Organic Chemistry Test Flashcards
1
Q
Alkanes
A
bond: single
suffix: –ane
prefix: indicates the longest straight chain in the mlecule
2
Q
Alkyl Branches
A
named with the prefix for the branch, followed by the suffix –yl
3
Q
Naming Hydrocarbons
A
numerals are separated by commas
numerals and letters by hyphens
names of branches and parent chains are NOT separated
4
Q
Steps of Naming an Alkane
A
- identify the LONGEST carbon chain (it may travel through branches)
- number the carbon atoms, starting with the end closest to the branch(es)
- name each branch and identify its location –branch name parent name
- write IUPAC name: number of location – branch nameparent name
- list branches in alphabetical order
5
Q
Cyclic Hydrocarbons Prefix
A
cyclo–
6
Q
Alkenes
A
bond: double
suffix: –ene
prefix: indicates the longest straight chain in the mlecule
7
Q
Alkynes
A
bond: triple
suffix: –yne
prefix: indicates the longest straight chain in the mlecule
8
Q
Steps of Naming an Alkene/Alkyne
A
SAME STEPS AS NAMING ALKANE
but when numbering carbon atoms in the parent chain, begin with the end closest to the multiple bond.
Insert hyphens between the branch chain and the parent chain to denote where the carbon double or triple bond is located
e.g. 3-methyl-1-butene OR 3-methylbut-1-ene
9
Q
When there are multiple alkyl branches on an alkane…
A
there is a prefix in front of the side chain name
di– tri– tetra–…
10
Q
When there are multiple double or triple bonds on an alkene/alkyne…
A
their locations are indicated by the prefixes di– tri– tetra–…
11
Q
Aromatic Hydrocarbons
A
In simple aromatics, the benzene ring is the parent with alkyl groups named as branches
(YOU DO NOT HAVE TO NUMBER THE BRANCH IF THERE IS ONLY 1 PRESENT)
12
Q
If the aromatic ring is considered the side chain…
A
the prefix phenyl– is used
13
Q
Nomenclature of Hydrocarbons
A
No. of C Atoms Prefix Side Chain Prefix for Substituents
1 meth- meth-
2 eth- eth- di-
3 prop- prop- tri-
4 but- but- tetra-
5 pent- pent- penta-
6 hex- hex- hexa-
7 hept- hept- hepta-
8 oct- oct- octa
9 non- non-
10 dec dec
14
Q
Nomenclature of Alkenes and Alkynes
A
when you reach 4 carbons, you must specify the location of the double or triple bond
15
Q
Propyl Side Chain
A
can attach 2 different ways:
1. can attach in a line formation with an ending carbon
n-propyl
- with its middle carbon attached to the parent
isopropyl
16
Q
Butyl
A
can attach four different ways:
1. with an ending carbon
n-butyl
- with the second carbon in the chain
sec-butyl / s-butyl - in an upper case “T”
isobutyl - in a lower case “t”
tert-butyl / t-butyl
17
Q
Cyclic Hydrocarbons
A
are aliphatic hydrocarbon chains that form rings
–need at least 3 carbons to form a cyclic hydrocarbon
prefix: cyclo-
18
Q
Aliphatic
A
means they do not contain benzene
19
Q
Note about cyclic hydrocarbons
A
the cyclic hydrocarbon is considered a side group (cyclo__yl-) instead of the root if it is attached to a hydrocarbon chain with a greater number of carbons
20
Q
Properties of Cyclic Hydrocarbons
A
- non-polar; are insoluble in water
- physical properties are similar to straight-chain counterparts with the same number of carbon atoms
- melting and boiling points are higher than straight-chain counterparts due to stronger intermolecular attractions (London Dispersion Forces)
21
Q
Aromatic Hydrocarbons
A
are derived from a benzene ring
-hydrocarbon ring with 3 double bonds, 1 hydrogen atom bound to each carbon atom (C6H6)
22
Q
Note
A
benzene is considered a side group (phenyl–) instead of the root if it is attached to a hydrocarbon chain with more than 6 carbons
23
Q
Note
A
if there is only 1 substituent on the benzene ring, you do not specify the location
24
Q
Properties of Aromatic Hydrocarbons
A
- non-polar; insoluble in water
- benzene is a liquid at standard temperature
- boiling points are similar to aliphatic hydrocarbons with the same number of carbon atoms because they have similar molar masses
- strong odours
25
Isomers
molecules with the same molecular formula, but with atoms in different arrangements
2 main classes: constitutional isomers and stereoisomers
26
Constitutional Isomers
molecules with the same molecular formula with atoms bonded together in a different sequence
AKA structural isomers
27
Properties of Constitutional Isomers
