acids
Anhydrides
Esters
Amides
Amines
Nitro
• Preliminary tests
• Solubility?
• Classification tests
Solubility Tests
• Derivatives
• Spectra
What type of information do you get if your unknown
1. is soluble in water?
2. is soluble in NaOH and in NaHCO3?
3. is soluble in NaOH only, not in NaHCO3?
4. is soluble in dilute HCl solution?
5. is soluble only in conc H2SO4?
6. is not soluble in any of the above solvents?
• Preliminary tests?
Carboxylic Acids
Anhydrides
Esters
Amides
Amines
Nitro
• Solubility
• Classification tests
• Derivatives
• Spectra
Preliminary test results?
Mp., bp.,
odor,
color…
• Solubility
Carboxylic Acids
• Classification tests
Good mp.s (consider recrystallization)
• Derivatives (not done)
• Spectra
Neutralization Equivalent (titration)
experimental instructions on our webpage
RCO2H + NaOH
RCO2(–) Na(+)aq. + H2O
Derivatives (we do not do them in the lab):
Convert carboxylic acid into acid chloride first, then into amides
1.
+ HCl
2.
• Preliminary tests?
Esters
• Solubility
• Classification tests
Classification Test
• Derivatives
• Spectra
a hydroxamic
acid
Deep-red
to purple
Compare with known ester!
Derivatives for Esters
Hydrolyze (experimental instructions on our
webpage)
• Preliminary tests?
• Solubility
… to its carboxylic acid component (mp.)
• Classification tests
• Derivatives
• Spectra
…. and its alcohol component
alcohol derivative
• Preliminary tests?
• Solubility
Amines
• Classification tests
Derivatives
• Derivatives
• Spectra
Picrates
OH
NH
O 2N
2
NO
2
+
NO
2
Benzamides: amine + benzoyl chloride
Carboxylic Acids
• Preliminary tests?
• Solubility
IR:
• Classification tests
• Derivatives
• Spectra
OH in gas phase
(non-H-bonded)
H-NMR:
Amines
IR:
Voodoo Lily
H-NMR:
Amides
• Preliminary tests?
• Solubility
• Classification tests
IR?
H-NMR:
• Derivatives
• Spectra
• Preliminary tests?
Nitro Compounds
Typical properties?
Classification test:
• Solubility
• Classification tests
• Derivatives
• Spectra
Iron (II) Hydroxide Test for Nitro Groups
Nitro Compounds
Always do with a known compound to compare!
Derivatives:
Reduce to amine and then prepare amine derivatives
Next time (11/4):
• Inert Compounds:
Alkanes
Aromatic Hydrocarbons
Alkyl halides
• IR
(your take home miniquiz is due…)