
Organic
Chemistry
 Alkane- hydrocarbon that contains only
single bonds.
 Why are alkanes the simplest and least
reactive class of organic compounds?
Because they contain only hydrogen
and spy hybridized carbon and have no
reactive functional groups
 Heteroatoms- Atoms other than carbon
or hydrogen
 Alkanes act poorly as what properties?
acids/bases, electrophiles, and
nucleophiles.
 Homologous series- a series of
compounds that differ only by the
number of CH2 groups
 Homologs- individual members of the
series common/trivial names
 What are alkanes primarily used for?
fuels, solvents, and lubricants
 What is the solubility of alkanes like?
They dissolve in nonpolar or weakly
polar organic solvents but don’t
dissolve in
 what is the avg density of alkanes? 0.7
g/mL
 What factor leads to an increased
boiling point/melting point in alkanes?
more carbon atoms and higher
molecular weight, because the larger
the surface area the molecule has, the
more intermolecular van der Waals
attractions must be overcome before
vaporization and boiling can occur
 why do alkanes with odd numbers of
carbons melt at lower temperatures?
Because they do not pack as well
 How does branching of the chain affect
the alkanes melting point? it increases
the melting point because it gives the
alkane a more compact 3D structure
 what are C1 and C2 used for? natural
gas
 what are C3 and C4 used for? fuels,
both for heating and combustion
engines, propellent in aerosol cans.
 what are C5 - C8 used for? constituent
of gasoline
what are C9 - C16 used for? kerosene,
jet fuel, diesal fuel, kerosene (lowest
boiling of these fuels)
 what are C16+ used for? lubricants and
heating oils
 where are most alkanes derived from?
petroleum (crude oil) and petroleum by
products
 how is petroleum refined? fractional
distillation, catalytic cracking
 catalytic cracking- converts less
valuable fractions to more valuable
products by heating alkanes in the
presence of materials that catalyze the
cleavage of large molecules into
smaller ones
 Hydrocracking- when cracking is done
in the presence of water
 methane hydrate- individual methane
molecules trapped inside cages of water
molecules
 Paraffins- another name for alkanes, as
they have a low level of reactivity due
to a lack of affinity for other reagents
 Combustion- rapid oxidation that takes
place at high temperatures, converting
alkanes to oxygen and water
 Hydrocracking- hydrogen is added to
give saturated hydrocarbons, as
cracking without hydrogen gives only
mixtures of alkanes and alkenes
 Halogenation- alkanes can react with
halogens to form alkyl halides, usually
initiated with heat or light
 Conformations- the different
arrangements formed by rotations
around a single bond
 Conformer- a specific conformation
 Newman projections- a way of drawing
a molecule looking straight down the
bond connecting two carbon atoms
 Sawhorse structures- Picture the model
looking down at an angle toward the
carbon-carbon bond
 Dihedral angle (theta)- the angle
between C-H bonds on the front and
back carbon in a newman projection.
 Eclipsed conformation- the
conformation with theta=0, hydrogens
on the back atom are hidden (eclipsed)
by those on the front carbon.
 Staggered conformation- theta = 60,
has hydrogen atoms on the back carbon
staggered half way between the front
hydrogens on the front carbon, lowest
 energy because electron clouds in the
C-H bonds are separated as much as
possible.
 Skew conformation- any other
intermediate conformation
 Torsional strain- a molecules resistance
to twisting
 torsional energy- the energy required to
twist
 Conformational analysis- the study of
energetics of different conformations
 Conformations of butane- a four carbon
alkane, C4H10. n-butane = straight
chain alkane even though it has
tetrahedral geometry. rotation around
any of the C-C bonds is possible, forms
3 special conformations: totally
eclipsed, gauche, and anti.
