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

Alcohol and Phenol Derivatives

• with 3,5-dinitrobenzoyl chloride

• 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

• Classification tests

• Derivatives

• Spectra

Similarly: naphthyl urethanes

Alcohols

IR:

H-NMR:

Exchange with D2O

• Preliminary tests

• Solubility

• Classification tests

• Derivatives

• Spectra

OH in gas phase ….??

H-bonded!

Phenols

H-NMR

IR

Unknown 2

• Carboxylic Acids• Anhydrides

• Esters• Amides

• Amines• Nitro

Functional groups of the above?

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?

Solubility Tests

Carboxylic Acids Anhydrides Esters Amides Amines Nitro

• Preliminary tests

• Solubility?

• Classification tests

• Derivatives

• Spectra

Preliminary test results?

Mp., bp.,

odor,

color…

• Preliminary tests?

• Solubility

• Classification tests

• Derivatives

• Spectra

Carboxylic Acids Anhydrides Esters Amides Amines Nitro

Carboxylic AcidsGood mp.s (consider recrystallization)

Neutralization Equivalent (titration) experimental instructions on our webpage

• Solubility

• Classification tests

• Derivatives (not done)

• Spectra

Derivatives (we do not do them in the lab):

Convert carboxylic acid into acid chloride first, then into amides

RCO2H + NaOH        RCO2(–) Na(+)

aq.   +   H2O

1.

2.

+ HCl

Esters

Classification Test

Deep-red to purple

• Preliminary tests?

• Solubility

• Classification tests

• Derivatives

• Spectra

Compare with known ester!

a hydroxamic acid

Derivatives for Esters

Hydrolyze (experimental instructions on our webpage)

… to its carboxylic acid component (mp.)

…. and its alcohol component alcohol derivative

• Preliminary tests?

• Solubility

• Classification tests

• Derivatives

• Spectra

Amines

Derivatives

Picrates

Benzamides: amine + benzoyl chloride

NH 2

OH

NO 2

NO 2

O 2 N

+

• Preliminary tests?

• Solubility

• Classification tests

• Derivatives

• Spectra

Carboxylic Acids

IR:

H-NMR:

• Preliminary tests?

• Solubility

• Classification tests

• Derivatives

• Spectra

OH in gas phase(non-H-bonded)

Amines

IR:

H-NMR:

Voodoo Lily

Amides

H-NMR:

• Preliminary tests?

• Solubility

• Classification tests

• Derivatives

• SpectraIR?

Nitro Compounds Typical properties?

Classification test:

Always do with a known compound to compare!

Derivatives:

Reduce to amine and then prepare amine derivatives

• Preliminary tests?

• Solubility

• Classification tests

• Derivatives

• Spectra

Iron (II) Hydroxide Test for Nitro GroupsNitro Compounds                                                                                                                                                                               

• IR(your take home miniquiz is due…)

• Inert Compounds:

AlkanesAromatic Hydrocarbons

Alkyl halides

Next time (11/4):