Download Practice Problems for Exam 2

Practice Problems for Exam 2
CHEM 1407 and 1408
1. What are the general formulas for:
a) alcohol
b) ether
d) 2 amine
e) ketone
g) aldehyde
h) aromatic amine
c) phenol
f) 1 amine
i) hemiacetal
2. Complete the following general chemical equations by writing the name of all the expected products. If
no reaction occurs, write no reaction.
[O]
a) aldehyde ----------> ?
cat
b) 1 amine + carboxylic acid --------> ?
c) phenol + base ------> ?
d) 1 amine + HCl ------> ?
e) ether + KMnO4 --------> ?
NaBH4
f) aldehyde --------------> ?
g) ketone
NaBH4
--------------> ?
[O]
h) 1o alcohol -------> ?
[O]
i) 2o alcohol --------> ?
[O]
j) 3 alcohol -------> ?
o
cat
k) 3 amine + carboxylic acid ------> ?
l) ketone
[O]
---------> ?
m) Ketone or aldehyde + excess alcohol
H+
-----> ?
3. List any three different physical properties of aldehydes.
H+
-----> ?
2
4. Draw the structure of the following molecules:
a) N-Isopropyl-2-methylpentanamine
b) 3,3-Dimethyl-2-butanol
c) sec-Butyl ethyl ether
d) 3,3-Dimethylbutanal
e) 4-Ethyl-2-heptanone
f) Aniline
g) Ethyl dimethyl amine
5. Are the following 1 , 2 , 3 , or 4 amines? Is hydrogen bonding possible between these amines and an
identical molecule?
CH3N(CH3)2 CH3CH2NHCH2CH3
(a)
(b)
(c)
(d)
6. What organic families do each of the following belong?
(1) hydroxyl group
(2) carbonyl group
(3) alkoxy group
7. Put the following compounds in order from highest to lowest boiling point.
Propane
butane
ethyl methyl ether
1-propanol
dimethylamine
dimethyl ketone
8. Compound Z contains a carbonyl functional group. With addition of the Benedict's reagent to Z, the
solution is blue. What s your conclusion about Z?
9. What intermolecular forces occur within the following organic families?
a) alkanes
b) alkenes
c) 1 amine d) ethers
e) alkynes
f) aldehydes
g) ketones
h) phenols
i) alcohols
j) 3 amine
10. Compound A contains a carbonyl group and produces a silver mirror with Tollens reagent. What can
you conclude about compound A?
3
11. Complete and balance the following reactions. If no reaction occurs, write N.R. and explain. ( =
benzene ring.
a)
+
O
b) (CH3)2CHCH
NaOH
—> ?
NaBH4
--------------> ?
[O]
c) CH3CH2CH2OH --------> ?
[O]
---------> ?
d)
e)
O
CH3CCH2CH2CH3
NaBH4
-------------> ?
[O]
f) (CH3)2CHCHO ----------> ?
[O]
g) CH3OCH2CH3 ----------> ?
[O]
h) CH3CH2COCH3 ----------> ?
i) CH3CH2NHCH2CH3
j) 2 –OH
+
+ HCl
=O
-----> ?
H+
<----------> ?
cat
k) (CH3)3N + CH3COOH ------> ?
4
l) CH3CH=CH2
H+
+ H2O ------> ?
[O]
m) (CH3)3COH --------> ?
12. Give the IUPAC name for the following molecules.
CH3
a)
(CH3)3CCHCHCHO
CH3
b)
CH3CHCOCHCH3
CH3
Also, what is its common name?
CH3
c)
(CH3)2CHNHCH3
d)
CH3NCH2CH2CH2CH3
CH2CH2CH3
e)
(CH3)2CHOCH2CH3
OH
f)
(CH3)2CHCH2CH2CHCH3
13. Classify the following as primary, secondary, tertiary alcohols or phenols?
a) ethanol
b) 2-methyl-2-propanol
CH3
c) CH3CHCH2OH
OH
d) CH3CH2C(CH3)2
5
ANSWERS:
1. (Ph = phenyl group, benzene ring)
a) ROH
b) ROR or ROR
d) R2NH or RNHR
e)
O
O
or
g) O
RCR RCR
c) PhOH
f) RNH2
RCH
i)
h) PhNH2
OH
R2COR (same or different R)
2. a) carboxylic acid
b) amide + H2O
c) phenoxide ion + anion + H2O
d) alkyl ammonium chloride salt
e) no reaction
f) primary alcohol
g) 2 alcohol
h) [aldehyde] —> carboxylic acid
i) ketone
j) no reaction
k) no reaction
l) no reaction
m) hemiacetal —> acetal
3. polar molecule; dipole-dipole interactions within the family; moderate melting points and boiling points;
water soluble with 5 carbons are less due to hydrogen bonding between aldehydes and water
4. a) (CH3)2CHNHCH2CHCH2CH2CH3
OH
CH3
b) CH3CHC(CH3)3
c) CH3CH2CHCH3
OCH2CH3
d) (CH3)3CCH2CHO
CH2CH3
e) CH3CH2CH2CHCH2CCH3
O
f)
g) CH3CH2N(CH3)2
6
5. a) 3 ; no
b) 2 ; yes
6. (1) alcohols and phenols
c) 2 ; yes
d) 1 ; yes
(2) ketones and aldehydes
(3) ethers
7. 1-propanol > dimethylamine > ( ethyl methyl ether, dimethyl ketone) > butane > propane
8. Compound Z must be a ketone.
9. a) London force b) London forces
e) London forces
f) dipole-dipole forces
i) Hydrogen bonding j) dipole-dipole forces
10. Compound A is an aldehyde.
11. ( = benzene ring)
a)
+ H2O + Na+
b) (CH3)2CHCH2OH
c) CH3CH2CO2H
d)
e)
OH
CH3CHCH2CH2CH3
f) (CH3)2CHCO2H
g) No reaction
h) No reaction
+
i) CH3CH2NH2CH2CH3 + ClO
j)
O
c) Hydrogen bonding
g) dipole-dipole forces
d) dipole-dipole forces
h) Hydrogen bonding
7
k) No reaction
OH
l) CH3CHCH3
m) No reaction
12. a) 2,3,4,4-Tetramethylpentanal
b) 2,4-Dimethyl-3-pentanone (IUPAC);
Diisopropyl ketone (common name)
c) Isopropyl methyl amine or 1, N-Dimethylethanamine
d) N-Methyl-N-propylbutanamine
e) Ethyl isopropyl ether
f) 5-Methyl-2-hexanol
13. a) 1
b) 3
c) 1
d) 3