 Totally eclipsed conformation- when
the groups are all pointed in the same
direction and eclipse each other, higher
energy than the gauche and anti
conformations
 Gauche conformation- the molecules
are staggered (lower energy than
eclipsed)
 Anti conformation- molecules point in
opposite directions (preferred
conformation)
 Steric strain- interference (caused when
the electron clouds of two molecules
experience strong repulsion) between
two bulky groups
 Physical properties of cycloalkanes
most have acyclic properties: non polar,
relativly inert comound with boiling
and melting points that depend on their
weights.
 Ring strain- combined angle and
torsional strain. total amount energy in
cyclic compound - amount energy in
similar strain free reference compound
= extra energy due to ring strain
 Heat of combustion- the amount of heat
released when a compound is burned
with an excess of oxygen in a sealed
container (bomb calorimeter)
 Why does cyclopropane bear more ring
structure per methylene than any other
cycloalkane? there is significant angle
strain caused when the 109.5 degree
angles are compressed to 60 degrees,
which also weakens the overlap of the
C-C sp3 orbitals, which overlap at an
angle to form weaker "bent bonds".
There is significant torsional stain
because the molecule is planar and all
the bonds are eclipsed
 Why is the ring strain in cyclobutane so
high? it assumes a slightly folded form
to reduce the torsional strain that would
be caused by being a planar square, but
this adds some angle strain
 What is the conformation of
cyclopentane? Since a planar structure
would require all of the bonds to be
eclipsed, it assumes a undulating,
slightly puckered envelope
conformation that reduces eclipsing and
lowers the torsional strain.
 Why is the conformation of
cyclopentane important? the sugars
ribose and deoxyribose assume
cyclopentane like ring formations that
are crucial to the properties and
reactions of DNA
 What is the conformation of
cyclohexane? has no angle stain (all
tetrahedral angles) and no torsional
strain (no eclipsing of bonds), is not
planar.
 Why is the conformation of
cyclohexane important?Many
important compounds contain
cyclohexane like rings that are critical
to their important reactivity
 Chair conformation- the most stable
conformation in which all C-C bonds
are 109.5 degrees and in staggered
formations. allows cyclohexane to
achieve tetrahedral bond angles and
staggered conformations.
 Boat conformation- has bond angles of
109.5 and avoids angle strain, but has
torsional strain because there is
eclipsing of the bonds. Is similar to
chair conformation except the footrest
methyl group is folded upward
 Flagpole hydrogens- two of the
hydrogens on the ends of the boat that
interfere with each other due to the
eclipsing in boat conformation. stick up
like flagpoles.
 Twisted boat conformation- the slightly
skewed boat conformation a
cyclohexane will assume. the flagpole
hydrogens move away from each other
and eclipsing of the bonds is reduced.
 Half-chair conformation- the highest
energy point during the interconversion
 from the chair to boat when the footrest
of the chair flips upward. This occurs
because the energy barriers between the
2 forms are low.
 Axial bonds- one located on each C in a
cyclohexane in which the C-H bond is
directed up and down parallel to the
axis of the ring
 Equatorial bonds- one located on each
C in a cyclohexane in which the C-H
bonds are pointed out from the ring
along its equator
 What is the pattern formed by axial and
equatorial bonds on cyclohexanes? The
odd numbered C's have axial bonds up
and equatorial bonds down, the evens
are opposite
 Chair-chair interconversion or ring flip-
the twist boat, which is the intermediate
of the different orientations of axial and
equatorial
 What methylcyclohexane conformation
is lowest energy at room temp? The
chair with the methyl group in an
equatorial position
 How many gauche interactions does the
axial methylcyclohexane contain? the
equatorial? axial has 2, equatorial has
none.
