Download Organic Chemistry

Organic Chemistry
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Practice Exam Organic Chem
Read all questions before you start. Show all work and explain your answers to receive full credit. Report all numerical
answers to the proper number of significant figures. By signing your signature above you agree that you have worked alone and
neither give nor received help from any source. Keep your eyes on your own paper at all times
System
LENGTH:
VOLUME
MASS
Temperature
English:
1 ft = 12 in
1 gal = 4 qt
1 lb = 16 oz
T  F = 1.8T  C + 32
1 mile = 5280 ft
1 qt = 57.75 in3
1 ton = 2000 lb
1 yd = 3 ft
SI-
1 in = 2.54 cm
1 L = 1.057 qt
1 lb = 453.6 g
English:
1 mi = 1.609 km
1 qt = 0.946 L
1 oz = 28.35 g
1 mole = 6.02•1023
Misc. info
Group
Structural Feature
Alkane
single bond
Alkene
double bond
Alkyne
triple bond
Alcohol
-OH group
Ether
R-O-R
Aldehyde
RCHO
Ketone
R-CO-R
carboxylic acid
R-COOH
ester
RCOOR'
amine
R R'R"N
amide
R-CONHR'
Alkyl groups:
Methyl
Ethyl
Suffix
-ane
-ene
-yne
-ol
ether
-al
-one
-oic acid
-ate
-amine
-amide
T C =
(T  F − 32)
1.8
R = 8.314 J/ mol•K or .08206 L•atm/mol•K
.
#C
1
2
3
4
5
6
7
8
9
10
Reactivity
1
CnH2n
CnH2n-2
Alkane
methane
ethane
propane
butane
pentane
hexane
heptane
octane
nonane
decane
Alkene
Alkyne
ethene
propene
butene
pentene
hexene
heptene
octene
nonene
decene
ethyne
propyne
butyne
pentyne
hexyne
heptyne
octyne
nonyne
decyne
Alkene & Alkynes
Halogenation (+ X2)
Propyl
Butyl
n-prolyl
n-butyl
2
Hydrogenation (+ H2)
iso-propyl
iso-butyl
3
Hydrohalogenation (+ HX )
4
Polymerization
tert butyl
sec butyl
.
prefix
methethpropbutpenthexheptoctnondec-
CnH2n+2
Multiple -choice. Show work for partial credit.
1
2
3
4
5
6
7
The functional group of acetic acid is
a) Alcohol
b) aldehyde
c) carboxylic acid
d) ester
e) ester
The VSEPR structure of methane is
a) linear
b) trigonal
c) bent
d) tetrahedral
e) pyramid
A tertiary carbon is bonded directly to:
a) 2-hydrogens
b) 3 carbons
c) tert-carbons
d) 3-carbons
e) 4-carbons
d) pentyne
e) pentanol
What is the name of the organic compound with the formula C7H14.
a) pentene
b) heptene
c) heptyne
The bond angle between for H-C-H in methane is
a) 180°
b) 120°
c) 109.5°
d) 90°
e)not constant
Which is not an organic compounds
a) sodium hydroxide
b) octane
c) ethanol
d) toluene
e) glycol
Which of the following formulas is/are correct organic structures?
O
a)
H
c)
8
H
C H C
H
H
H
C
H
Cl
C
C
H
H
H C O
H
b)
H
C H
H
C
H
C
O
H
Which of the following is a correct IUPAC name.
a) 4-methylpentane
b) 4,4-dimethylhexane
d)
H
C
Br
H H
C C N H
Br H H
H
C
H
c) 3, 4-dimethylnonane
N H
H
d) 2-ethyl-3-methylhexane
9
10
The molecular formula for 5-butyl-2,4-dimethyldecane is
a) C15H32
b) C17H36
c) C14H30
Which of the following names is correct ?
