1.3 The chemistry of carbon / hydrogen containing compounds Stoker Chp 1.3-1.8 ORGANIC CHEMISTRY 1.3 The chemistry of carbon / hydrogen containing compounds

HYDROCARBONS THE SIMPLEST TYPE OF ORGANIC COMPOUNDS Stoker Chp 1.3-1.8 HYDROCARBONS THE SIMPLEST TYPE OF ORGANIC COMPOUNDS HYDROCARBONS - CONTAIN ONLY C, H

Stoker Chp 1.3-1.8 HYDROCARBONS C H at least one triple bond ALKYNES

COMMON HYDROCARBON TYPES Stoker Chp 1.3-1.8 COMMON HYDROCARBON TYPES C H only single bonds Saturated hydrocarbons at least one double bond Unsaturated hydrocrabon at least one triple bond ALKYNES

HYDROCARBON DERIVATIVES Stoker Chp 1.3-1.8 HYDROCARBON DERIVATIVES One or more H’s are replaced with an atom of O, N, S, F, Cl, Br, I

HYDROCARBON DERIVATIVES Stoker Chp 1.3-1.8 HYDROCARBON DERIVATIVES C H Cl C H O C H OH

Saturated Hydrocarbons cont’d Stoker Chp 1.3-1.8 Saturated Hydrocarbons cont’d Fig. 1.2 Terms for organic compounds. 3-6)

1.4 Alkanes Acyclic (no rings) = alkane Cyclic (contains rings) Section 1.12 C H

1.4 Alkanes (cont.) Are acyclic “saturated” hydrocarbons. Contain only single bonds C-C Every carbon is sp3 (tetrahedral) General formula of alkanes is CnH2n+2 CH4 C2H6 C3H8

Stoker Chp 1.3-1.8 1.4 Alkanes Fig. 1.3 Molecular structures of (a) methane, (b) ethane, and (c) propane, the three simplest alkanes.

1.5 Structural formulas Expanded (Lewis structure) H H H H H H | | | | | | H-C-H H-C-C-H H-C-C-C-H Methane Ethane Propane THESE TAKE A LOT OF SPACE TO DRAW THEY TAKE A LONG TIME TO DRAW

1.5 Structural formulas Condensed (easier and faster to draw) Methane CH4 Ethane CH3-CH3 Propane CH3-CH2-CH3

1.5 Structural formulas Condensed Octane: CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH3 More condensed CH3-(CH2)6-CH3

1.6 Alkane Isomerism Linear carbon chain Octane: CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH3 Branched carbon chain (acyclic) CH3 | CH3-CH-CH2-CH2-CH2-CH2-CH3

CONSTITUTIONAL ISOMERISM Same molecular formula, different connectivity of the atoms As the #C increase the #isomers increases very rapidly (Table 1.1)

1.7 Conformations of alkanes Stoker Chp 1.3-1.8 1.7 Conformations of alkanes MOST ATOMS ATTACHED BY A SINGLE BOND ARE FREE TO ROTATE AROUND THE BOND The relative orientation of the atoms is called a CONFORMATION HOW MANY CONFORMATIONS ARE THERE?

CONFORMATIONS OF BUTANE Stoker Chp 1.3-1.8 CONFORMATIONS OF BUTANE SAWHORSE PROJECTIONS OF PREVIOUS SLIDE C H 3 SYN ANTI C C C C GAUCHE GAUCHE C C C C ECLIPSED ECLIPSED C C C C

I nternational U nion of P ure and A pplied C hemistry Stoker Chp 1.3-1.8 1. 8 IUPAC RULES systematic nomenclature I nternational U nion of P ure and A pplied C hemistry colloquially: “eye-you-pac”

FEATURES OF THE IUPAC SYSTEM Stoker Chp 1.3-1.8 FEATURES OF THE IUPAC SYSTEM It is a system where every compound (even isomers) has a unique name. If the rules are followed, everyone gets the same name for a given compound. Once given the name, anyone can draw the structure of the compound. WORKS BOTH DIRECTIONS IUPAC STRUCTURE NAME

1.2

IUPAC METHOD 1. Find the longest continuous chain of Stoker Chp 1.3-1.8 IUPAC METHOD 1. Find the longest continuous chain of carbon atoms and name it using the linear alkane names. 2. Number the chain starting from the end nearest a branch.