 1,3-diaxial interaction- a form of a
steric strain (gauche relationship
between carbons and hydrogens places
methyl hydrogen close to the axial
hydrogens on these carbons, causing
their electron clouds to disappear)
involving carbon atoms on substituents
on carbon atoms of a ring that bear a
1,3 relationship. not found in the
equitorial formation
 How many anti relationships does the
equatorial methylcyclohexane have?
the methyl group has an anti
relationship to both C3 and C5
 Why does a larger group usually have a
larger energy difference between the
axial and equitorial positions?Because
the 1,3-diaxial interaction is stronger
for larger groups
 Is the energy difference between axial
and equatorial positions is greater for a
larger or a smaller group? Larger
 What has the most stable conformation
if both groups cannot be equitorial?
The most stable conformation has the
larger group equatorial and smaller
group axial.
 What often happens to extremely bulky
groups? They are extemely strained in
axial positions therefore most stable in
equitorial position
 What conformation is formed when
neither chair conformation will allow
the bulky groups to be equitorial? The
ring may be forced into a twisted boat
conformation
 Bicyclic or polyciclic systems- can join
two or more rings
 Fused rings- ost common, sharing 2
adjacent carbon atoms and the bond
between them.
 Bridged rings- also common, sharing 2
nonadjacent carbon atoms (the
bridgehead carbons) and one or more
carbon atoms between them (the
bridge)
 Spirocyclic compounds- rare, in which
2 rings share only 1 carbon atom
 what is the most common example of a
fused-ring system and how many
isomers does it have?
 ecaline (bicyclo[4.4.0]decane) has 2
isomers, one in which the rings are
fused using 2 cis bonds, the other fused
using 2 trans bonds.
 Why is the conformation of the cis
form flexible while the trans form is
not? Because if one of the rings in the
trans isomer did a chair-chair
conversion, the bonds to the 2nd ring
would become axial and be directed to
180 degrees apart, which is an
impossible conformation
 Chiral- object that is not
superimposable upon mirror image (no
plane of symmetry)
 Achiral- object that is superposable on
its mirror image. has a plane of
symmetry
 Stereoisomers- isomers that differ only
by the configuration of attached atoms
at one of more positions. Not
interconvertible by bond rotations
 Enantiomers- molecules that are non-
superimposable
 two requirements to be enantiomers:
(1) stereocenter (2) an atom about
which exchange of any 2 groups
produces a stereoisomer
 chiral center- tetrahedral atom bonded
to 4 different groups
 True or False: all chiral centers are
stereocenters, but not all stereocenters
are chiral centers: TRUE
 Diastereomers- stereoisomers that are
not mirror images
 two things that are true of
diastereomers:(1)absolute configuration
(2) identification of a chiral center as R
or S
 relative configuration- the relative
relationship of two chiral centers
 Enantiomers- have opposite
configuration at all chiral centers
 Diastereomers- have opposite
configuration at one or more but NOT
all stereocenters
 Epimers- diastereomers with opposite
configuration at one chiral center
 Enantiomers- have identical properties
in an achiral environment, but different
properties in a chiral environment (such
as when associated with proteins or
carbohydrates in the body)
 Diastereomers- have different
properties in all environments
 Achiral: enantiomers have identical
properties in ________ environments
 Chiral: enantiomers different properties
in a ________ environment
 Different: diastereomers have
________ properties in all
environments
 meso compound: compounds that
contain two or more chiral centers but
are achiral due to a symmetry plane
 flat polygon: when assessing the
chirality or absolute configuration of
cyclic molecules, draw the substituted
rings as _________ with wedges and
dashes.
 One: epimers are a type of diastereomer
that have opposite configuration at
______ chiral center
 what does it mean when the bonds at
chiral centers are drawn straight?
mixture of stereoisomers or the
configuration is unknown
 what does it mean when the bond at a
chiral center is wavy? exists as a
mixture of all stereoisomers
 what does it mean if the bonds at chiral
centers are drawn as rectangles that are
either solid or striped? relative
stereochemistry is known to be trans or
cis, BUT absolute configuration is
unknown.
 what does it mean if the bonds at chiral
centers are wedged or dashed? the
absolute configuration is unknown
 plane polarized light: light waves that
oscillate only in a single plane
 chiral, optically active: molecules that
rotate plane - polarized light in a
clockwise or counterclockwise
direction are ______ and _______.
