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Chemistry 30 > Unit 2: Organic Chemistry > Flashcards

Unit 2: Organic Chemistry Flashcards

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1
Q

What is organic chemistry?

A

The study of molecular carbon compounds. Does not include carbonates, cyanides, and oxides.

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2
Q

What is special about carbon?

A

Carbon has 4 bonding electrons allowing it to create numerous and varied compounds.

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3
Q

What shapes can carbon compounds make?

A

Chains, rings, spheres, and tubes.

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4
Q

IUPAC organic naming prefixes.In order from least to greatest.

A

Meth, eth, prop, but, penta, hexa, hepta, octa, nona, deca.

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5
Q

What is the structure of a IUPAC name?

A

Prefix-parent-infix-suffix.
The prefix is the substituents of the compound.
The parent is how many carbon atoms are in the main backbone.
The infix refers to the number of multiple bonds in the main backbone.
The suffix refers to the family that it belongs to. (Alkanes, alkenes, alkynes)

There are additional parts. Cyclo refers to a ring.
Substituents are preceded by their location, and sorted alphabetically (including their prefix).
If halogens are included, they have their ending replaced with o. (Bromine to bromo) and have numerical prefixes stating their location.

Trans and cis refer to whether the groups of interest are on the opposite side of the double bond, or the same side.

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6
Q

What are hydrocarbons made of?

A

Carbon and hydrogen. If some of the hydrogen is replaced by other atoms, it is a derivative or hydrocarbons.

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7
Q

What is the carbon backbone?

A

The longest chain in a hydrocarbon molecule.

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8
Q

What is an alkane?

A

The simplest of organic compound families.
Chains of carbon atoms connected by single bonds.
Formula is Cn H(2n+2)

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9
Q

What is a saturated organic compound?

A

Alkanes. The bonding electrons are minimally used for carbon bonds. Remaining electrons are bonded to hydrogen atoms.

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10
Q

What is a line diagram?

A

Each point of the zigzag is a carbon atom. Hydrogen atoms are not drawn. It is a zigzag. Parts of the line may be a double or triple line depending on the bonds between carbon atoms.

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11
Q

What is a condensed formula?

A

Ex. Hexane. CH3CH2CH2CH2CH2CH3.
Butene. CH2CH1CH2CH3
Propyne. CHCCH3

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12
Q

How do you determine the numbers used for naming organic compounds?

A

Find the longest carbon chain (the backbone) and determine the side which results in the lowest numbers. Remember that double or triple bonds take precedence over substituents when numbering.

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13
Q

What is a structural formula?

A

Shows atomic symbols and the bonds between them (aside from Hydrogen). For example, Butene is C=C-C-C

1-Bromo ethane is Br-C-C

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14
Q

Alkenes are what?

A

Hydrocarbons that have carbon-carbon double bond(s). Formula is C(n) H(2n).

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15
Q

Alkene naming?

A

Prefix for number of carbon atoms, followed by 1 number for where the double bond(s) exist. If more than one bond exists, the family name needs a prefix as well.
Example. C=C=C-C is but-1,2-biene
C-C-C-C-C=C-C-C is oct-3-ene

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16
Q

Alkyne naming?

A

Same as alkenes but family part of names uses yne instead of ene.

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17
Q

What are alkynes?

A

Same as alkanes and alkenes but with a triple carbon bond. Formula is C(n)H(2n-2)

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18
Q

What do you need to remember about alkyne line diagrams?

A

Bonds on either side of the triple bond are straight (no rotation)

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19
Q

What is a cycloaliphatic?

A

Alkanes, alkenes, and alkynes, are all aliphatics and can exist in rings.

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20
Q

Cycloaliphatics naming?

A

Cyclo prefix is used before the carbon backbone name.
Ex. 1,2,4 trimethyl CYCLOhexane (do not actually capitalize like this)

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21
Q

What is an isomer?

A

When two or more compounds have the SAME CHEMICAL FORMULA but DIFFERENT ARRANGEMENT OF ATOMS and different physical properties, they are called isomers. There are two types, stereoisomers and structural isomers.

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22
Q

What is a structuralisomer?

A

Molecules with the same formula are bonded together in different orders and have different names. For example, Pent-1-ene and pent-2-ene are structuralisomers. (Remember that there is no Pent-3-ene because it is the same as pent-2-ene).

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23
Q

What is a stereoisomer?

A

Same molecular formula (and sort of the same names). They only occur in organic compounds with double bonds.

Naming: When groups of interest (any atoms that are not hydrogen) are on the same side, prefix with cis (cis = same). When they are on the opposite side, use trans (trans=opposite).
For example, but-2-ene can have the CH3s on the end on the same side of the double bond, or the opposite side. Cis-but-2-ene compared to trans-but-2-ene.