- those with more branches have lower boiling points due to a decrease in surface area and a decrease in attractive forces (London Dispersion Forces)
28
Stereoisomers
molecules with the same molecular formula and atoms bonded in the same sequence, but they differ in 3D orientations of atoms in space
2 types: diastereoisomers and enantiomers
29
Diastereoisomers
based on a double bond in which different types of atoms or group are bonded to each carbon in the double bond
AKA geometric isomers
30
Cis Isomer
when the larger atoms or groups are on the same side of the double bond
31
Trans Isomer
when the larger atoms or groups are on opposite sides of the double bond
32
Enantiomers
molecules that are mirror images of each other around a single carbon atom bonded to 4 different types of atoms or groups
- they cannot be superimposed on top of each other
33
Alcohols
hydrocarbon derivatives that contain a hydroxyl (–OH) functional group
34
1˚ Alcohols
the carbon atom bearing the –OH group is attached to ONE other alkyl group
35
2˚ Alcohols
the carbon atom bearing the –OH group is attached to TWO alkyl groups
36
3˚ Alcohols
the carbon atom bearing the –OH group is attached to THREE alkyl groups
37
Naming Alcohols
1. Identify the root: how many carbons are in the longest chain
DROP THE "e" if a single –OH group is present
2. Identify the suffix: –ol
* ensure the alcohol has the lowest number when it is the parent chain*
3. Identify the side chain(s)
4. Name the compound
38
Physical Properties of Alcohols
- hydroxyl group (–OH) is very polar which makes small alcohols polar and soluble in water
- polarity and solubility decrease as the length of the hydrocarbon chain increases
- boiling points of alcohols are much higher than alkanes with the same number of carbon atoms due to HYDROGEN BONDING and DIPOLE INTERACTIONS
- they are toxic
39
Ethers
hydrocarbon derivatives in which an oxygen atom is single bonded to 2 carbon atoms (–O– functional group)
40
Naming Ethers
alkoxy group: the –R group with LESS carbon atoms
- named in the prefix
- add "-oxy" after the name (ex. ethoxy)
parent chain: the –R group with MORE carbon atoms
- is named in the suffix (ex. butane)
- the first number in the name tells you which carbon of the parent is attached to the oxygen
side groups are named AFTER the alkoxy prefix
------------------------------------------------------------------------------------------------------------
alkoxy - side chains - parent chain
ex: 2-ethoxybutane, 1-methoxy-4-methylpentane
41
When numbering the carbons in an ether...
start numbering from the end closest to the oxygen
42
Physical Properties of Ethers
- bond angle makes ethers slightly polar (DIPOLE INTERACTIONS)
2-3 carbons: soluble in water
4-6 carbons: slightly soluble in water
7+: insoluble in water
longer carbon chain = less polar
- ethers with a total of 2-3 carbons are gases at room temp while larger ether are liquids at room temp
43
Alcohol contains which functional group?
hydroxyl –OH
44
Hydroxyl –OH is in what?
Alcohol
45
What is the smaller carbon chain attached to an ether is called?
alkoxy group
46
An alkoxy group is in what?
Ethers
47
Aldehydes
contain the carbonyl (C=O) functional group
| - carbon double bonded to oxygen
48
Where are aldehydes located?
aldehydes are ALWAYS found at the END of a hydrocarbon chain
49
*Note*
in aldehydes, the carbonyl group is part of the formyl functional group (–CHO)
50
Naming Aldehydes
1. Identify the root: how many carbons are in the longest chain?
DROP THE "E: AT THE END OF THE PARENT ALKANE
2. Identify the suffux: –al
3. Identify the side chains
4. Name the compound
51
*Note*
aldehydes: Carbon 1 is the carbon attached to the carbonyl
52
Physical Properties of Aldehydes
- carbonyl group is polar, but the carbon-hydrogen bonds are non-polar
-boiling points are lower than alcohols with the same number of carbon atoms due to a lack of intermolecular hydrogen bonding
- at room temp: the longer the carbon chain = more solid
1-4 carbons: soluble in water
5-7 carbons: slightly soluble in water
8+ carbons: insoluble in water
- short-chain aldehydes have strong, pungent odours; longer ones have more pleasant smells
53
Aldehydes contain which functional group?
carbonyl (C=O)
54
A Carbonyl that is only bonded to 1 carbon/chain is in what?