 Enantiomers: can rotate plane polarized
light equally in opposite direction
 optically active: chiral diastereomers
that can have an enantiomer may also
be _________.
 Polarimeter- instrument that passes
plane-polarized light through a sample
to detect observed rotation of the light
 optically inactive, 0: with achiral
molecules, the plane-polarized light is
NOT rotated, and the sample is
_______________ so alpha =
_________.
 racemic mixture: 50:50 mixtures of two
enantiomers
 dl-, +/-, rac-: how are racemic mixtures
designated?
 Inactive: racemic mixtures are optically
_________.
 0: if optically inactive, alpha = what?
 Racemates :equal concentrations of two
enantiomers
 Dextrorotatory: with chiral, non-
racemic mixtures (not 50:50), if the
light is rotated clockwise (right) the
compound is
 d-, (+)-:how is dextrarotatory
designated?
 Levorotatory: with chiral, non-racemic
mixtures (not 50:50), if light is rotated
counterclockwise (left) the compound
is
 l-, (-)-: how are lerorotatory compounds
designated
 can optical rotation determine whether
an unknown has an R or S
configuration? NO
 specific rotation: the reported value
from after polarimetry
 What does D mean in the specific
rotation equation: degree of light of
sodium D lamp
 enantiomeric excess (optical purity,
ee): way of describing the composition
of a mixture of enantiomers. Reflects
the % excess of one enantiomer over
the other.
 chiral resolution: the process of
separating enantiomers from eachother
 Racemization: the process of
converting a single enantiomer or an
optically active mixture of enantiomers
into an optically inactive racemic
mixture
 diastereomic salts/derivatives,
enzymatic resolution, chiral
chromatography:3 methods or chiral
resolution
 it is used for the enantiomers of
naproxen in alieve. the S is good and
the R is bad for you so chiral resolution
is used to separate them, then the S is
filtered out of solution.
1. An inorganic substance which can be
transformed into urea.
2. A description of detailed pathways by
which compound is converted into another.
3. Is a derivative of saturated hydrocarbon
in which hydrogen atom is replaced by a
halogen.
4. An acid that is shaken at room
temperature to convert the very reactive
tertiary butyl alcohol to the chloride.
5. Lucas Reagent
6. This is not suitable for the laboratory
preparation of alkyl halides because of low
percent yield and is difficult to separate it
from its isomers.
7. Characteristics of alkyl halides:
A. RX have higher boiling point than
alkanes with the same number of carbon
atoms.
B. For a given Alkyl group, boiling point
increases with increasing atomic weight of
halogen.
C. For a given halogen, boiling point
increases with increasing number of carbon
atoms.
D. Alkyl Halides are insoluble with water
but they are soluble in organic solvents like
ether, benzene, CHCl3, and ligroin.
E. Iodo, bromo and polychloro compounds
are much denser than water.
8. The electrons of the bonding pair are
taken away or provided singly; carried out
in gas phase or solvents.
9. The electrons of the bonding pair are
taken away or provided in pairs; carried out
in solution.
10. This are the basic electron-rich reagents
that tends to attack the nucleus of the
carbon.
11. Displacement by anion
12. What is the product of the
dehydrogenation of Alky Halides?
13. An amorphous powder which
hydrolyses rapidly and inflames
spontaneously in air.
14. Reaction of alkyl halide with sodium
15. Is the study of hydrocarbons and their
derivatives.
16. The father of Organic Chemistry
17. The same molecular formula but
different structural formula and differs in
their physical and chemical properties.
18. The alcohol that can be accepted by the
body
19. Contains all genetic information
20. Catalyze all reactions in the body
21. Is the prime requisite for understanding
chemistry
22. Is the three dimensional arrangement of
atoms in a molecule.
