Naming Hydrocarbons
(nomenclature)
Drawing Structures: It’s All Good
CH3
C
H
C
H
CH3
CH3
CH3
CH3
CH
CH
CH3
2-butene
This is called the
“condensed structure”
...
Basic Naming of Hydrocarbons
Hydrocarbon names are based on: 1) type,
2) # of carbons, 3) side chain type and position
1) ...
Mnemonic for First Four Prefixes
First four prefixes
• Meth-
• Eth-
• Prop-
• But-
Monkeys
Eat
Peeled
Bananas
Decade
Decimal
Decathalon
Other Prefixes
• Pent-
• Oct-
• Dec-
• Hex-, Hept-, Non-
Quiz – On LL (5 min.; 12 pts)
1. What are the 3 classes of hydrocarbons, based on
number of carbon-carbon bonds?
2. Give t...
Numbering Carbons
Q- draw 1-pentene
A- Where’s the double
bond? We # C atoms.
• Naming compounds with multiple bonds is mo...
Quiz (LL, 3 min.)
1. Name the 4 groups of hydrocarbons
(alphabetically)
2. Draw the structures for the following
compounds...
CH3 CH3
CH3
CH3Naming Side Chains
• The names of molecules
with branches are based
on: side chains, root
• The “root” or “...
IUPAC Rules for Naming Hydrocarbons
1. Choose the correct ending: -ane, -ene, or -yne
2. Determine the longest carbon chai...
5. Determine the correct name for each branch
(“alkyl” groups include methyl, ethyl, propyl, etc.)
6. Attach the name of t...
ene
Naming Side Chains
Example: use the rules on this handout
to name the following structure
CH3 CH2 C
CH2
CH2 C
CH2
CH3
...
ene
Rule 2: determine the longest carbon chain
CH3 CH2 C
CH2
CH2 C
CH2
CH3
CH3
CH3
Naming Side Chains
Rule 3: Assign numbers to each carbon
CH3 CH2 C
CH2
CH2 C
CH2
CH3
CH3
CH3
ene
Naming Side Chains
Rule 3: Assign numbers to each carbon
CH3 CH2 C
2
CH2
1
CH2
3
C
4
CH2
5
CH3
CH3
CH3
6
CH3 CH2 C
CH2
CH2 C
CH2
CH3
CH3
CH3
...
1-hexeneene
Rule 4: attach prefix (according to # of Cs)
Naming Side Chains
CH3 CH2 C
2
CH2
1
CH2
3
C
4
CH2
5
CH3
CH3
CH3
...
CH3 CH2 C
2
CH2
1
CH2
3
C
4
CH2
5
CH3
CH3
CH3
6
Rule 5: Determine name for side chains
CH3 CH2 C
CH2
CH2 C
CH2
CH3
CH3
CH3...
CH3 CH2 C
CH2
CH2 C
CH2
CH3
CH3
CH3
CH3 CH2 C
2
CH2
1
CH2
3
C
4
CH2
5
CH3
CH3
CH3
6
1-hexene2-ethyl-4-methyl-4-methyl-1-he...
Rule 7,8: group similar branches
CH3 CH2 C
CH2
CH2 C
CH2
CH3
CH3
CH3
CH3 CH2 C
2
CH2
1
CH2
3
C
4
CH2
5
CH3
CH3
CH3
6
1-hex...
Rule 7,8: group similar branches
CH3 CH2 C
CH2
CH2 C
CH2
CH3
CH3
CH3
CH3 CH2 C
2
CH2
1
CH2
3
C
4
CH2
5
CH3
CH3
CH3
6
2-eth...
2-butene
propene
1-butyne
CH3 CH CH2
CH3 CH CH CH3
CH3 CH CH C
CH3 CH3
CH3
2,4-dimethyl-2-pentene
CH C CH2 CH3
b) same
c) 5-ethyl-4-methyl-2-heptyne
a) 3,3-dimethyl-1-pentene
CH2 CH C CH2 CH3
CH3
CH3
CH3 C CH CH2
CH3
CH2 CH3
CH CH CH...
Quiz – 12 points (LL, 5 min.)
We will be correcting this together.
Draw
• 3 – methyl-1,3-cyclopentene
• 2-ethyl-1-pentene
...
Isomers
Same molecular formula, different molecular structures.
Two types: structural and geometric isomers.
1. Structural...
Isomers (cont’d)
2. Geometric Isomers: differ only in the geometry of their
substituted groups.
cis- 2 - butene trans- 2 -...
Warm-Up
Work in pairs. You have 20 minutes to complete.
1. Draw the structural formulas: 3. Name the following:
a) 3-ethyl...
Isomers (cont’d)
Stereoisomers: molecules of the same molecular structure that
differ only in the arrangement of the atoms...
