OChem Ch 11

alcohol

-OH hydroxyl group

heteroatoms are _______electronegative than carbon, so they pull electron density away from carbon, making it partially positive and the heteroatom partially negative

more

condensed structure

most often used for compound having a chain of atoms bonded together, rather than a ring - all of the atoms are drawn in, but the two electron bond lines are generally omitted - lone pairs on heteroatoms are omitted Start at left side of molecule and remember that carbon atoms must have 4 bonds C bonded to 3 H's CH3, C bonded to 2 H's CH2, C bonded to 1 H becomes CH

amine

-NH2 amino group

Hydroxyl group

-OH

ether

-OR alkoxy group

thiol group

-SH sulfhydryl group

alkyl halide

-X halo group

Steps to determine shape around an atom

1) Draw in all the lone pairs around the heteroatom (needs 8 e's around it) 2) count groups to determine molecular shape

difference between ionic compounds and organic compounds

Organic compounds exist as discrete molecules with much weaker intermolecular forces - the forces that exist between molecules - than those seen in ionic compounds, which are held together by very strong interactions of oppositely charged ions

Drawing a tetrahedral

Solid line used for bonds in plane Wedge used for bond in front of plan Dashed line used for bond behind plane

How can we predict the shape around an atom in an organic molecule?

The shape around an atom is determined by counting groups and then arranging them to keep them as far away from each other as possible

VSEPR theory

Valence Shell Electron Pair Repulsion Theory based on the fact that electron pairs repel each other, thus, the most stable arrangement keeps these groups as far away from each other as possible

Functional groups contain a C atom singly bonded to a heteroatom

alkyl halides, alchohols, ethers, amines, and thiols

What is a functional group and why are they important?

an atom or a group of atoms with characteristic chemical and physical properties a functional group determines all of the properties of a molecule - it's shape, physical properties, and type of reaction it undergoes

Functional group

an atom or a group of atoms with characteristic chemical and physical properties it contains a heteroatom, a multiple bond, or sometimes both. determines molecules shape, properties, and type of reactions it undergoes. it behaves the same whether is is bonded to a C backbone having as few as two or as many as 20 C's.

heteroatom

any atom that is not carbon or hydrogen Most common are: N, O, and halogens (F, Cl, Br, and I) each heteroatom forms a characterisitic number of bonds determined by location in periodic table common heteroatoms also have nonbonding, lone pairs of electrons, so that each atom is surrounded by 8 electrons

caffeine

bitter tasting stimulant found in coffee, tea, cola beverages, and chocolate

capsaicin

compound responsible for characteristic spiciness of hot peppers, is the active ingredient in several topical creams for pain relief

carbonyl group

compounds containing a C=O double bond aldehydes, ketones, carboxylic acids, esters, and amides the type of atom bonded to the carbonyl carbon - hydrogen, carbon, or a heteroatom, determines the specific class of carbonyl compound

hydrocarbons

compounds that contain only elements of carbon and hydrogen - all except alkanes contain multiple bonds.

Aromatic compound

contain a benzene ring, a six-membered ring with three double bonds

carboxylic acid

contains an OH group bonded directly to carbonyl atom

ester

contains an OR group bonded directly to the carbonyl atom

Group

either a lone pair or a atom

aldehyde

has a H atom bonded directly to carbonyl atom

Are organic compounds polar or non-polar?

it depends. the polarity is determined by two factors: 1. the polarity of individual bonds 2. overall shape of molecule the polarity of an individual bonds depends on the electronegativity of the atoms that form it.

organic compounds have much ____________melting points and boiling points than ionic compounds

lower Ionic compounds are generally solids at room temp, many organic compounds are liquids and some even gases

methane

main component of natural gas, burns in presence of oxygen

In contrast, when an organic compound contains a single polar bond, as in the alkyl halide CH3CH2Cl, the molecule contains a ___________________, and is therefore a _____________ molecule

net dipole, polar molecule

Which organic compounds that have more than one polar bond, the shape of the molecule determines the overall polarity If the individual bond dipoles cancel in a molecule, the molecule is ___________________. If the individual bond dipoles do not cancel, the molecule is _______________________.