Aldehydes
55
Keytones
contain the carbonyl (C=O) functional group
| –––> unlike aldehydes, the carbon atom in the carbonyl is bonded to 2 carbon atoms or chains
56
Where are Keytones located?
anywhere on the hydrocarbon chain EXCEPT on the END
57
How many carbons does the smallest Keytone contain?
3 carbon atoms (propanone)
58
Naming Keytones
1. Identify the root: how many carbons are in the longest chain?
DROP THE "e" AT THE END OF THE PARENT ALKANE
2. Identify the suffix: –one
* start numbering at the end closest to the keytone*
3. Identify side chains
4. Name the compound
59
*Note*
only number the keytone if there are 5+ carbons in the parent chain
60
Physical Properties of Ketones
- the carbonyl group is polar, but the carbon-hydrogen bonds are non-polar
- slightly less polar than aldehydes
- boiling points are lower than alcohols with the same number of carbon atoms due to lack of intermolecular hydrogen bonding
- at room temp: the longer the carbon chain = more solid
61
Keytones contain which functional group?
carbonyl (C=O)
62
A Carbonyl that is bonded to 2 carbons/chains is in what?
Keytones
63
Organic Halides
hydrocarbons that contain at least 1 halogen atom (group 17 of the periodic table)
64
Haloalkane
an organic halide consisting of only single bonds
65
Naming Organic Halides
1. Identify the root: how many carbons are in the longest chain?
```
2. Identify the side chains/prefixes:
Cl = chloro-
F = fluoro
Br = bromo-
I = iodo-
```
3. Name the compound
66
Physical Properties of Organic Halides
- the smallest haloalkanes consisting of 1 carbon atom are slightly soluble in water, all others are insoluble in water because hydrocarbon chains are non-polar
- boiling points of haloalkanes are higher than alkanes with the same number of carbon atoms due to an increase in LONDON DISPERSION FORCES and DIPOLE INTERACTIONS
67
Carboxylic Acid
an aldehyde that has been oxidized, which has 3 bonds to oxygen (2 in a CARBONYL and 1 in an HYDROXYL)
–––> together they form a carboxyl group
68
Naming Carboxylic Acids
- they are named ALKANOIC ACID
- often a number is not needed for simple carboxylic acids because the functional group is AT THE END OF THE CHAIN
- if a carboxylic acid is located at both ends of a chain, the suffix –dioc is used
69
Where are is a carboxyl located?
at the end of the hydrocarbon chain
70
Example of a carboxylic acid:
propanedioic acid
71
Physical Properties of Carboxylic Acids
- due to the presence of the carboxyl group, carboxylic acids are even more polar and water soluble than alcohols and have higher melting points
- participate in hydrogen bonding, dipole interactions, and london dispersion forces
- they form organic salts in neutralization reactions by mixing with a base
72
Creating a carboxylic acid
alcohol –––> aldehyde –––> carboxylic acid
e.g. ethanol –––> ethanal –––> ethanoic acid
73
Carboxylic Acids contain which functional group?
carboxyl
74
A Carboxyl is in what?
carboxylic acids
75
What 2 functional groups combine together to form an ester, and water as products?
Alcohols and carboxylic acids
76
Alcohols and carboxylic acids combine together to form what?
an ester and water
77
What type of reaction is an esterification reaction?
a condenstation, substitution reaction
78
The condensation, substitution reaction of an alcohol and carboxylic acid is called what?
esterification
79
General formula for an ester
RCOOR
80
Where does the first half of the RCOOR ester formula come from?
RCO- carboxylic acid
81
Where does the second half of the RCOOR ester formula come from?
-OR alcohol
82
What happens during esterification?
the hydroxyl group from the carboxylic acid gets removed and the hydroxyl group from the alcohol loses its hydrogen to form WATER
83
Naming Esters
Esters are names alkyl alkanoate
- the chain with the carbonyl group is placed second, even if it is shorter
the ending of the participating acid is changed from –oic acid to –oate
84
How do you name an ester if there are side chains?
start numbering from the carbon attached to the hydroxyl
85
An Ester is named like:
alkyl from the alcohol (space) then ___-oate from the carboxylic acid
ALCOHOL THEN CARBOXYLIC ACID
86
What 2 functional groups make up an ester?
alcohols and carboxylic acids
87
Physical Properties of Esters
- have the polar carbonyl but no alcohol group, so they are between alkanes and alcohols in physical properties
- not acidic
- fragrant and are found in placne
- can be joined together to form long chains called, "polyesters"
88
How can esters be broken down?
via Hydrolysis Reactions: adding water to the ester along with a sulfuric acid catalyst with return the carboxylic acid and alcohol the ester was made from
89
What is formed when an ester is heated with excess water and a strong base?