a) 2-dimethylbutane
b) 3-methylhexane
c) 2-ethylpentane
Br
11
The name of the following structure is:
Br
F
H
C
H
C
Cl
C
H
a) 1-chloro-2,2-dibromo-1-fluoro-1-methylethane
c) 1,1-dibromo-2-chloro-2-fluoropropane
12
13
Ethyne is a(n)
a) alkane
15
e) C10H22
d) 2-methylcyclohexane
H
b) 3,3-diboromo-2-chloro-2-fluoropropane
d)1,1-dibromo-2,2 dichlorofluoropropane
c) alcohol
d) aromatic
e) alkyne
c) 5
d) 6
e) 7 or more
c) CnH2n-2
d) CnHn
e) CH5
How many alkyne isomers are possible with the molecular formula C6H10?
a) 3 or less
14
b) alkene
d) C16H34
b) 4
Alkanes have the general formula
a) CnH2n+2
b) CnH2n
Which of the following is an aromatic compound? (note: Hydrogens are omitted for clarity)
O
a)
16
O
b)
Pentane has the formula
a) C5H12
b) C5H10
c)
d)
c) C7H14
d) C7H16
e) C5H8
17
18
Which compound below is not an alcohol
a) ethylene glycol
b) calcium hydroxide
H3 C
Name the following molecule:
a) nonane
b) decane
c) phenol
20
What is the name for the following
a) 2-methyl-3-propylheptane
d) 4-isobutyloctane
e) vodka
d) octene
e) nonene
(CH2 ) 8 CH3
c) octane
H3 C
19
d) propanol
CH3
CH3
H3 C
b) 2,2-dimethylpropane
e) 4-isopropyloctane
The addition reaction between 2-pentene and hydrogen produces
a) 2-pentane
b) pentane
c) 2-pentyne
c) 2-methyl-3-butylhexane
d) cyclopentane
e) 2,3-dihydropentane
OH
21
22
23
24
The classification of the following molecule is:
a) alcohol
b) aldehyde
c) carboxylic acid
d) ether
e) butane
Which of the following functional groups does not contain a doubly-bonded oxygen
a) aldehyde
b) carboxylic acid
c) ester
d) ketone
What is the functional group for the compound
a) hydroxide
b) carboxylic acid
O
HC
e) ether
OH
c) amine
d) ketone
e) ester
How many implied hydrogens are there in the hydrocarbon molecule shown ?
This structure is drawn with out hydrogens attached:
C
C
a) 15
b) 9
c) 12
d) 16
C
C
C
e) 17
C
C
C
C
C
C
C
25
26
Which functional group(s) or class of organic compound(s) is not
present in compound shown:
a) amine
b) ester
c) alkene
d) hydroxyl
e) amide
O
C
H
C
H
C
H
C
O
O
CH 3
Correct Name
3-methylheptane
Correct name
1,2-dimethylcyclobutane
Correct name
as given above
(16 pts) Determine the total isomers that can be formed from 4 carbon atoms, 7 hydrogen atoms and one chlorine atom (1 pt for
each isomer). Draw stick forms for all isomers you have proposed. Label all chiral carbons in the isomers you have drawn with an
asterisk (*). Use the molecular modeling kit to assist you. For this question, points will be deducted for proposing identical
structures or stating a carbon is chiral if it is not.
t-1-chloro-1-butene
28
H3 C
NH 2
(16 pts) Draw the structure of each compound listed below.
Some of the compounds named below are correct and others are incorrect. Circle the names that are incorrect and explain why the
names are incorrect. Write the correct IUPAC names for those compounds that you circled.
i) 2-methyl-4-hexene
ii) 2-ethylhexane
iii) 1,4-dimethylcyclobutane
iv) 3-ethyl-3,4-dimethylheptane
Correct Name
5-methyl-2-hexene
27
HO
c-1-chloro-1-butene
4-chloro-1-butene
1-chloro trans -2-butene
2-chloro cis-2-butene
1-chloro-2-methyl-1-propene
1-chloro-1-methyl cyclopropane
cis 1-chloro-2-methyl
cyclopropane
2-chloro-1-butene
3-chloro-1-butene
2-chloro trans-2-butene
1-chloro cis-2-butene
3-chloro-2-methyl-1-propene
trans 1-chloro-2-methyl
cyclopropane
1-chloro cyclobutane