Isomers (cont’d)
Stereoisomers: molecules of the same molecular structure that
differ only in the arrangement of the atoms...
Isomers (cont’d)
Stereoisomers: molecules of the same molecular structure that
differ only in the arrangement of the atoms...
Isomers (cont’d)
Stereoisomers: molecules of the same molecular structure that
differ only in the arrangement of the atoms...
Aromatic Hydrocarbons
Aromatic hydrocarbons are hydrocarbons that have six-membered
carbon rings and delocalized electrons...
Isomers (cont’d)
Asymmetric Carbon: a carbon with four different groups attached to it.
C
F
Cl
BrH
Chlorofluorobromomethane
Functional Groups
• Besides our basic hydrocarbon classes, we can add
other elements/ions, groups of elements to an
organi...
Let’s practice
drawing and
naming!
Open text
to p. _____
Classes of Organic Compounds
A functional group gives an organic compound properties that are
very different from those of...
Classes of Organic Compounds (ctn’d)
2. Ethers: are organic compounds in which two hydrocarbon
groups are bonded to the sa...
Classes of Organic Compounds (ctn’d)
3. Aldehydes and ketones: contain the carbonyl group:
Aldehyde: organic compound in w...
Classes of Organic Compounds (ctn’d)
4. Carboxylic Acids: are organic compounds that contain the
carboxyl functional group...
Classes of Organic Compounds (ctn’d)
Many esters have distinctive fruit-like odors, which has led to their
commonplace use...
Let’s practice
drawing and
naming!
Open text
to p. _____
Hydrocarbon nomenclature
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Hydrocarbon nomenclature

  1. 1. Naming Hydrocarbons (nomenclature)
  2. 2. Drawing Structures: It’s All Good CH3 C H C H CH3 CH3 CH3 CH3 CH CH CH3 2-butene This is called the “condensed structure” C C C C H H H H H H H H CH3 CH CH CH3 On a test, choose a method that shows all Hs CH3CH=CHCH3 Using brackets can also shorten some formulas: CH3CH2CH2CH2CH2CH3 vs. CH3(CH2)4CH3
  3. 3. Basic Naming of Hydrocarbons Hydrocarbon names are based on: 1) type, 2) # of carbons, 3) side chain type and position 1) name will end in -ane, -ene, or -yne 2) the number of carbons is given by a “prefix” 1 meth- 2 eth- 3 prop- 4 but- 5 pent- 6 hex- 7 hept- 8 oct- 9 non- 10 dec- Actually, all end in a, but a is dropped when next to a vowel. E.g. a 6 C alkene is hexene Q - What names would be given to these: 7C, 9C alkane 2C, 4C alkyne 1C, 3C alkene heptane, nonane ethyne, butyne methene, propene
  4. 4. Mnemonic for First Four Prefixes First four prefixes • Meth- • Eth- • Prop- • But- Monkeys Eat Peeled Bananas
  5. 5. Decade Decimal Decathalon Other Prefixes • Pent- • Oct- • Dec- • Hex-, Hept-, Non-
  6. 6. Quiz – On LL (5 min.; 12 pts) 1. What are the 3 classes of hydrocarbons, based on number of carbon-carbon bonds? 2. Give the 10 organic homologous prefixes, in order, from 1-10. 3. Name these compounds: CH3 C H C H CH3 CH3 CH3 C2H4
  7. 7. Numbering Carbons Q- draw 1-pentene A- Where’s the double bond? We # C atoms. • Naming compounds with multiple bonds is more complex than previously indicated. • When 2+ possibilities exist, #s are needed. • Always give double bond the lowest number. • Q - Name these C C C CCH3 H H H H H H HCH3 1 C 2 C 3 C 4 C 5 H H H H H H HCH3 5 C 4 C 3 C 2 C 1 H H H H H H H 1-pentene C C CC C C CH3 H3 H H H H H HHH C C C H H H H
  8. 8. Quiz (LL, 3 min.) 1. Name the 4 groups of hydrocarbons (alphabetically) 2. Draw the structures for the following compounds: A. 2-octene B. 4-decyne C. hexane D. 3, 4, 5 – triethyldecane E. 2-chloro – 4 – methyl – nonane 3. When done, take homework out to review! Homework: Section Review 25.3 and 25.4 (notebook, show all work); read p. 762- 765; both on quiz tomorrow!