non-polar polar

Solubility: "Like dissolves like" Most organic compounds are soluble in _______________solvents Hydrocarbons and are non-polar solvents (are/are not) solvent in water Polar organic compounds are water soluble only if they are small, less then ____ carbons AND contain a ___or ___ atom that can hydrogen bond with water

organic are not soluble in water 6 carbons, N or O atom that can H bond with water

amide

organic compound obtained by replacing the −OH group in acids by the −NH 2 group

vitamins

organic compounds needed in small amts for normal cell function. our bodies cannot synthesize these compounds so they must be obtained in our diet. Most identified by a letter such as A, C, D, E, and K. Several different B vitamins so a subscript is used

MTBE

small polar organic molecule that has been used as a high octane additive in unleaded gasoline, use of which now caused environmental concerns because it's water soluble and has contaminated water supplies

organic chemistry

study of components that contain the element carbon clothes, foods, meds, gasoline, refrigerants, soaps are composed almost solely of organic compounds cotton, wool, silk - naturally occurring, can be isolated directly from natural sources nylon, polyester - synthetic, produced by chemists in lab

Skeletal structures

used for organic compounds containing both rings and chains of atoms 1. assume there is a carbon atom at the junction of any two lines or at the end of any line 2. assume there are enough H's around each carbon to give it 4 bonds 3. Draw in all heteroatoms and the H's bonded directly to them "cyclo"

4,4'-Dichlorobiphenyl (one of a group of compounds called PCB's)

used for the manufacture of polystyrene coffee cups and other products. Released into environment during production, use, storage, disposal and one of the most widely spready organic pollutants. Insoluble in water but very soluble in organic media so they are soluble in fatty tissue Ingesting large quantities of fish contaminated with PCBs has been shown to retard growth and memory retention in children

electronegativity symbol given to less negative atom

usually C or H

electronegativity symbol given to more electronegative atom

usually N, O, or a halogen

What shorthand methods are used to draw organic molecules?

In condensed structures, atoms are drawn in but the two electron bonds are generally omitted. Lone pairs are omitted as well. Parentheses are used around like groups bonded together or to the same atom. Three assumptions are used in drawing skeletal structures: 1) There is one carbon at the intersection of 2 lines or the end of any line 2) each carbon has enough hydrogens to give it 4 bonds 3) heteroatoms and the hydrogens bonded to them are drawn in

Inorganic Compound NaCL Bonding: Physical State: Boiling point: Solubility in water: Solubility in organic solvent: Flammability:

Inorganic Compounds NaCL Bonding: ionic Physical State: solid at room temp Boiling point: high (1413 C) Melting point: high (801 C) Solubility in water: soluble Solubility in organic solvent: insoluble Flammability: nonflammable

Alkenes

C-C double bond as functional group ex. ethylene

Most common functional groups can be subdivided into three types

1. hydrocarbons 2. compounds containing a single bond to a heteroatom 3. compounds containing a C=O group

linear carbon

2 groups 2 atoms 0 lone pairs 180 degrees

Trigonal planar carbon

3 groups 3 atoms 0 lone pairs 120 degrees

bent shape

4 groups 2 atoms 2 lone pairs 109.5 degrees

trigonal pyramidal

4 groups 3 atoms 1 lone pair bond angle 112 degrees

tetrahedral carbon

4 groups 4 atoms 0 lone pairs 109.5 degrees

When is a covalent bond non-polar?

A covalent bond is nonpolar when two atoms of identical or similar electronegativity are joined together. Thus, C-C and C-H bonds are nonpolar bonds.

What are vitamins and when is a vitamin fat-soluble or water soluble?

A vitamin is an organic compound that cannot be synthesized by the body but is needed in small amts for cell function. Fat soluble vitamin has many nonpolar C-C and C-H bonds and few polar bonds, making it insoluble in water. Water soluble vitamin has many polar bonds, so it dissolves in water.

Vitamin C aka ascorbic acid

A vitamin which humans are unable to synthesize and must obtain from diet, important in the formation of collagen, a protein that forms the connective tissues of skin, muscle, and blood vessels. deficiency causes scurvy. 6 C atoms and 6 O atoms - water soluble - dissolves in urine - soluble in gastric juices of stomach and blood

Fat-soluble vitamins

A, D, E, K Dissolves in an organic solvent but insoluble in water. Have many nonpolar C-C and C-H bonds and few polar functional groups

R --- Functional group

Abbreviation for carbon and hydrogen portion of the molecule - bonded to a particular functional group

carbon - 4 hydrogen - 1

All organic compounds contain carbon atoms and most contain hydrogen atoms. Carbon always forms ___ covalent bonds and hydrogen forms ____ covalent bonds.