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24
Q

Why did the food industry like to use transfats?

A

Transfats have trans orientations, giving them lower melting points and extending their shelf-life. This was ideal for things such as margarine (which would use transfats) compared to butter.

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25
Q

What is a functional group?

A

A specific group of atoms within a molecule that affects the properties of the compound. Multiple bonds are considered a functional group and alter the compounds properties.

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26
Q

What type of bond is stronger/weaker? Between single and double or triple bonds.

A

Double and triple bonds are weaker than single bonds and can break to create free bonding electrons to bond with other elements or functional groups.

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27
Q

What is hydrogenation?

A

When an alkene or alkyne combines with hydrogen to form an alkane. (To saturate a compound)

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28
Q

What is halogenation?

A

When an alkene or alkyne combines with an element from the halogen family (group 7A)

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29
Q

When a hydrohalide combines with a hydrocarbon, what rule does it follow?

A

Markovnikov’s rule which states: the hydrogen will bond to the carbon atom in the double bond that has the most hydrogen already bonded to it. The halogen bonds to the other carbon.

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30
Q

What is hydration?

A

When an alkene or alkyne combines with water. The water molecule breaks into a single hydrogen and hydroxyl group (OH). Follow Markovnikov’s rule if applicable.

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31
Q

What are hydrocarbons with a hydroxyl group known as?

A

Alcohols

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32
Q

How do additional double bonds affect naming

A

You add a prefix to the suffix

Ex. Pent-1,2-diene

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33
Q

How does an aliphatic forming a ring affect naming

A

Cyclo goes before the parent
Ex. Cyclopentene

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34
Q

Naming alcohols

A

ol is suffix

Example, OH-C-C is ethanol
C-C-C with OH attached to second carbon is propan-2-ol

If more than one OH present, prefix the family name and add ol
Ex. 2 OH; diol
Use numbers between suffix and family name
Ex C-C-C with OH one first and second, is propan1,2diol

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35
Q

What does IUPAC stand for?

A

International Union of Practical Applied Chemists

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36
Q

How do you name the substituents of an organic compound?

A

find how many of each compound exist (to find their prefix) then sort alphabetically (including prefix). Find the side from which to start iterating through the carbon chain by determining which side will result in the lowest numbers (prioritising lower numbers for double or triple bonds in alkanes or alkynes respectively). They follow the structure of #, #… - {number of same substituents prefix}{type of substituent ending in yl}

For example, if CH3 is attatched twice on the first atom and once on the third of a carbon backbone, 1,1,3-trimethyl

Example 2. CH2=CH-CH-CH3 with ethyl attatched to the CH connected to CH3… 3-ethyl but-1-ene (1 in butene is optional)

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37
Q

Can organic compounds be molecular or ionic?

A

Organic chemistry is the study of molecular carbon compounds. Electrons are shared

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38
Q

What is a derivative of hydrocarbons?

A

A hydrocarbon in which some or all of the hydrogen atoms have been replaced by other atoms

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39
Q

What is a substituent group?

A

Groups of atoms off the main chain

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40
Q

2 compounds with the same chemical formula but different order of atoms and different physical properties are what

A

Structural isomers

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41
Q

2 compounds with the same formula and order but differ in 3d-orientation of atoms in space are what

A

Stereoisomers

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42
Q

What is trans fat?

A

Fats are just long hydrocarbon chains that can be saturated. Trans fats are fats that are in a trans orientation. Fat can also be saturated to achieve the same effects.

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43
Q

Is trans fat or fat natural?

A

Fat is natural.

Trans fat is not found in nature. It is made by hydrogenating fat (adding hydrogen)

44
Q

How would you represent the addition of organic compounds?

A

Draw the two compounds in their structural diagram with an addition sign between them. Instead of an equals sign, use an arrow pointing towards the product (another structural diagram)

45
Q

What is hydrohalogenation?

A

When an alkene or alkyne combines with a hydrogen halide.

This follows Markovnikov’a rule if applicable

46
Q

Do isomers have different names?

A

Structural isomers have different names, but stereoisomers do not (unless using cis or trans)

47
Q

What is an aromatic?

A

An unsaturated hydrocarbon that has a ring structure and pattern that make it stable

48
Q

What is benzene?

A

A 2D carbon ring with three double and three single bonds, but all bonds are shared equally

49
Q

What is phenyl?

A

Benzene as a substituent

50
Q

What is a benzene substituent called?

A

Phenyl

51
Q

How do you name an aromatic?

A

With benzene as the parent, #-substituents benzene

For example, a benzene with one methyl attached is 1-methylbenzene

When benzene is a substituent (phenyl) name as an alkane/ene/yne but with phenyl as a substituent

52
Q

What is an alcohol?

