Ch10 Stuff

Why are there so many organic compounds?

carbon form stable, covalent bonds with other carbon atoms. carbon can form up to 4 covalent bonds with other carbon

Carbon atoms form stable bonds with other elements, such as:

oxygen, nitrogen, sulfur, halogen, the presence of these other elements confers many new physical and chemical properties on organic compound

Carbon atoms form double or triple bonds with other atoms to produce

a variety of structures with differing properties

What kind of bonds are these

double bonds

What kind of bonds are these

triple bonds

What are some ways to arrange carbon and other atoms?

branched chains, ring structures, and linear chains

Differences between organic and inorganic compounds:

Bond type

organics have covalent bonds (electron sharing), inorganics usually have ionic bonds (electron transfer)

Differences between organic and inorganic compounds:

structure

Organic: molecules, nonelectrolytes. Inorganics: three dimensional crystal structures, often water soluble, dissociating into ions-electrolytes

Differences between organic and inorganic compounds:

Physical Differences, Melting Point and Boiling Point

organics have lower melting points, intermolecular forces are broken fairly easily. Inorganics usually have higher melting points, ionic bonds require more energy to break

Differences between organic and inorganic compounds:

Physical Differences, Water solubility

organics are nonpolar, water insoluble. Inorganics are water-soluble, readily dissociate

What do hydrocarbons contain

only carbon and hydrogen

What kind of molecules are hydrocarbons

nonpolar, not soluble in water

What are hydrocarbons soluble in

typical nonpolar organic solvents, ex: toluene and pentane

What are hydrocarbons constructed of

chains or rings of carbon atoms with sufficient hydrogen atoms to fulfill carbons need for four bonds

What do substituted hydrocarbons have

at least one hydrogen atom that is replaced by another atom or group of atoms

contain only single bonds, for example: ethane, CH₃CH₃

alkanes

Alkanes with carbon atoms bonded in rings

cycloalkanes

Contain at least one double bond, for example, ethene

alkenes

contain at least one triple bond, for example, ethyne

alkynes

Alkanes are

compounds that contain only carbon-carbon and carbon-hydrogen single bonds

A saturated hydrocarbon has no

double or triple bonds

Alkenes and alkynes unsaturated hydrocarbons because

they contain at least one carbon to carbon double or triple bond

saturated hydrocabron

unsaturated hydrocarbon

Cyclic structure of hydrocarbons

form a closed ring

Aromatic hydrocarbons contain a

benzene ring or related structure

cycloalkane/cyclohexane

an aromatic hydrocarbon/benzene

general formula for a chain alkane is

C_nH_2n+2

C_nH_2n+2

What is n

the number of carbon atoms in the molecule

Are alkanes saturated hydrocarbons

yes, they contain only carbon and hydrogen. Bonds are carbon-hydrogen and carbon-carbon single bonds

Molecular formula

C₂H₆ , C₃H₈

lists kind and number of each type of atom in a molecule, no bonding pattern

Structural formula

shows each atom and bond in a molecule

Condensed formula

shows all the atoms in a molecule in sequential order indicating which atoms are bonded to which

Skeletal Structure

assumes a carbon atom at any location where lines intersect, each carbon in the structure is bonded to the correct number of hydrogen atoms

Alkanes molecular formula

CnH2n+2

Methane molecular formula

CH4

Ethane molecular ethane

C2H6

Propane molecular formula

C3H8

Butane molecular formula

C4H10

Pentane molecular formula

C5H12

Hexane molecular formula

C6H14

Heptane molecular formula

C7H16

Octane molecular formula

C8H18

Nonane molecular formula

C9H20

Decane molecular formula

C10H22

Methane condensed formula

CH4

Ethane condensed formula

CH3CH3

Propane condensed formula

CH3CH2CH3

Butane condensed formula

CH3CH2CH2CH3 or CH3(CH2)2CH3

Pentane condensed formula

CH3CH2CH2CH2CH3 or CH3(CH2)3CH3

Hexane condensed formula

CH3CH2CH2CH2CH2CH3 or CH3 (CH2 )4CH3

Heptane condensed formula

CH3CH2CH2CH2CH2CH2CH3 or CH3 (CH2 )5CH3

Octane condensed formula

CH3CH2CH2CH2CH2CH2CH2CH3 or CH3 (CH2 )6CH3

Nonane condensed formula

CH3CH2CH2CH2CH2CH2CH2CH2CH3 or CH3 (CH2)7CH3

Decane condensed formula

CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3 or CH3(CH2)8CH3

Many carbon compounds exist in the form of

isomers

Isomers are

compounds with the same molecular formula but different structurees

Physical properties of hydrocarbons

nonpolar molecules, not water soluble; soluble in nonpolar organic solvents, low melting points and low boiling point, generally less dense (lighter) than water, as length (molecular weight) increases melting and boiling points increase as does the densitity