23. Accounts for the geometric arrangement
of electron pairs around a central atom in
terms of electrostatic repulsion.
24. Are saturated aliphatic hydrocarbons
characterized by single covalent bonds
between carbon atoms.
25. Alkanes are also called as
26. Are alkanes with one of the hydrogen
atom removed from the C-H bond, they are
usually the substituents or branches.
27. Are unsaturated aliphatic hydrocarbons
characterized by the presence of a double
covalent bond.
28. Alkenes are also known as
29. Substituents on the same side are
30. Substituents on the opposite side are
31. Compounds with two double covalent
bonds are called
32. Compounds with three double covalent
bonds are called
33. Are unsaturated aliphatic hydrocarbons
characterized by a triple covalent bond in
the parent chain.
34. Known for their fragrance and aroma.
35. Aromatic compounds are called
36. Are halogen derivatives of hydrocarbon
37. Are halogen derivatives of aromatic
hydrocarbons.
38. Are hydroxy derivatives derivatives of
hydrocarbons
39. Are alkoxy derivatives derivatives of
hydrocarbons
40. Are carbonyl derivatives derivatives of
hydrocarbons
41. A test that distinguishes aldehydes from
ketones or the silver mirror test for
aldehydes.
42. Are carbonyl derivatives of
hydrocarbons where two other C atoms are
attached to the carbonyl c
43. Test for the presence of sugar
44. From oil of jasmine
45. Are caboxyl derivatives of hydrocarbons
46. An acid in rancid butter
47. An acid in buttr fat of milk
48. Are straight chain aliphatic acids
49. Are products of an esterification process
when an organic acid is heated with a
primary or secondary alcohol in the
presence of metal catalyst.
50. Are cyclic esters
51. Are pleasant smelling substances
responsible for the flavors and fragrances or
fruits and flowers.
52. Artificial rum flavors
53. Present in oranges
54. Present in apricot
55. A common solvent for glues, nail polish,
paints and lacquers
56. A lactone, pleasant odor of a newly
mown hay.
57. Present in bananas
58. Present in pineapples
59. Prepared from acids by reaction with
thionyl chloride, SOCl2, or phosphorous
halides, PX5.
60. Produced when two acids are
dehydrated.
61. An acid that cannot form a cyclic
anhydride
62. An acid with a cis-carbonyl group
readily forms a cyclic anhydride when
heated
63. Occurs in the cell sap of any plants
usually as a salt.
64. Is the most common salicylate.
65. Esters that are used as antipyretics.
66. Chief component of oil of wintergreen,
used in rubbing liniments where its mild
irritating action on the skin provides a
counter-irritant for sore muscles.
67. Plays an important role in the
metabolism of carbohydrates
68. Are products of an esterification process
when an organic acid is heated with a
primary or secondary alcohol in the
presence of metal catalyst.
69. An alkyl or aryl derivatives of ammnia
70. Most commercially important amine
71. Are acyl derivatives of ammonia.
72. Is used as antipyretic
73. Is a special amide, end product of
metabolism of proteins, and excreted in
urine
74. The simplest of the diamides, prepared
by reacting ammonia with ethylene
dichloride.
75. Product of the reaction of ethylene
diamide with chloroacetic acid.
76. Foul smelling, formed when animal
flesh decays.
77. Same as putrescine
78. Most important commercial diamide as
raw material in nylon manufacture.
79. Formed when adipic acid and
hexamethylenediamide is treated together
80. Are sulfur analogs of alcohols
81. Is the component of the yellow liquid
that shunks when threatened
82. Are products of sulfonation of an alkyl
or aromatic group.
83. Not mirror images
84. Mirror images but not superimposable
85. Used as anti-knocking agent in gasoline
86. These substances are used to salt out
proteins
87. It is used in the treatment of burns,
because it produces an astringent effect on
the tissues and prevents absorption.
88. Used to relieve diarrhea and to check
secretions in the treatment of burns.