A

Hydrocarbons with the hydroxyl functional group (OH)

53
Q

How do you determine the degree of an alcohol?

A

By how many carbons are bonded to the carbon containing the hydroxyl group.
1-primary or 1 degree
2-secondary or 2 degree
3-tertiary or 3 degree

54
Q

How are alcohols made?

A

Fermenting sugar with yeast and addition reactions with water

55
Q

What are ethers?

A

An organic compound containing an oxygen atom between two carbons in a chain.

56
Q

How do you name ethers?

A

Add the suffix -oxy to the smaller hydrocarbon group that is bonded to the larger.
Ex. C-C-O-C is methoxyethane
C-C-C-O-C-C-C-C is propoxybutane

57
Q

What is an aldehyde?

A

a carbonyl (C=O) group bonded to only 1 carbon (end of a chain)

58
Q

How do you name aldehydes?

A

Drop the -e from the name of the parent molecule and add the suffix -al. Position numbers are not used because the carbonyl group is always designated as 1 on the chain.
Ex. C-C-C-C-C=O with methyl attached to the second carbon (in order of text) is 4-methylpentanal

59
Q

What is a ketone?

A

A carbonyl group (C=O) bonded to 2 other carbon atom (middle of chain).

60
Q

How do you name ketones?

A

Drop the -e suffix from the parent molecule and add the suffix -one. For ketones with 5 or more atoms, the position of the carbonyl group is denoted with an infix.
Ex. C-C-C-C-C-C-C with O double bonded to the 6th carbon, the name is heptan-2-one

61
Q

What is a carboxylic acid?

A

A weak organic acid that contains the functional group, carboxyl (COOH) Carboxyl is a carbon atom double bonded to oxygen and single bonded to hydroxide, leaving a free electron. Carboxyl combines the carbonyl and hydroxyl groups.

62
Q

How do you name carboxylic acids?

A

Start with the longest chain containing carboxyl. Drop the -e from the parent molecule and add the suffix -oic followed by the word acid.
Ex. C-C-COOH is propanoic acid

63
Q

What is an ester?

A

A carboxylic acid but the hydrogen atom of the hydroxyl group (OH) is replaced with an alkyl group (carbon chain). They have alcohol and carboxylic acids. The alcohol is attached to the single-bonded oxygen and the carboxylic acid is attached to the double bonded oxygen.

64
Q

How do you name esters?

A

Take the alcohol part and name it like a substituent with the same number of carbons (pentanol becomes pentyl). Take the name of the carboxylic acid and change the ending from -oic to -oate and drop the acid word.
Ex. C-C-C-C(=O)-O-C-C-C-C-C is pentyl butanoate

65
Q

What are fats and oils?

A

Large ester molecules known as liptids. The long-chain carboxylic acid is called a fatty acid. The alcohol component is glycerol.

66
Q

What is an amine?

A

A hydrocarbon that includes an amino group in its structure. A derivative of ammonia (NH3) where one of the hydrogen atoms is replaced with a carbon chain. They can exist as parent molecules or substituents.

67
Q

How do you name amines as substituents?

A

drop the -e at the end of the parent molecule and replace it with -amine. The position of the amino group is denoted with an infix (numbering takes priority over other substituents, but not carboxyl, and not over multiple bonds).
Ex. C=C-C-NH2 is propen-3-amine
C-C-(-NH2)-C-C is butan-2-amine.

68
Q

How do you name amines as parent molecules?

A

When ammonia replaces 2 or more of its hydrogen atoms with carbon chains, it becomes a parent molecule. Name the carbons as substituent groups. Ex. 2 methane chains on ammonia is dimethylamine (numbering provide no information, as there are only 3 spots to fill AROUND the ammonia)

69
Q

What is an amino acid?

A

An amino group and an acid group (carboxylic acid).

70
Q

How do you name alcohols?

A

Drop the -e from the parent hydrocarbon and add the suffix ol. Used numbers to signify where the hydroxyl group is.
Ex. CH3-CH(-OH)-CH3 is propan-2-ol

C-C-C with hydroxyl groups on all carbon atoms would be propan-1,2,3-triol

71
Q

What is an ether?

A

An organic compound containing oxygen between 2 carbons in a chain. R-O-R

72
Q

How do you name ethers?

A

Add the oxy suffix (replacing e) to the smaller carbon chain that is bonded to the larger. Then add the larger carbon chain.
Ex: C-C-O-C-C-C is ethoxypropane

73
Q

What is the most widely accepted explanation of the origin of fossil fuels?

A

Formed from dead and decaying plant and animal matter

74
Q

What is natural gas?

A

Primarily methane, but contains impurities that make it “sour” like hydrogen sulfide.