IUPAC METHOD 3. Give each substituent a name based on the Stoker Chp 1.3-1.8 IUPAC METHOD 3. Give each substituent a name based on the number of carbon atoms it has. 4. Give each substituent a locant number determined by its location on the chain. 5. Assemble the name.

RULE 1. FIND THE LONGEST CONTINUOUS CHAIN OF CARBON ATOMS AND NAME IT Stoker Chp 1.3-1.8 RULE 1. FIND THE LONGEST CONTINUOUS CHAIN OF CARBON ATOMS AND NAME IT C-C C-C-C-C-C-C-C-C-C C 9 it won’t always be the horizontal one as shown here NONANE all possibilites must be examined try these also …….. C-C C-C C-C-C- C-C-C-C-C-C C- C-C-C -C-C-C-C-C C C 6 8

RULE 2. Number the chain starting from the end nearest a branch Stoker Chp 1.3-1.8 RULE 2. Number the chain starting from the end nearest a branch nonane C-C 1 2 3 4 5 6 7 8 9 C-C-C-C-C-C-C-C-C C

Stoker Chp 1.3-1.8 RULE 3. Give each substituent a name based on the number of carbon atoms it has. substituent nonane C-C 1 2 3 4 5 6 7 8 9 C-C-C-C-C-C-C-C-C C substituent Groups attached to the main chain are called substituents.

methyl ethyl propyl butyl pentyl hexyl heptyl octyl nonyl decyl Stoker Chp 1.3-1.8 (substituents) methyl ethyl propyl butyl pentyl hexyl heptyl octyl nonyl decyl

Stoker Chp 1.3-1.8 RULE 3. Give each substituent a name based on the number of carbon atoms it has. ethyl nonane C-C 1 2 3 4 5 6 7 8 9 C-C-C-C-C-C-C-C-C C methyl

Rule 4. Give each substituent a locant number Stoker Chp 1.3-1.8 Rule 4. Give each substituent a locant number determined by its location on the chain. 4- ethyl nonane C-C 1 2 3 4 5 6 7 8 9 C-C-C-C-C-C-C-C-C C 2- methyl

RULE 5. Assemble the name. “ane” MAIN CHAIN STEM LOCANT SUBSTITUENT Stoker Chp 1.3-1.8 “ane” MAIN CHAIN STEM LOCANT SUBSTITUENT ENDING number word suffix word name of the substituent indicates the type of compound indicates position of the substituent on the chain indicates the number of carbon atoms in the chain

PUNCTUATION RULES 1. Numbers are separated from words by hyphens Stoker Chp 1.3-1.8 PUNCTUATION RULES 1. Numbers are separated from words by hyphens 2-methyl……. 2. Numbers are separated from numbers by commas. 2,3- …….. example coming shortly Substituents are named in alphabetical order ……4-ethyl-2-methyl…. 4. All words are joined - no breaks ……methylnonane

ASSEMBLING A NAME 4-ethyl-2-methylnonane 4-ethyl nonane C-C Stoker Chp 1.3-1.8 ASSEMBLING A NAME 4-ethyl nonane C-C 1 2 3 4 5 6 7 8 9 C-C-C-C-C-C-C-C-C C 2-methyl 4-ethyl-2-methylnonane

ORGANIC NOMENCLATURE 4 3 2 1 2-methylbutane butane 2- methyl Stoker Chp 1.3-1.8 ORGANIC NOMENCLATURE 4 3 2 1 butane 1. find longest chain and name 2- methyl 2. number from end nearest a branch 3. name substituents 2-methylbutane 4. locant number 5. assemble name

Stoker Chp 1.3-1.8 Name this compound 1 2 3 4 5

Stoker Chp 1.3-1.8 Name this compound 4 3 2 1 5 6 7

Use multipliers if there are MORE THAN ONE of the same substituent Stoker Chp 1.3-1.8 2345678910 DI- TRI- TETRA- PENTA- HEXA- HEPTA- OCTA- NONA- DECA- These are ignored when alphabetizing

How would you name this one? Stoker Chp 1.3-1.8 How would you name this one? Every substituent must get a number 1 2 3 4 5 6