primary carbon

secondary carbon

tertiary carbon

An ___ ___ is an alkane with one hydrogen atom removed. It is named by replacing the -ane of the alkane name with -yl

alkyl group

Ethyl groups, using ethane as the example

for ethane, all 6 H’s are equivalent. Removing one H generates the ethyl group

Alkyl Group Structure:

-CH₃

Methyl

Alkyl Group Structure:

-CH₂CH₃

ethyl

Alkyl Group Structure:

-CH₂CH₂CH₃

propyl

Alkyl Group Structure:

-CH₂CH₂CH₂CH₃

Butyl

Alkyl Group Structure:

-CH₂CH₂CH₂CH₂CH₃

Pentyl

How are alkyl groups classified

According to the number of carbons attached to the carbon atom that joins the alkyl group to a molecule. All continuous chain alkyl groups are 1 degree. Isopropyl and sec-butyl are 2-degree groups

Iso- Alkyl Groups

Propane gives two propyl groups, depending on whether an end (1 degree) or interior (2 degrees) H is removed

Sec- Alkyl Groups

Butane gives two butyl groups, depending on whether an end (1 degree) or interior (2 degrees) H is removed

1. Classification:

2. Common name:

3. IUPAC Name:

1. secondary 2. Isopropyl 3. 1-Methylethyl

1. Classification:

2. Common name:

3. IUPAC Name:

1. primary 2. Isobutyl 3. 2-Methylpropyl

1. Classification:

2. Common name:

3. IUPAC Name:

1. secondary 2. sec-buytl 3. 1-methylpropyl

1. Classification:

2. Common name:

3. IUPAC Name:

1. tertiary 2. t-Butyl or tert-butyl 3. 1,1- Dimethylethyl

IUPAC

international union of pure and applied chemistry

Carbon chain length: 1

prefix and alkane name

meth-, methane

Carbon chain length: 2

prefix and alkane name

eth-, ethane

Carbon chain length: 3

prefix and alkane name

prop-, propane

Carbon chain length: 4

prefix and alkane name

but-, butane

Carbon chain length: 5

prefix and alkane name

pent-, pentane

Carbon chain length: 6

prefix and alkane name

hex-, hexane

Carbon chain length: 7

prefix and alkane name

hept-, heptane

Carbon chain length: 8

prefix and alkane name

oct-, octane

Carbon chain length: 9

prefix and alkane name

non-, nonane

Carbon chain length: 10

prefix and alkane name

dec-, decane

IUPAC Names for Alkanes, Rule One

The base or parent name for an alkane is determined by the longest chain of carbon atoms in the formula. The longest chain may bend and twist. Any carbon groups not part of the base chain are called branches or substituents. These carbon groups are also called alkyl groups

What is the longest chain in the molecule

8 carbon chain, octane

What is the longest chain in the molecule

7 carbon chain, heptane

IUPAC Names for Alkanes, Rule 2

Number the carbon atoms in the chain starting from the end with the first branch. If both branches are equally from the ends, continue until a point of difference occurs

IUPAC Names for Alkanes, Rule 3

Write each of the branches/substituents in alphabetical order before the base/stem name (longest chain). Halogens usually come first, indicating the position of the branch on the main chain by prefixing its name with the carbon number to which it is attached. Separate numbers and letters with a hyphen. Separate two or more numbers with commas.

When naming alkanes, what do you do when a branch/substituent occurs more than once

Prefix the name with di, tri, or tetra, then list the number of the carbon branch for that substituent to the name with a separate number for each occurrence. Separate numbers with commas

cycloalkanes have

two less hydrogens than the corresponding chain alkane

to name cycloalkanes, prefix clyco- to the name of the corresponding alkane

place substituents in alphabetical order before the base name name as for alkanes. For multiple substituents, use the lowest possible set of numbers, a single substituent requires no number

what cycloalkane structure is this

structural formula cyclopropane

what cycloalkane structure is this

cyclopropane line formula

what cycloalkane structure is this

cyclobutane structural formula

what cycloalkane structure is this

cyclobutane line formula

what cycloalkane structure is this

cyclohexane structural formula