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Organic Chemistry Test Flashcards

1
Q

Alkanes

A

bond: single
suffix: –ane
prefix: indicates the longest straight chain in the mlecule

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2
Q

Alkyl Branches

A

named with the prefix for the branch, followed by the suffix –yl

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3
Q

Naming Hydrocarbons

A

numerals are separated by commas
numerals and letters by hyphens
names of branches and parent chains are NOT separated

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4
Q

Steps of Naming an Alkane

A
  1. identify the LONGEST carbon chain (it may travel through branches)
  2. number the carbon atoms, starting with the end closest to the branch(es)
  3. name each branch and identify its location –branch name parent name
  4. write IUPAC name: number of location – branch nameparent name
  5. list branches in alphabetical order
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5
Q

Cyclic Hydrocarbons Prefix

A

cyclo–

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6
Q

Alkenes

A

bond: double
suffix: –ene
prefix: indicates the longest straight chain in the mlecule

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7
Q

Alkynes

A

bond: triple
suffix: –yne
prefix: indicates the longest straight chain in the mlecule

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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

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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–…

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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–…

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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)

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12
Q

If the aromatic ring is considered the side chain…

A

the prefix phenyl– is used

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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

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14
Q

Nomenclature of Alkenes and Alkynes

A

when you reach 4 carbons, you must specify the location of the double or triple bond

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15
Q

Propyl Side Chain

A

can attach 2 different ways:
1. can attach in a line formation with an ending carbon
n-propyl

  1. with its middle carbon attached to the parent
    isopropyl
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16
Q

Butyl

A

can attach four different ways:
1. with an ending carbon
n-butyl

  1. with the second carbon in the chain
    sec-butyl / s-butyl
  2. in an upper case “T”
    isobutyl
  3. in a lower case “t”
    tert-butyl / t-butyl
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17
Q

Cyclic Hydrocarbons

A

are aliphatic hydrocarbon chains that form rings
–need at least 3 carbons to form a cyclic hydrocarbon
prefix: cyclo-

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18
Q

Aliphatic

A

means they do not contain benzene

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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

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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)
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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)

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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

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23
Q

Note

A

if there is only 1 substituent on the benzene ring, you do not specify the location

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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
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25
Q

Isomers

A

molecules with the same molecular formula, but with atoms in different arrangements

2 main classes: constitutional isomers and stereoisomers

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26
Q

Constitutional Isomers

A

molecules with the same molecular formula with atoms bonded together in a different sequence
AKA structural isomers

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27
Q

Properties of Constitutional Isomers

A
  • those with more branches have lower boiling points due to a decrease in surface area and a decrease in attractive forces (London Dispersion Forces)
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28
Q

Stereoisomers

A

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

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29
Q

Diastereoisomers

A

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

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30
Q

Cis Isomer

A

when the larger atoms or groups are on the same side of the double bond

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31
Q

Trans Isomer

A

when the larger atoms or groups are on opposite sides of the double bond

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32
Q

Enantiomers

A

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
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33
Q

Alcohols

A

hydrocarbon derivatives that contain a hydroxyl (–OH) functional group

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34
Q

1˚ Alcohols

A

the carbon atom bearing the –OH group is attached to ONE other alkyl group

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35
Q

2˚ Alcohols

A

the carbon atom bearing the –OH group is attached to TWO alkyl groups

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36
Q

3˚ Alcohols

A

the carbon atom bearing the –OH group is attached to THREE alkyl groups

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37
Q

Naming Alcohols

A
  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
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38
Q

Physical Properties of Alcohols

A
  • 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
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39
Q

Ethers

A

hydrocarbon derivatives in which an oxygen atom is single bonded to 2 carbon atoms (–O– functional group)

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40
Q

Naming Ethers

A

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

alkoxy - side chains - parent chain
ex: 2-ethoxybutane, 1-methoxy-4-methylpentane

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41
Q

When numbering the carbons in an ether…

A

start numbering from the end closest to the oxygen

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42
Q

Physical Properties of Ethers

A
  • 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
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43
Q

Alcohol contains which functional group?

