Regents Review 1
Organic Chemistry
Notes
1. All organic compounds must contain the element
(1) phosphorus
(3) carbon
(2) oxygen
(4) nitrogen
2. In saturated hydrocarbons, carbon atoms are bonded to each other by
(1) single covalent bonds, only
(2) double covalent bonds, only
(3) alternating single and double covalent bonds
(4) alternating double and triple covalent bonds
3. Which compound is a saturated hydrocarbon?
(1) hexane
(3) hexanol
(2) hexene
(4) hexanal
4. Which compound has an isomer?
-H
( 1 )
(3) H—C-C-C-H
( I i
I
H
( 2 ) H-C-C-H
I f
H H
H
H H
H
H H H
(4) H-C-C—C-C-H
I I I I
H H H H
5. Which structural formula represents 2-pentyne?
V V
H— C— C— C—C— H
H
H
_
H
f»__„ LJ
v*
n
I J _ f~* _ f*— f~*
rf
*~* _ I*
LJ
O
O — Lr ^~w — L* — M
H
H
H H
(3)
H—C—H
H I H
p r " 't\
u
~~^\j—~\j
H—C—H
H
(2)
H
H
H H
I
I I
H—C— C s=C - C — C—H
H
H H
(4)
6. Which formula correctly represents the product of an addition reaction
between ethene and chlorine?
(1)CH2CI2
(3)C2H4d2
(2)CH3C1
(4)C2H 3 C1
Regents Review
7. The empirical formula of a compound is CH 2. Which molecular formula is
correctly paired with a structural formula for this compound?
H—C—Y— H
(t)
H
(2)
C2H4
H
H-C=C-H
H
H
(3)
H H H
—
r— I— f
C3H8 H—C—C— C — H
(4)
C3H8
A A A
i1 r r
H-C=C-C-H
H
H
H
8. The functional group —COOH is found iin
(1) esters
(3) alcohols
(2) aldehydes
(4) organic acids
9. What is the IUPAC name of the compound with the following structural
formula?
H O H H
I I! I I
H-C-C-C-C-H
I
I I
H
H H
(l)propanone
(2) propanal
(3) butanone
(4) butanal
10. What is the total number of electron pairs that are shared between the two
carbon atoms in molecule of ethyne?
(1)1
(2)2
(3)3
(4)4
11. Which pair of compounds are isomers?
(l)NO2andN2O4
(2)P2O5andP4Oio
(3) HCOOH and CH 3 COOH
(4)CH3OCH3andCaH50H
12. Hexane (C e H H ) and water do not form a solution. Which statement
explains this phenomenon?
(1) Hexane is polar and water is nonpolar.
(2) Hexane is ionic and water is polar.
(3) Hexane is nonpolar and water is polar.
(4) Hexane is nonpolar and water is ionic.
2
Regents Review
13. Which organic compound is unsaturated?
(1) 2-methylbutane
(3) 2-hexanol
(2) 2-chloropropane
(4) 2-pentene
14. Which compound is an isomer of pentane?
(1) butane
(3) methyl butane
(2) propane
(4) methyl propane
15. Which structural formula is incorrect'?
f
H—C—Cl
_...
O
I
H—C—OH
H
(1)
(3)
H
\C
H/
H
»\j_r_
H/°
\
M
?
H
?
H
(4)
(2)
16. Which structural formula represents an ether?
H O
I II
H—C-C-H
H
H H
I
I
H-C-C-OH
I
I
H H
(1)
(3)
H O
I II
H-C-C-OH
I
H
H
H
I
H-C-O-C-H
I
I
H
H
(2)
(4)
17. Which structural formula correctly represents a hydrocarbon molecule?
H
C-C
H
H
d)
H
H
H-C-C,
O
H
(3)
H
H,
,H
C=C
s
H
H
(2)
H
(4)
18. The process of joining many small molecules into larger molecules is called
(1) neutralization
(3) saponification
(2) polymerization
(4) substitution
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Regents Review 4
19. Which formula is an isomer of butane?
H
H
H
I
I
I
C — C — C — C—H
I Hi Hi HI
H
H
H
H
I
I
I
H— C — C — C — H
l Hi Ht
H
(1)
O)
H
H— C —H
H
I
I
.
H— C— C—
I
H
H
H
|_
H
C —H
I
H
H— C— H
H
H
I
T
h
H— C — C — C — H
I
T
I
H
I
H
H— C — H
I
H
( 4)
(2)
20. Which pair of compounds are alcohols?
H
H
H
—H
(D
H
OH
H
H
H
(3)
1—1
F1
ztr^fi
dllU
H
H
H-A-/
i
OH
O
c—c
HO^
II
n
I I
H—C—c~-c —OH
H
1
O
, ~,
ij
n
L»
^*
/"*
(2) H
H-C\j
\j
1
and
I
and
VOH
rvi
H-C-rr-H
H
and
XH
OH H
V
H— c— c
VOH
21. Which type of reaction is represented by the equation below?
Note: PI and n are very large numbers equal to about 2000.
H.
n
"C ~
H
(1) esterification
(2) fermentation
(3) saponification
(4) polymerization
Regents Review 5
22. Given the formulas of four organic compounds:
H H O
l l »
( a ) H-C-C-C-H
H O H
( H I
(C) H—C-C-C-H
H H
H
H
H H O
I I II
< b ) H-C-C-C-OH
H-C-C-C-H
H H
H OHH
H H H
Which pair below contains an alcohol and an acid?
