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N b. piperidine
NH2 2. Give an acceptable name for each of the following compounds. N CH3
4
CH3 N,N-dimethylbenzylamine
N Cl-
tetrabutylammonium chloide
4. Circle the stronger base in the pair below, and briefly explain your choice.
NH2
NH2
The lone pair of electrons on the nitrogen in aniline are delocalized into the aromatic ring, which reduced the ability of aniline to donate electron (be a base). 5. Provide a detailed, stepwise mechanism for the reaction of acetyl chloride with n-propylamine.
O CH3 C Cl + H2NCH2CH2CH3 O CH3 C Cl H N CH2CH2CH3 H O CH3 C H + Cl H N CH2CH2CH3
6. Complete the following reaction sequences. a. 1) Ag2O 2) heat N CH3 CH3 3) CH3I 4) Ag2O 5) heat
d. CH H 3
e. O2N Br
f.
H NH2
g.
O CN
h. + HBr N N H
+ Br
l. Give an efficient method for preparing ethylisopropylamine from ethylamine. acetone / H lose of water 1) LAH 2) pH adjust H N
NH2
m. Devise an efficient method for preparing only 1-pentanamine from 1-chloropentane. Cl xs NH3 NH2
n. Complete the short synthesis below by providing the necessary reagents. NH2 1) NaNO2 / HCl 2) CuCN 3) LAH NH2
7. Circle the following amines that could be formed by reduction of an amide? 1) benzylamine 2) isopropylamine 3) aniline 4) triethylamine The answer is #1 and #4. 8. Provide a detailed, stepwise mechanism for the acid-catalyzed condensation reaction between benzaldehyde and methylamine.
O H
+
O H
H H2NCH3 H
H NHCH3 H
Base
CH3 N H
H NHCH3 H
H NHCH3
Base
N CH3
9. Circle the most basic compound in each of the following pairs. O NH2 A. or NH2 B. H N or O
The answer is A and B. 10. Propose a synthetic route to prepare p-nitroaniline from aniline.
NH2 NH2
NO2
11. A compound with the formula C11H16N2 gave the following IR and 1H NMR spectra. The proton at 1.6 ppm disappears on shaking with D2O. Propose a structure for the compound and show how your structure accounts for the observed spectra data.
5H
2H 4H 4H 1H
5 aromatic hydrogens (mono substituted benzene). Isolated CH2 at 3.5 ppm attached to aromatic ring and nitrogen. Peak @ 1.6 ppm is a N-H, since there is only one hydrogen this is a 2 amine. The other nitrogen must be a 3 amine. The peaks at 2.4 and 2.8 ppm indicate symmetrical ethylene groups CH2CH2-.
CH2 N
NH