AP CHEM Organic Chemistry Notes (Basic), Summaries of Chemistry

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Notes to Supplement --- Organic Chemistry
Chemistry I, and AP Chemistry
Mr. von Werder, WLHS
The Element Carbon
► The element carbon has properties that allow it to make up tens thousands of molecules, many of
which are essential to the existence of life.
Allotropes of carbon
Allotrope
different forms of the same element (as opposed to isotope… or isomer…)
due to different bonding patterns or arrangements
different forms usually have significantly different chemical and physical properties
Some of the more familiar carbon allotropes:
Diamond
Each carbon is bonded to four other carbons; tetrahedral geometry (see model)
Strong and stable arrangement of the bonds makes diamond very strong and hard.
Uses; ornamentation and jewelry, as tips on cutting tools, coatings
Graphite
Carbon atoms are bonded in sheet-like fashion (see model)
‘Sheets’ are weakly bonded to each other - slip over each other easily (lubricant)
Mixture of graphite and clay is used to make pencil “lead”
Amorphous carbon
Amorphous (“a” – without; “morph” – shape)
This form of carbon has no predictable arrangement of its atoms
Charcoal, soot, bone black, coke
Fullerenes
Globe shaped, cage like arrangements of carbon atoms (see model).
Also known as “buckyballs” (named geodesic dome engineer R. Buckminster Fuller)
Recently discovered (couple of decades ago); uses are still being researched.
Unique Bonding of Carbon
Carbon has four outermost (valence) electrons
Allows it to typically form four covalent bonds to achieve a stable octet of electrons
Carbons has a relatively small size its valence electrons are relatively close to the nucleus
This small size allows for short strong covalent bonds to form (single, double, triple)
Carbon can form long chains of carbon bonded to carbon, bonded to another carbon, etc.
These chains, with other atoms bonded here and there, allow carbon to be the backbone to
thousands of different molecules. (Examples…)
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Notes to Supplement --- Organic Chemistry

Chemistry I, and AP Chemistry Mr. von Werder, WLHS

The Element Carbon

► The element carbon has properties that allow it to make up tens thousands of molecules, many of which are essential to the existence of life.  Allotropes of carbon  Allotrope ◼ different forms of the same element (as opposed to isotope… or isomer…) ◼ due to different bonding patterns or arrangements ◼ different forms usually have significantly different chemical and physical properties  Some of the more familiar carbon allotropes: ◼ Diamond

  • Each carbon is bonded to four other carbons; tetrahedral geometry (see model)
  • Strong and stable arrangement of the bonds makes diamond very strong and hard.
  • Uses; ornamentation and jewelry, as tips on cutting tools, coatings ◼ Graphite
  • Carbon atoms are bonded in sheet-like fashion (see model)
  • ‘Sheets’ are weakly bonded to each other - slip over each other easily (lubricant)
  • Mixture of graphite and clay is used to make pencil “lead” ◼ Amorphous carbon
  • Amorphous (“a” – without; “morph” – shape)
  • This form of carbon has no predictable arrangement of its atoms
  • Charcoal, soot, bone black, coke ◼ Fullerenes
  • Globe shaped, cage like arrangements of carbon atoms (see model).
  • Also known as “buckyballs” (named geodesic dome engineer R. Buckminster Fuller)
  • Recently discovered (couple of decades ago); uses are still being researched.  Unique Bonding of Carbon  Carbon has four outermost (valence) electrons ◼ Allows it to typically form four covalent bonds to achieve a stable octet of electrons  Carbons has a relatively small size – its valence electrons are relatively close to the nucleus ◼ This small size allows for short strong covalent bonds to form (single, double, triple)  Carbon can form long chains of carbon bonded to carbon, bonded to another carbon, etc. ◼ These chains, with other atoms bonded here and there, allow carbon to be the backbone to thousands of different molecules. (Examples…)

Hydrocarbons

► Hydrocarbons – molecules that contain only hydrogen and carbon (surprise). ► These two elements alone can form thousands of different combinations  Properties of Hydrocarbons  Two types of bonds exist in hydrocarbons ◼ C-C; which is nonpolar ◼ C-H; which is essentially nonpolar ◼ This means that hydrocarbons as molecules are NONPOLAR MOLECULES  Being nonpolar give hydrocarbons certain properties: ◼ Nonconductors of electricity (rubber and plastics are good wire insulators) ◼ Low densities (tend to float on water… think of oil slicks, spills, candles) ◼ Low melting points, boiling points (tend to liquids and gases at room temp) ◼ Do not dissolve well in water (“oil and water don’t mix”; “like dissolves like”)  Find hydrocarbons in places away from possible interaction with oxygen and nitrogen in the air ◼ Underground, mostly in deposits of natural gas and petroleum