A

hydroxyl –OH

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44
Q

Hydroxyl –OH is in what?

A

Alcohol

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45
Q

What is the smaller carbon chain attached to an ether is called?

A

alkoxy group

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46
Q

An alkoxy group is in what?

A

Ethers

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47
Q

Aldehydes

A

contain the carbonyl (C=O) functional group

- carbon double bonded to oxygen

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48
Q

Where are aldehydes located?

A

aldehydes are ALWAYS found at the END of a hydrocarbon chain

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49
Q

Note

A

in aldehydes, the carbonyl group is part of the formyl functional group (–CHO)

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50
Q

Naming Aldehydes

A
  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
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51
Q

Note

A

aldehydes: Carbon 1 is the carbon attached to the carbonyl

52
Q

Physical Properties of Aldehydes

A
  • 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
Q

Aldehydes contain which functional group?

A

carbonyl (C=O)

54
Q

A Carbonyl that is only bonded to 1 carbon/chain is in what?

55
Q

Keytones

A

contain the carbonyl (C=O) functional group

–––> unlike aldehydes, the carbon atom in the carbonyl is bonded to 2 carbon atoms or chains

56
Q

Where are Keytones located?

A

anywhere on the hydrocarbon chain EXCEPT on the END

57
Q

How many carbons does the smallest Keytone contain?

A

3 carbon atoms (propanone)

58
Q

Naming Keytones

A
  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
Q

Note

A

only number the keytone if there are 5+ carbons in the parent chain

60
Q

Physical Properties of Ketones

A
  • 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
Q

Keytones contain which functional group?

A

carbonyl (C=O)

62
Q

A Carbonyl that is bonded to 2 carbons/chains is in what?

63
Q

Organic Halides

A

hydrocarbons that contain at least 1 halogen atom (group 17 of the periodic table)

64
Q

Haloalkane

A

an organic halide consisting of only single bonds

65
Q

Naming Organic Halides

A
  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-
  1. Name the compound
66
Q

Physical Properties of Organic Halides

A
  • 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
Q

Carboxylic Acid

A

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
Q

Naming Carboxylic Acids

A
  • 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
Q

Where are is a carboxyl located?

A

at the end of the hydrocarbon chain

70
Q

Example of a carboxylic acid:

A

propanedioic acid

71
Q

Physical Properties of Carboxylic Acids

A
  • 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
Q

Creating a carboxylic acid

A

alcohol –––> aldehyde –––> carboxylic acid

e.g. ethanol –––> ethanal –––> ethanoic acid

73
Q

Carboxylic Acids contain which functional group?

74
Q

A Carboxyl is in what?

A

carboxylic acids

75
Q

What 2 functional groups combine together to form an ester, and water as products?

A

Alcohols and carboxylic acids

76
Q

Alcohols and carboxylic acids combine together to form what?

A

an ester and water

77
Q

What type of reaction is an esterification reaction?

A

a condenstation, substitution reaction

78
Q

The condensation, substitution reaction of an alcohol and carboxylic acid is called what?

A

esterification

79
Q

General formula for an ester

80
Q

Where does the first half of the RCOOR ester formula come from?

A

RCO- carboxylic acid

81
Q

Where does the second half of the RCOOR ester formula come from?

A

-OR alcohol

82
Q

What happens during esterification?

A

the hydroxyl group from the carboxylic acid gets removed and the hydroxyl group from the alcohol loses its hydrogen to form WATER

83
Q

Naming Esters

A

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
Q

How do you name an ester if there are side chains?

A

start numbering from the carbon attached to the hydroxyl

85
Q

An Ester is named like:

A

alkyl from the alcohol (space) then ___-oate from the carboxylic acid

ALCOHOL THEN CARBOXYLIC ACID

86
Q

What 2 functional groups make up an ester?

A

alcohols and carboxylic acids

87
Q

Physical Properties of Esters

A
  • 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
Q

How can esters be broken down?