75
Q

How does fracking work?

A

Hydraulic fracturing. Water, sand, and other chemicals are forced into a well at very high pressure. This creates cracks that form in the rock and release natural gas.

76
Q

What are some concerns of fracking?

A

High water consumption, water contamination, high pollution, links to seismic activity.

77
Q

What is the most valuable natural gas?

A

Methane. Followed by ethane.

78
Q

What is ethane cracking?

A

Removing two hydrogen atoms from ethane to create ethene.

79
Q

What is crude oil?

A

A mixture of hundreds and even thousands of different compounds.

80
Q

What is fractional distillation?

A

Heats crude oil to take advantage of the different boiling points of the various chemicals to separate them.

81
Q

What is a polymer?

A

Large numbers of simple molecules (monomers) are joined in a repeating pattern to form a chain. These chains bind together.

82
Q

Properties of alcohols.

A

Higher melting and boiling points than a hydrocarbon would without a hydroxyl.
More soluble in water than alkanes and alkenes.
The Hydroxyl group is polar while the hydrocarbon chain is not polar, so alcohols dissolve polar and non-polar compounds (like dissolves like).
Alcohols are regularly used as industrial solvents.

83
Q

Aldehyde and ketone properties.

A

Due to the carbonyl group.
The carbonyl oxygen is more electronegative, therefore attracts electrons from the carbon and makes aldehydes and ketones polar.
More polar than hydrocarbons, but less than alcohol (alcohol uses hydrogen bonds making them quite strong).
Smaller aldehydes and ketones are completely soluble in water, but larger ones are not (larger ones act more non-polar as carbon chains become larger).
Often used as industrial processes as solvents.

84
Q

Carboxylic acid properties.

A

Two polar groups, carbonyl and hydroxyl, are located close together, making them very polar. Carboxyl groups form hydrogen bonds with one another. Readily dissolve in water and alcohol. Share many properties with other acids (react with metals to produce hydrogen gas). Neutralizes bases.

85
Q

Properties of fat.

A

Insoluble in water. Liptids (long ester molecules) are non-polar by the nature of long fatty acid chains. Saturated fats contain single-carbon bonds and can be packed tightly, increases the Vans der Waals forces between the molecules and makes them more difficult to break, making them more likely to be solid at room temperature.

86
Q

What is a saturated fat?

A

A fat with only single bonds between the carbon atoms.

87
Q

What is a monounsaturated fat?

A

A fat with one double bond between the carbon atoms.

88
Q

With is a polyunsaturated fat? *

A

A fat with more than 2 double bonds between the carbon atoms.

89
Q

Properties of amines.

A

Because of the lone pair electrons on the amino group, amines are polar and are soluble in water. If an amino group is acting as a substituent, its solubility will decrease as the carbon chain becomes longer Ex: Heptanamine is less soluble than propanamine.

90
Q

What are the building blocks of protein?

A

Amino acids.

91
Q

Is carbon more likely to share electrons or take/give them?

A

Share them. Covalent bonds are more likely.

92
Q

Does methene exist?

A

No. Methane consists of 1 carbon atom, for it to be an alkene there would need to be 2 carbon atoms to create a double bond (ethene)

93
Q

What is a monomer?

A

The building blocks that create polymers. The most simple one is ethene (double bonds break allowing new things to be added).

94
Q

What is a hydroxyl functional group?

A

C-OH

95
Q

R-CH=O functional group.

A

Aldehydes (end of chain)

96
Q

R-C(=O)-R functional group.

A

Ketones (middle of chain)

97
Q

C-O-C functional group.

A

Ether.

98
Q

R-O-C(=O)-R

A

Ester.

99
Q

Numbering priority.

A

Double/triple bonds, hydroxyl functional group, other substituents.

Carboxyl groups take priority over other substituents.

100
Q

What are some natural and synthetic polymers?

A

Natural: starches, cellulose, and proteins

Synthetic: all plastics, styrofoam, nylon, polyester, synthetic rubber, Kevlar, and resins

101
Q

Amino acid naming

A

Name as propanoic acid, with amino group as a substituent (ex: 3-amino,2-methylhexanoic acid)

102
Q

What did Michael Faraday do?

A

Isolated benzene from a mixture of oil

103
Q

Who isolated Benzene from oil?

A

Michael Faraday

104
Q

What are starches?

A

A naturally occurring polymer

105
Q

These compounds’ solubility decreases as they become longer

A

Aldehydes, ketones, amines, esters

106
Q

What functional group gives some things their scent?

A

Carbonyl; Aldehydes and ketones.
Carboxylic acids and esters can also give some things scent (carboxyl is carbonyl and hydroxyl)

Chemistry 30 (7 decks)

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