  • Fossil fuels is a term used because of the theory that they have formed from the compressed, decomposed remains of plants and animals from very long ago  Hydrocarbon Structures and Formulas  FORMULAS of hydrocarbons ◼ Molecular formula (Review - what was empirical formula?)
  • tells how many of each type of atom in the molecule
  • Examples: C 3 H 8 C 6 H 12 (Review - what are the empirical formulas?)
  • Drawback - no information about the arrangement, or bonding, of the atoms is given ◼ Structural formula
  • tells how the atoms in the molecule are bonded to each other, and the types of bonds
  • Examples:
  • Drawbacks - only two-dimensional
  • bond angles are not accurately represented
  • these can be cumbersome to write out ◼ Condensed structural formula
  • does not show each of the C-H bonds, but still usually shows the C-C bonds
  • this avoids some of the hassle of the structural formula, but still shows some bonding
  • Examples: CH 3 - CH 2 - CH 3 CH 3 - CH 2 - CH 2 - CH=CH-CH 3
  • This is the form that we will use in writing formulas for organic molecules. ◼ Carbon skeleton
  • shows only the carbon atoms and their bonds C—C—C C—C—C—C═C—C ◼ Line structure
  • Shows only the bonds between carbons (each bend in the line represents a carbon)

H H H

H C C C H

H H H

H H H H

H C C C C C C H

H H H H H H

CH 3 - CH 2 - CH 2 - CH 3

Conformations and Structural Isomers ◼ Conformations● just a “different look” at the same molecule

  • On paper it is just the result of writing the structural formula differently.
  • In reality it is due to the rotations of C-C bonds.
  • But, all are the same compound with the same properties… same name. ◼ Structural isomers
  • Compounds that have the same molecular formula , but different structural formulas.
  • “iso” – same; “mer” - part
  • For example: C 4 H 10 butane 2 - methylpropane Both have the same molecular formula, but they are different structural formulas.
  • Draw all the possible isomers for C 6 H 14 , and then name them.  Cycloalkanes ◼ Hydrocarbons can also form rings – cycloalkanes ◼ Various ring structures are possible, but the most stable are at about five or six carbons ◼ Notice that for a ring to form there are two less hydrogens. ◼ Naming simple ring structures just requires putting cyclo- as a prefix to the alkane name ◼ Note that from a 3-D view, or from a model, that cyclohexane has two possible conformations: “boat” - less stable “chair” - more stable and found more often in many other organic molecules  Unsaturated Hydrocarbons  Unsaturated hydrocarbons – Not filled to capacity with hydrogens Due to presence of a double or triple bond(s)  ALKANES - organics with all single bonds
  • saturated – filled to capacity with hydrogens
  • have the general formula CnH2n+  ALKENES - hydrocarbons with one or more double bonds
  • unsaturated – because two hydrogens have to be lost to form the double bond
  • have the general formula CnH2n
  • Naming alkenes: Use the same root name but use an – ene suffix Number the carbons (mentally); identify where the double bond is
  • Ethene (common: ethylene); used in making plastics
  • Propene (common: propylene); also used in making plastics
  • Note: The double bond prevents rotation around that C=C bond Allows for another type of isomer – geometric isomer (cis-, trans- forms)  ALKYNES - hydrocarbons with one or more triple bonds
  • unsaturated – also because less than the maximum number of hydrogens
  • have the general formula CnH2n- 2
  • Naming alkynes: Use the same root name but use an – yne suffix Number the carbons (mentally); identify where the triple bond is (Demo: Flash in the Pan)
  • Ethene (common: acetylene); used in oxyacetylene torches for welding

CH 3

CH 3 - CH-CH 3

Benzene ◼ Benzene is stable arrangement of six carbons in a ring, with 6 hydrogens ◼ August Kekule came up with the structure of benzene based on a dream he had… ◼ There are 6 electrons are shared equally in the ring of six carbons (delocalized bonding)

  • This delocalized bonding makes the structure more stable and less reactive
  • The circle inside the hexagon better represents the delocalized bonding
  • Often, we just draw the benzene ring (hexagon/circle); the hydrogens are understood. ◼ Aromatic compounds – those organic compounds that contain the benzene ring ◼ Naming compounds with benzene rings is done two ways: 1. If simple branches come off the benzene ring , “benzene” serves as the root word. Numbers indicate the position of branches if there is more than one Disubstituted benzenes – two branches off benzene ring
  • three possible positions for the two branches
  • numbers are the preferred way of designating the branches
  • However, traditionally prefixes of ortho-, meta-, and para- have also been used.
  • Examples: paradichlorobenzene (alternative to naphthalene mothballs)
  • On the lighter side, consider these:
  1. If the benzene ring is a branch off a much longer HC chain then we use the prefix “phenyl” to represent the benzene ring.

