CHEM 219 Organic Chemistry
Comprehensive Questions and
Answers 2026/2027 Updated
1. cyclohexanecarbonitrile - ANSWER name this molecule
2. benzenecarbonitrile - ANSWER name this molecule
3. relatively high boiling points - ANSWER do nitriles have high or low
boiling points?
4. liquid - ANSWER what state are small nitriles in at room temps?
5. No- they lack a hydrogen directly attached to an electronegative element -
ANSWER do nitriles form hydrogen bonds?
6. polar
7. very electronegative - ANSWER are nitriles polar or non-polar?
8. strong permenent dipole-dipole attracts and van der waals dispersion forces -
ANSWER what type of strong attractions do nitriles have?
9. solubility decreases - ANSWER As the size of the alkyl groups attached to
the nitrile group increases, what happens to the solubility?
10.water and alcohol (H from these attaches to lone pair of N on nitrile) -
ANSWER what molecules can hydrogen bond to nitriles?
11.Sn2 reaction of cyanide ion with an unhindered primary or secondary alkyl
halide - ANSWER what is the most common preparation of nitriles?
12.nucleophilic attack (d/t the resonance structure causing an eletrophile
carbon) - ANSWER what are carbons in nitriles susceptible to?
13.imine - ANSWER what is the intermediate form of nitrile?
14.carboxylic acids - ANSWER what does the hydrolysis of nitriles create?
,15.carboxylic acid and ammonium ion - ANSWER nitrile +water + acid =
16.carboxylate salt + ammonia
17.if acid is then added =
18.carboxylic acid is formed - ANSWER nitrile + water + base =
19.Grignard reagent - ANSWER An alkyl magnesium halide used to make
carbon-carbon bonds. Alkyl group in a Grignard reagent has a negative
charge and acts as a nucleophile attacking electrophilic carbons.
20.react alkyl halide (typically bromide) with magnesium metal in an inert
solvent (diethyl ether or pentane) under anhydrous (no water) conditions -
ANSWER how is a Grignard reagent made?
21.negative charge on carbon - ANSWER what type of charge is caused by the
mag ion in Grignard reagent?
22.nucleophile - ANSWER Are grignard reagents nucleophiles or
electrophiles?
23.base - ANSWER are grignard reagents acids or bases?
24.-intermediate imine forms then is hydrolyzed with acid to yield KETONES -
ANSWER what happens with grignard reagents are reacted with nitriles?
25.2 ways - ANSWER how many ways can a ketone be prepared by nitrile
+grignard reagent?
26.amine - ANSWER derivative of ammonia where one or more hydrogen
replaced by carbon-based groups
27.primary amine - ANSWER R-NH2
28.secondary amine - ANSWER R2NH
29.tertiary amine - ANSWER R3N
30.Ammonia - ANSWER NH3
, 31.quarternary amine - ANSWER a configuration in which nitrogen has four
bonds with other atoms and, as such, the molecule has an electron deficit
32.name by alkyl group +amine at the end - ANSWER naming simple amines
33.Ethylamine - ANSWER
34.diethylamine - ANSWER
35.triethylamine - ANSWER
36.cyclohexylamine - ANSWER
37.name parent chain and then name amine as amino substituent - ANSWER
naming amines with additional functional groups present
38.3-aminobutanoic acid - ANSWER
39.2,4-diaminobenzoic acid - ANSWER
40.1,4-diaminobutane - ANSWER
41.4-amino-2-butanone - ANSWER
42.name amine as N-substituted where largest compound = parent
43.name other groups as N-alkyl substituents - ANSWER naming
unsymmetrically substituted 2nd and 3rd degree amines
44.N-ethyl-N-methylpropylamine - ANSWER
45.N,N-dimethylpropylamine - ANSWER
46.N-ethyl-N-methyl-cyclohexylamine - ANSWER
47.amino groups direct attached to aromatic ring - ANSWER aryl amine
naming
48.aninline/ aminobenzene - ANSWER
49.benzylamine - ANSWER
Comprehensive Questions and
Answers 2026/2027 Updated
1. cyclohexanecarbonitrile - ANSWER name this molecule
2. benzenecarbonitrile - ANSWER name this molecule
3. relatively high boiling points - ANSWER do nitriles have high or low
boiling points?