  9. 9. CH3 CH3 CH3 CH3Naming Side Chains • The names of molecules with branches are based on: side chains, root • The “root” or “parent chain” is usually the longest possible hydrocarbon chain. • The root must include multiple bonds if they are present. If a cyclic structure is present it will be the root even if it is not the longest chain. • Side chains are also called “side branches” or “alkyl groups”. Their names end in -yl. Common side chains : -CH3 methyl, -CH2CH3 ethyl, -CH2CH2CH3 propyl 2,3-dimethylpentane CH3 CH3 CH3 CH3
  10. 10. IUPAC Rules for Naming Hydrocarbons 1. Choose the correct ending: -ane, -ene, or -yne 2. Determine the longest carbon chain. Where a double or triple bond is present, choose the longest chain that includes this bond. If there is a cyclic structure present, the longest chain starts and stops within the cyclic structure. 3. Assign numbers to each C of the parent chain. For alkenes and alkynes the first carbon of the multiple bond should have the smallest number. For alkanes the first branch (or first point of difference) should have the lowest #. Carbons in a multiple bond must be numbered consecutively. 4. Attach a prefix that corresponds to the number of carbons in the parent chain. Add cyclo- to the prefix if it is a cyclic structure.
  11. 11. 5. Determine the correct name for each branch (“alkyl” groups include methyl, ethyl, propyl, etc.) 6. Attach the name of the branches alphabetically, along with their carbon position, to the front of the parent chain name. Separate numbers from letters with hyphens (e.g. 4-ethyl-2-methyldecane) 7. When two or more branches are identical, use prefixes (di-, tri-, etc.) (e.g. 2,4-dimethylhexane). Numbers are separated with commas. Prefixes are ignored when determining alphabetical order. (e.g. 2,3,5-trimethyl-4-propylheptane) 8. When identical groups are on the same carbon, repeat the number of this carbon in the name. (e.g. 2,2-dimethylhexane) IUPAC Rules for Naming Hydrocarbons
  12. 12. ene Naming Side Chains Example: use the rules on this handout to name the following structure CH3 CH2 C CH2 CH2 C CH2 CH3 CH3 CH3 Rule 1: choose the correct ending
  13. 13. ene Rule 2: determine the longest carbon chain CH3 CH2 C CH2 CH2 C CH2 CH3 CH3 CH3 Naming Side Chains
  14. 14. Rule 3: Assign numbers to each carbon CH3 CH2 C CH2 CH2 C CH2 CH3 CH3 CH3 ene Naming Side Chains
  15. 15. Rule 3: Assign numbers to each carbon CH3 CH2 C 2 CH2 1 CH2 3 C 4 CH2 5 CH3 CH3 CH3 6 CH3 CH2 C CH2 CH2 C CH2 CH3 CH3 CH3 ene Naming Side Chains
  16. 16. 1-hexeneene Rule 4: attach prefix (according to # of Cs) Naming Side Chains CH3 CH2 C 2 CH2 1 CH2 3 C 4 CH2 5 CH3 CH3 CH3 6 CH3 CH2 C CH2 CH2 C CH2 CH3 CH3 CH3
  17. 17. CH3 CH2 C 2 CH2 1 CH2 3 C 4 CH2 5 CH3 CH3 CH3 6 Rule 5: Determine name for side chains CH3 CH2 C CH2 CH2 C CH2 CH3 CH3 CH3 1-hexene1-hexene ethyl methyl methyl Naming Side Chains
  18. 18. CH3 CH2 C CH2 CH2 C CH2 CH3 CH3 CH3 CH3 CH2 C 2 CH2 1 CH2 3 C 4 CH2 5 CH3 CH3 CH3 6 1-hexene2-ethyl-4-methyl-4-methyl-1-hexene ethyl methyl methyl Rule 6: attach name of branches alphabetically Naming Side Chains
  19. 19. Rule 7,8: group similar branches CH3 CH2 C CH2 CH2 C CH2 CH3 CH3 CH3 CH3 CH2 C 2 CH2 1 CH2 3 C 4 CH2 5 CH3 CH3 CH3 6 1-hexene2-ethyl-4-methyl-4-methyl-1-hexene ethyl methyl methyl Naming Side Chains
  20. 20. Rule 7,8: group similar branches CH3 CH2 C CH2 CH2 C CH2 CH3 CH3 CH3 CH3 CH2 C 2 CH2 1 CH2 3 C 4 CH2 5 CH3 CH3 CH3 6 2-ethyl-4,4-dimethyl-1-hexene ethyl methyl methyl Naming Side Chains
  21. 21. 2-butene propene 1-butyne CH3 CH CH2 CH3 CH CH CH3 CH3 CH CH C CH3 CH3 CH3 2,4-dimethyl-2-pentene CH C CH2 CH3
  22. 22. b) same c) 5-ethyl-4-methyl-2-heptyne a) 3,3-dimethyl-1-pentene CH2 CH C CH2 CH3 CH3 CH3 CH3 C CH CH2 CH3 CH2 CH3 CH CH CH2 CH2 CH3 CC CH3CH3 CH3 For more lessons, visit www.chalkbored.com
  23. 23. Quiz – 12 points (LL, 5 min.) We will be correcting this together. Draw • 3 – methyl-1,3-cyclopentene • 2-ethyl-1-pentene Name: 3. 4. 5. Give both names! Homework: Concept Practice #28-43, in notebook (p. 768; show all work!)