it will break the ester into the carboxylic acid salt and alcohol
90
What happens during a saponification reaction?
the long chain acids of fats and oils are used to form soap
91
Primary Amine 1˚
1 alkyl chain is attached to the nitrogen
92
Secondary Amine 2˚
2 alkyl chains are attached to the nitrogen
93
Tertiary Amine 3˚
3 alkyl chains are attached to the nitrogen
94
Naming Amines: Primary
amines are named as aminoalkanes
| –––> AMINO ALWAYS COMES BEFORE THE PARENT GROUP
95
Naming Amines: Secondary
N-alkylaminoalkane
96
Naming Amines: Tertiary
N-alkyl-N-alkylaminoalkane
97
Physical Properties of Amines
- polar (hydrogen bonding (N-H) and dipole attractions (N-C)) but not quite as polar as alcohols
- unpleasant odours
98
What do amines react with to form organic salts?
| What type of reaction is this?
they are organic bases that can react with CARBOXYLIC ACIDS to form ORGANIC SALTS (amides)
condensation reaction
99
How are amines prepared?
by reacting ammonia with halogenated hydrocarbons
the halogen of the alkylhalide reacts with a hydrogen from the ammonia and combines to form a hydrogen halide + an amine
100
Naming Amides: Primary
alkaneamide
101
Naming Amide: Secondary/Tertiary
N-alkyl alkanamide
102
How are amides named for SECONDARY/TERTIARY?
first part of the name is derived from the amine
| second part is from the carboxylic acid
103
How are amides prepared?
carboxylic acids react with ammonia, primary and secondary amines to produce amides
104
What type of reaction occurs when amides are prepared?
condensation, substitution reaction
105
Properties of Amides
- have the polar carbonyl group and may have a polar N-H bond, but they are less polar than amines and alcohols because they don't always have hydrogen bonding
- weak bases
-generally insoluble in water
can be hydrolyzed like esters but are slower to react under the same conditions
–––> a carboxylic and amine would result
106
Polymers
long chains of molecules made up of many repeating units (monomers)
107
Polymerization
process of polymers forming
108
Condensed Form of Polymers
[-open monomer-]n
109
What are the 2 types of polymerization reactions?
1. Addition Polymerization
| 2. Condensation
110
Addition Polymers
polymers formed through addition polymerization
| –––> they form by chain addition reactions between monomers that have a DOUBLE BOND
111
What are the 3 steps to form an addition polymer
1. Initiation
2. Propagation
3. Termination
112
When drawing a polymer...
make sure to draw on the vertical axis to allow other molecules to attach at the sides
113
Condensation Polymers
polymers formed through condensation polymerization
| –––> they are di-functional meaning they have 2 FUNCTIONAL GROUPS
114
What are the 2 types of condensation polymers?
polyester and polyamide
115
Polyester
2 different monomers are involved and are held together by ester linkages
116
What are the 2 different monomers involved in the condensation of polyester?
1. Dicarboxylic Acid Monomer
(contains 2 carboxylic acids groups)
2. Diol Monomer
(contains 2 alcohol groups)
117
How do the 2 monomers of a polyester condensation reaction combine?
the dicarboxylic acid gives up its -OH group and the diol monomer gives up a hydrogen atom from its -OH group, creating a water molecule
now the carbon atom on the dicarboxylic acid is able to directly bond to the oxygen atom on the diol, forming an ESTER LINKAGE
118
How do you make/show a polyester as a repeating unit?
remove the -OH and H from the ends to make another water molecule, which in turn allows for more monomers to be added on to lengthen the chains
119
What are the 2 different monomers involved in the condensation of polyamide?
1. Dicarboxylic Acid Monomer
(contains 2 carboxylic acids groups)
2. Diamine Monomer
(contains 2 amino groups)
120
How do the 2 monomers of a polyamide condensation reaction combine?
the dicarboxylic acid gives up its -OH group and the diamine monomor gives up a hydrogen atom from its amino group, creating a water molecule
now the carbon atom on the dicarboxylic acid is able to bond directly to the nitrogen atom on the diamine monomer, forming an AMIDE LINKAGE
121
How do you make/show a polyamide as a repeating unit?
remove the -OH and H from the ends to make another water molecule, which in turn allows for more monomers to be added on to lengthen the chain
122
ethoxy corresponds to what functional group?
ethers
123
Which functional group has oate as a suffix?`
esters
124
Which 2 functional groups are the only ones with a space in their name?
esters and amide
125
Naming secondary/tertiary amides:
amine then carboxylic acid
126
Naming primary amides:
carboxylic acid then amine