A

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
Q

What is formed when an ester is heated with excess water and a strong base?

A

it will break the ester into the carboxylic acid salt and alcohol

90
Q

What happens during a saponification reaction?

A

the long chain acids of fats and oils are used to form soap

91
Q

Primary Amine 1˚

A

1 alkyl chain is attached to the nitrogen

92
Q

Secondary Amine 2˚

A

2 alkyl chains are attached to the nitrogen

93
Q

Tertiary Amine 3˚

A

3 alkyl chains are attached to the nitrogen

94
Q

Naming Amines: Primary

A

amines are named as aminoalkanes

–––> AMINO ALWAYS COMES BEFORE THE PARENT GROUP

95
Q

Naming Amines: Secondary

A

N-alkylaminoalkane

96
Q

Naming Amines: Tertiary

A

N-alkyl-N-alkylaminoalkane

97
Q

Physical Properties of Amines

A
  • polar (hydrogen bonding (N-H) and dipole attractions (N-C)) but not quite as polar as alcohols
  • unpleasant odours
98
Q

What do amines react with to form organic salts?

What type of reaction is this?

A

they are organic bases that can react with CARBOXYLIC ACIDS to form ORGANIC SALTS (amides)

condensation reaction

99
Q

How are amines prepared?

A

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
Q

Naming Amides: Primary

A

alkaneamide

101
Q

Naming Amide: Secondary/Tertiary

A

N-alkyl alkanamide

102
Q

How are amides named for SECONDARY/TERTIARY?

A

first part of the name is derived from the amine

second part is from the carboxylic acid

103
Q

How are amides prepared?

A

carboxylic acids react with ammonia, primary and secondary amines to produce amides

104
Q

What type of reaction occurs when amides are prepared?

A

condensation, substitution reaction

105
Q

Properties of Amides

A
  • 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
Q

Polymers

A

long chains of molecules made up of many repeating units (monomers)

107
Q

Polymerization

A

process of polymers forming

108
Q

Condensed Form of Polymers

A

[-open monomer-]n

109
Q

What are the 2 types of polymerization reactions?

A
  1. Addition Polymerization

2. Condensation

110
Q

Addition Polymers

A

polymers formed through addition polymerization

–––> they form by chain addition reactions between monomers that have a DOUBLE BOND

111
Q

What are the 3 steps to form an addition polymer

A
  1. Initiation
  2. Propagation
  3. Termination
112
Q

When drawing a polymer…

A

make sure to draw on the vertical axis to allow other molecules to attach at the sides

113
Q

Condensation Polymers

A

polymers formed through condensation polymerization

–––> they are di-functional meaning they have 2 FUNCTIONAL GROUPS

114
Q

What are the 2 types of condensation polymers?

A

polyester and polyamide

115
Q

Polyester

A

2 different monomers are involved and are held together by ester linkages

116
Q

What are the 2 different monomers involved in the condensation of polyester?

A
  1. Dicarboxylic Acid Monomer
    (contains 2 carboxylic acids groups)
  2. Diol Monomer
    (contains 2 alcohol groups)
117
Q

How do the 2 monomers of a polyester condensation reaction combine?

A

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
Q

How do you make/show a polyester as a repeating unit?

A

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
Q

What are the 2 different monomers involved in the condensation of polyamide?

A
  1. Dicarboxylic Acid Monomer
    (contains 2 carboxylic acids groups)
  2. Diamine Monomer
    (contains 2 amino groups)
120
Q

How do the 2 monomers of a polyamide condensation reaction combine?

A

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
Q

How do you make/show a polyamide as a repeating unit?

A

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
Q

ethoxy corresponds to what functional group?

123
Q

Which functional group has oate as a suffix?`

124
Q

Which 2 functional groups are the only ones with a space in their name?

A

esters and amide

125
Q

Naming secondary/tertiary amides:

A

amine then carboxylic acid

126
Q

Naming primary amides:

A

carboxylic acid then amine

Chemistry 12 (4 decks)

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