(1) a and b
(3) b and d
(2) a and c
(4) c and d
23. Which 0.1 M solution contains an electrolyte?
(l)C6Hi2O6(aq)
(3)CH3OH(aq)
(2) CH 3 COOH(aq)
(4) CH 3 OCH 3 (aq)
24. Which of these compounds has chemical properties most similar to the
chemical properties of ethanoic acid?
(1)C3H?COOH
(3)C2HsCOOC2H5
(2)C2HsOH
(4)C2HsOC2H5
25. Given the reaction:
O
II
O
II
CH3C~OH + HOC2HS
CH3C~O—C2H5 + H2O
This reaction is an example of
(1) fermentation
(3) hydrogenation
(2) saponification
(4) esterification
26. Which compound is an alcohol?
(1) propanal
(3) butane
(2) ethyne
(4) methanol
27. Which structural formula represents an alcohol?
H
O
H
H—C— C— C—H
I
I
•H
H
H
H
•C — C
VH
H
(3)
H
I
1
H — C ~i
1
H
H
II
t
1
1
1
C —C — OH
i
i
1
1
H
H
(2)
H
,O
H— C — C
I
V
OH
H
4)
Regents Review
28. In which reaction is soap a product?
(1) addition
(3) saponification
(2) substitution
(4) polymerization
29. Given the structural formulas for two organic compounds:
H H H O
i
l
f
H
11
H-C-C-C-C-OH
l i t
H H H
and
, i
I
H
n
O
H
i
H-C-C-C-O-C-H
i
l
l
H H
H
The differences in their physical and chemical properties are primarily due to
their different
( 1 ) number of carbon atoms__________________(3) molecular masses
_
(2) number of hydrogen atoms
(4) functional groups
30. What is the IUPAC name of the compound with the structural formula
shown below?
H H H
H
I I I
I
H-C-C-C=C-C-H
I I
I I
H H
H H
(1) 2-pentene
(2) 3-pentene
(3) 2-pentyne
(4) 3-pentyne
3 1 . Given the three organic structural formulas shown below:
H O H
I I I
H— C— C — C— H
• A
A
H O
I
II
H— C—C— OH
i
H Q H H
I I I
H— C— C— C— H
AH
Which organic- compound classes are represented by these structural formulas,
as shown from left to right?
(1) ester, organic acid, ketone
(2) ester, aldehyde, organic acid
(3) ketone, aldehyde, alcohol
(4) ketone, organic acid, alcohol
32. Given the equation:
Which molecule is represented by X?
(l)CaH4
(3)C 3 H6
(2)C2H6
(4)C3Hs
33. In the space provided in your answer booklet, draw the structural formula for butanoic acid. [1]
34. How is the bonding between carbon atoms different in unsaturated hydrocarbons and saturated
hydrocarbons? [1]
6
Regents Review
Base your answers to questions 35 through 37 on-ihe information below.
.,....,
Many artificial flavorings are prepared using the type of organic reaction shown below.
H O
I II
H-C-C-OH
I
H
Reactant 1
H H H
H O H H H
I I I
I II
l i t
+ HO-C-C-C-H —> H-C-C-O-C-C-C-H + HOH
I I I
I
I I I
HHH
H
HHH
Reactant 2
35. What is the name of this organic reaction? [1]
36. To what class of organic compounds does reactant 2 belong? [1]
37. In the space provided in your answer booklet, draw the structural formula of an isomer of
reactant 2. [I]
Base your answers to questions 38 and 39 on the condensed structural formula below.
CH 3 CH 2 CHCH 2
38. In the space provided in your answer booklet, draw the structural formula for this compound. [1]
39. The formula below represents a product formed when HC1 reacts withCH 3 CH 2 CHCH 2
H H H H
I
I
I I
H-C-C-C-C-H
I
I
I I
H Cl H H
What is an TUPAC name for this product? [1]
40. Given the ester: ethyl butanoate
a. In the space provided in your answer booklet, draw the structural formula for this ester. [1]
b. Determine the gram formula mass of this ester. [ 1 ]
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Regents Review
8
Diethyl ether is widely used as a solvent.
41. In the space provided in your answer booklet, draw the structural formula for diethyl ether. [1]
42. In the space provided in your answer booklet, draw the structural formula for an alcohol that is
an isomer of diethyl ether. [1]
Base your answers to questions 43 through 45 on the information below.
Ethene (common name ethylene) is a commercially important organic compound. Millions of
tons of ethene are produced by the chemical industry each year. Ethene is used in the manufacture of
synthetic fibers for carpeting and clothing, and it is widely used in making polyethylene. Lowdensity polyethylene can be stretched into a clear, thin film that is used for wrapping food products
and consumer goods. High-density polyethylene is molded into bottles for milk and other liquids.
Ethene can also be oxidized to produce ethylene glycol, which is used in antifreeze for automobiles.
The structural formula for ethylene glycol is:
H H
I I
H-C-C-H
OH OH
At standard atmospheric pressure, the boiling point of ethylene glycol is 198°C,
compared to ethene that boils at -104°C.
-..>-.-43. Identify the type of organic reaction by which ethene (ethylene) is made into poly-ethylene. [1]
44. According to the information in the reading passage, state two consumer products manufactured
from ethene. [1]
45. Explain, in terms of bonding, why ethene is an unsaturated hydrocarbon. [1]
46. Given the structural formula for butane:
H — C — C— C— C— H
I
I
I I
H H H H
In the space provided in your answer booklet,
draw the structural formula of an isomer of butane. [ 1 ]