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

ortho - o -

meta - m -

para - p - PhD PhD PhD PhD

CH 3 – CH–CH 2 – CH–CH 2 – CH 2 – CH 2 – CH–CH 3 CH 3 CH 2 – CH 3

R - X

R - OH

R – O – R

Classes of Organic Compounds

Halocarbons, Alcohols, and Ethers

► Hydrocarbons are plentiful, but when you start considering these hydrocarbons with some simple substitutions there are even more compounds to consider. ► Here we will consider some of the main categories of organic compounds beyond hydrocarbons. We will learn to recognize each category and learn to name several of them. Functional Groups – an atom or group of atoms that has a characteristic chemical behavior (function)  Halocarbons  One or more of the hydrogens in a hydrocarbon has been replaced by a halogen(s)  Recall: halogens are group 17 on the periodic table (F, Cl, Br. I) X = F, Br, Cl or I  NAMING halocarbons

  • Name the halogens as branches off the main carbon chain
  • The halogens are prefixes (fluoro-, chloro-, bromo-, iodo-) to the hydrocarbon name
  • Use numbers to indicate the halogen position(s) ◼ Examples:  Common examples/uses of halocarbons
  • CFCs; chlorofluorocarbons; used as a refrigerants ➢ Being phased out in some applications; replaced with HFCs; hydrofluorocarbons
  • CCl 4 ; tetrachloromethane (common: carbon tetrachloride); ➢ Was a dry cleaning solvent (however, toxic and suspected carcinogen) ➢ Being replaced with dichloromethane
  • DDT; largely used as a pesticide decades ago; but use was banned in the U.S. in 1972 ➢ http://www.chem.ox.ac.uk/mom/ddt/ddt.html
  • Used as intermediates in chemical reactions.  Alcohols  One or more of the hydrogens in a hydrocarbon has been replaced by a hydroxyl group (- OH )  Note: the – OH group here does not dissociate in water; so is chemically different than the hydroxide ion (OH-)  The – OH group in alcohols makes them reasonable polar in small molecules (up to 4 carbons), and so they dissolve well in water. (Why not longer chained alcohols?)  NAMING alcohols – we’ll stick to the simple ones.
  • Drop the “ e ” from the end of the hydrocarbon chain and add “- ol
  • If necessary, provide the lowest number for the position of the – OH group ◼ Examples:  Common examples/uses of alcohols
  • Methanol (common: methyl alcohol) ➢ Used to “denature” ethanol; “poisons” the ethanol making it unfit to drink. Why do that?
  • Ethanol (common: ethyl alcohol, grain alcohol) ➢ The “alcohol” in alcoholic beverages – the intoxicating substance ➢ Naturally produced through fermentation of glucose
  • 2 - propanol (common: isopropyl alcohol, rubbing alcohol) ➢ Used as a base for perfumes, creams, lotions, etc.
  • 1,2-ethandiol (common: ethylene glycol) ➢ Used mainly in antifreeze
  • 1,2,3-propantriol (common: glycerol) ➢ Used also as base in soaps, cosmetics, foods, pharmaceuticals…look for it.  Ethers  Ether – compound in which an oxygen atom bonded to two carbon atoms  NAMING ethers – I’m not holding you to it.

O

  • C –

R – NH 2

Aldehydes and Ketones

 Carbonyl group - carbon atom is double bonded to an oxygen atom

  • found in aldehydes and ketones  Aldehydes  Organic molecules with a carbonyl group at the end of the carbon chain  NAMING aldehydes – I’m not holding you to it.  Methanal (common: formaldehyde) has been used to preserve biological specimens  Ketones  Organic molecules with a carbonyl group not at the end of the carbon chain.  NAMING ketones – I’m not holding you to it.  Propanone (common: acetone) is commonly used as a solvent; nail polish remover

Carboxylic Acids and Esters

 Carboxyl group

  • carbon atom is double bonded to an oxygen AND single bonded to a hydroxyl group
  • found in carboxylic acids and in a slightly modified form in esters  Carboxylic Acids  Organic molecules with a carboxyl group (must be at the end of the carbon chain)  NAMING carboxylic acids – we’ll stick to the simple ones.
  • Drop the “ e ” from the end of the hydrocarbon chain and add “- oic acid ”  Methanoic acid (common: formic acid) first extracted from ants  Ethanoic acid (common: acetic acid); the acid in vinegar  The carboxyl group is an important part of amino acidsEsters  Organic molecules with a “carboxyl group” having the H replaced with more carbon(s)  NAMING esters – we’ll try to stick to the simple ones.
  • The carbon branch bonded to the oxygen is named first (e.g. methyl… )
  • Then drop the “ e ” from the end of the hydrocarbon chain and add “- oate ”  Esters are formed by the reaction of an alcohol and a carboxylic acid (Lab).  Many have pleasant odors and are natural and synthetic fragrances and flavors.

Amines and Amides

 Nitrogen forms a couple of notable functional groups:

  • Amines; containing an amino group (-NH 2 )
  • Amides  Amines  Organic molecules with an amino group  NAMING amines – I’m not holding you to it.  The amino group is an important part of amino acids  Amides  Organic molecules with an amino group attached to the carbon of a carbonyl group  NAMING amides – I’m not holding you to it.  The amide bond (peptide bond) is the result of amino acids linking together.

O

R – C – H

O

R – C – R’

O

R – C – OH

O

R – C – O-R’

O

H-N C C O-H

H H

O

H-N C C O-H

H H

O

R – C – NH 2

O

H-N C C

H H

O

N C C O-H + H 2 O

H H

O

H-N C C O-H +

H H

O

H-N C C O-H

H H