4. liquid - ANSWER what state are small nitriles in at room temps?
5. No- they lack a hydrogen directly attached to an electronegative element -
ANSWER do nitriles form hydrogen bonds?
6. polar
7. very electronegative - ANSWER are nitriles polar or non-polar?
8. strong permenent dipole-dipole attracts and van der waals dispersion forces -
ANSWER what type of strong attractions do nitriles have?
9. solubility decreases - ANSWER As the size of the alkyl groups attached to
the nitrile group increases, what happens to the solubility?
10.water and alcohol (H from these attaches to lone pair of N on nitrile) -
ANSWER what molecules can hydrogen bond to nitriles?
11.Sn2 reaction of cyanide ion with an unhindered primary or secondary alkyl
halide - ANSWER what is the most common preparation of nitriles?
12.nucleophilic attack (d/t the resonance structure causing an eletrophile
carbon) - ANSWER what are carbons in nitriles susceptible to?
13.imine - ANSWER what is the intermediate form of nitrile?
14.carboxylic acids - ANSWER what does the hydrolysis of nitriles create?
,15.carboxylic acid and ammonium ion - ANSWER nitrile +water + acid =
16.carboxylate salt + ammonia
17.if acid is then added =
18.carboxylic acid is formed - ANSWER nitrile + water + base =
19.Grignard reagent - ANSWER An alkyl magnesium halide used to make
carbon-carbon bonds. Alkyl group in a Grignard reagent has a negative
charge and acts as a nucleophile attacking electrophilic carbons.
20.react alkyl halide (typically bromide) with magnesium metal in an inert
solvent (diethyl ether or pentane) under anhydrous (no water) conditions -
ANSWER how is a Grignard reagent made?
21.negative charge on carbon - ANSWER what type of charge is caused by the
mag ion in Grignard reagent?
22.nucleophile - ANSWER Are grignard reagents nucleophiles or
electrophiles?
23.base - ANSWER are grignard reagents acids or bases?
24.-intermediate imine forms then is hydrolyzed with acid to yield KETONES -
ANSWER what happens with grignard reagents are reacted with nitriles?
25.2 ways - ANSWER how many ways can a ketone be prepared by nitrile
+grignard reagent?
26.amine - ANSWER derivative of ammonia where one or more hydrogen
replaced by carbon-based groups
27.primary amine - ANSWER R-NH2
28.secondary amine - ANSWER R2NH
29.tertiary amine - ANSWER R3N
30.Ammonia - ANSWER NH3
, 31.quarternary amine - ANSWER a configuration in which nitrogen has four
bonds with other atoms and, as such, the molecule has an electron deficit
32.name by alkyl group +amine at the end - ANSWER naming simple amines
33.Ethylamine - ANSWER
34.diethylamine - ANSWER
35.triethylamine - ANSWER
36.cyclohexylamine - ANSWER
37.name parent chain and then name amine as amino substituent - ANSWER
naming amines with additional functional groups present
38.3-aminobutanoic acid - ANSWER
39.2,4-diaminobenzoic acid - ANSWER
40.1,4-diaminobutane - ANSWER
41.4-amino-2-butanone - ANSWER
42.name amine as N-substituted where largest compound = parent
43.name other groups as N-alkyl substituents - ANSWER naming
unsymmetrically substituted 2nd and 3rd degree amines
44.N-ethyl-N-methylpropylamine - ANSWER
45.N,N-dimethylpropylamine - ANSWER
46.N-ethyl-N-methyl-cyclohexylamine - ANSWER
47.amino groups direct attached to aromatic ring - ANSWER aryl amine
naming
48.aninline/ aminobenzene - ANSWER
49.benzylamine - ANSWER