89. Used to precipitate and remove proteins
in blood analysis.
90. Are building blocks of proteins.
91. A jelly-like colloidal substance
conceived as the physical basis of all life.
92. An amide bond that links one amino
acid to another.
93. They are the constituents present in all
living things.
94. This is a specific test for proteins and
substances which contain the peptide
linkage; test for unhydrolyzed proteins.
95. Biuret Test: Protein + NaOH + CuSO4
→ _____ color
96. This is a test for the presence of benzene
ring or aromatic nucleus; eg. Tyrosine,
tryptophan, phenylanine
97. Xanthoproteic Test: Protein + Conc.
HNO3 → _____ color
98. This is a test for the presence of a
phenolic group in proteins.
99. An amino acid that contains a phenolic
group will give a positive result in Millon’s
test.
100. Mercuric + Mercurous Nitrate in
HNO3 is a ________.
101. Protein (containing phenolic group) +
Millon’s Reagent =
102. This a test for the indole nucleus in
proteins.
103. This is a general test for alpha amino
acids.
104. Protein in eggs.
105. Protein in blood.
106. An inorganic substance that is used as
an explosive and circulatory depressant.
107. It is used to lower blod pressure.
108. It is any metallic salt of higher fatty
acids.
109. Alkaline hydrolis of fats and oils to
produce soap.
110. Contains mercuric iodide to destroy
microorganisms.
111. Are simpler proteins linked with non
protein groups.
112. Are proteins linked with a colored
compound.
113. Proteins linked with carbohydrates.
114. Protein in milk.
115. Insoluble protein product produced by
the action of heat/alcohol.
116. An ether used as refrigerant especially
in the quick freezing of foods.
117. A property of sugar solution to change
the rotary power of a freshly prepared sugar
solution.
118. A chemical reaction wherein sugar are
converted into alpha with the aid of enzyme.
119. A raw material that can be used to
produce whisky.
120. A sugar acid when the -CHO group is
oxidized.
121. A sugar acid formed when the -
CH2OH group is oxidized.
122. A sugar acid formed when both the
aldehyde and second degree alcohol is
oxidized.
123. When fructose undergoes partial
oxidation it will yield ______________.
124. Partial oxidation of galactose, will
yield ______________.
125. A specific test for galactose
126. A yellow crystalline solid formed when
sugar reacts with hydrazine.
127. The breaking down of sugar in much
simpler forms.
128. Are a heterogeneous class of naturally
occurring organic substances, this means
“fat” or “lard”.
129. Building blocks of lipids
130. An animal sterol.
131. A plant sterol.
132. anomeric carbon: carbon atom that was
the carbonyl carbon atom in the straight-
chain form of a monosaccharide
133. Mutarotation: the ongoing
interconversion between anomeric forms of
a monosaccharide to form an equilibrium
mixture
134. reducing sugar: any carbohydrate
capable of reducing a mild oxidizing agent
(such as Tollens' or Benedict's reagents)
without first undergoing hydrolysis
135. glycosidic linkage: carbon-oxygen-
carbon linkage between monosaccharide
units in more complex carbohydrates, such
as disaccharides or polysaccharides.
136. lactose intolerant: inability to digest the
lactose found in milk or dairy products due
to a deficiency of the enzyme lactase
137. Galactosemia: genetic disease caused
by the absence of one of the enzymes
needed to convert galactose to glucose
138. Tollen's reagent: reagents used to
detect the presence of reducing sugars
- utilizes Ag(NH3)2 + as an oxidizing agent
- in positive Tollen's test, aldehydes reduce
Ag+ to metallic silver
139. Benedict's reagent: reagents used to
detect the presence of reducing sugars
- aldehyde group of an aldose is readily
oxidized
- indicated by a red precipitate of Cu2O
140. Iodine: well-known reagent that tests
for the presence of starch
- fits inside the helix conformation amylose
typically makes.