Water-soluble vitamins

B and C dissolves in water. Has many polar bonds

Why are their so many organic compounds?

Because carbon forms 4 strong bonds with itself and other elements. Carbon atoms combine together to form rings and chains

Alkanes

C-C single bonds, no functional group ex. ethane alkanes have no functional groups and therefore no reactive sites are notoriously unreactive. For ex, polyethylene is a synthetic plastic and high molecular weight which consist of long chains of CH2 groups hundreds or thousands of atoms long. Stable compounds that does not easily degrade and thus remains in landfills

Alkyne

C-C triple bond as functional group ex. Acetylene

alcohols

Compounds that contain a -OH group are called...

What are characteristic features of organic compounds?

Contain C atoms and most contain H atoms. CC forms 4 bonds C forms single, double, and triple bonds to itself and other atoms Carbon atoms can bond to form chains or rings Organic compounds often contain heteroatoms, commonly N, O, and halogens

How do organic compounds differ from ionic inorganic compounds?

Main differences is their bonding. Organic compounds are composed of discrete molecules with covalent bonds. Ionic inorganic compounds are composed of cations and anions held together by the strong attraction of oppositely charged ions.

What are the solubility properties of organic compounds?

Most organic molecules are soluble in organic solvents Hydrocarbons and other nonpolar organic molecules are not soluble in water Polar organic molecules are water soluble only if they are small (less than 6 C's) and contain N or O atom that can hydrogen bond with water.

Hydrocarbons contain only C-C and C-H bonds which are _______________________, so hydrocarbons are ___________________ molecules

NON-POLAR

4

Number of bonds + Number lone pairs = ?

Hydrogen bonding patterns

Number of bonds: 1 Number of lone pairs: 0

Halogen bonding patterns

Number of bonds: 1 Number of lone pairs: 3 X = F, Cl, Br, I

Oxygen bonding patterns

Number of bonds: 2 Number of lone pairs: 2

Nitrogen bonding patterns

Number of bonds: 3 Number of lone pairs: 1

Carbon bonding patterns

Number of bonds: 4 Number of lone pairs: 0

Organic Compounds CH3CH2CH2CH3 Bonding: Physical State: Boiling point: Melting point Solubility in water: Solubility in organic solvent: Flammability:

Organic Compounds CH3CH2CH2CH3 Bonding: covalent Physical State: gas at room temp Boiling point: Low (-0.5 C) Melting point: Low (-138 C) Solubility in water: insoluble Solubility in organic solvent: Soluble Flammability: Flammable

4

a C atom surrounded by for atoms forms _______ single bonds.

double

a C atom surrounded by three atoms forms one ___________bonds.

triple

a C atom surrounded by two atoms generally forms one ___________bond.

When is a covalent bond polar?

a covalent bond is polar when atoms of different electronegativity are joined together. Thus bonds between carbon and common heteroatoms (N, O, and halogens) are polar bonds

How can we determine if an organic molecule is polar or nonpolar?

a nonpolar molecule has either no polar bonds or two or more bond dipoles that cancel a polar molecule has either one polar bond, or two or more bond dipoles that do not cancel

Vitamin A aka retinol

a vitamin which is a n essential component of the vision receptors in the eyes, and helps maintain the health of mucous membranes and the skin (many anti-aging creams contain it) deficiency leads to loss of night vision 20 carbons and single OH atom - water insoluble - soluble in any organic medium - readily stored in fat cells (liver) which are composed of organic compounds having C-C and C-H bonds

ethanol

alcohol; present in wine and other alcoholic beverages; formed by fermentation of sugar or made in lab by completely different process

Types of hydrocarbon compounds

alkanes alkenes alkynes aromatic compounds

rings or chains

carbon compounds can form either _______ or __________.

single, double and triple bonds to other carbon atoms

carbon forms ________, ________, and __________ bonds to other carbon atoms.

ketone

compound containing a carbonyl group =C=O bonded to two hydrocarbon groups