  24. 24. Isomers Same molecular formula, different molecular structures. Two types: structural and geometric isomers. 1. Structural Isomers: molecules with same chemical formula, but different molecular structures. butane (C4H10) 2 – methylpropane (C4H10) CH3-CH2-CH2-CH3 CH3-CH-CH3 CH3
  25. 25. Isomers (cont’d) 2. Geometric Isomers: differ only in the geometry of their substituted groups. cis- 2 - butene trans- 2 - butene cis-configuration: substituted groups are on the same side as the double bond. trans-configuration: substituted groups are on the opposite sides of the double bond.
  26. 26. Warm-Up Work in pairs. You have 20 minutes to complete. 1. Draw the structural formulas: 3. Name the following: a) 3-ethyl-1,4-cyclopentene b) 1-chloro-2,3,4-triethyl-3-heptene C = C c) 2-fluoro-7,7-dimethyl-4-decyne 2. Draw the cis and trans forms of the C = C following alkenes: a) 2-pentene 4. Identify the asymmetric b) 2-octene carbon, if any: c) 2-methyl-2-heptene a) CH3CH2CHO d) 2,3-dimethyl-2-butene b) CH3CHOH H CH3 CH2CH2CH3 H CH3 CH3 CH3 CH3 CH3 a) b)
  27. 27. Isomers (cont’d) Stereoisomers: molecules of the same molecular structure that differ only in the arrangement of the atoms in space. They are mirror images of each other (think right and left hands.)
  28. 28. Isomers (cont’d) Stereoisomers: molecules of the same molecular structure that differ only in the arrangement of the atoms in space. They are mirror images of each other (think right and left hands.) Left-handed (S)
  29. 29. Isomers (cont’d) Stereoisomers: molecules of the same molecular structure that differ only in the arrangement of the atoms in space. They are mirror images of each other (think right and left hands.) Left-handed (S) Right-handed (R)
  30. 30. Isomers (cont’d) Stereoisomers: molecules of the same molecular structure that differ only in the arrangement of the atoms in space. They are mirror images of each other (think right and left hands.) “left-handed” “right-handed”
  31. 31. Aromatic Hydrocarbons Aromatic hydrocarbons are hydrocarbons that have six-membered carbon rings and delocalized electrons. Benzene is the primary aromatic hydrocarbon. Benzene has the chemical formula C6H6 and can also be thought of as 1,3,5-cyclohexatriene (hexene). Benzene can also be represented graphically like this.
  32. 32. Isomers (cont’d) Asymmetric Carbon: a carbon with four different groups attached to it. C F Cl BrH Chlorofluorobromomethane
  33. 33. Functional Groups • Besides our basic hydrocarbon classes, we can add other elements/ions, groups of elements to an organic structure = Functional Groups • R = radical or, in this case, represents C • Alcohols (R-OH), ethers (R-O-R), carboxylic acids (R-COOH), aldehydes (R-COH) – what are the others presented in the book? • Identifying these! • Naming these (all have their own endings)!
  34. 34. Let’s practice drawing and naming! Open text to p. _____
  35. 35. Classes of Organic Compounds A functional group gives an organic compound properties that are very different from those of corresponding hydrocarbons. Some examples: 1. Alcohols: are organic compounds that contain one or more hydroxyl groups. The general formula for alcohols is R-OH (rememeber that “R” stands for the rest of the molecule.) Glycerol: 1,2,3-propanetriol Ethanol: 1-ethanol
  36. 36. Classes of Organic Compounds (ctn’d) 2. Ethers: are organic compounds in which two hydrocarbon groups are bonded to the same oxygen atom. This can can be represented by the formula R-O-R. Diethyl Ether: Dioxane: Dimethyl Ether:
  37. 37. Classes of Organic Compounds (ctn’d) 3. Aldehydes and ketones: contain the carbonyl group: Aldehyde: organic compound in which the carbonyl group is attached to a carbon atom at the end of a carbon chain. Ketone: organic compound in which the carbonyl group is attached to carbon atoms within the chain. Aldehyde Ketone
  38. 38. Classes of Organic Compounds (ctn’d) 4. Carboxylic Acids: are organic compounds that contain the carboxyl functional group. A member of this class of organic compounds can be represented by the general formula: 5. Esters: are organic compounds that have carboxylic acid groups in which the hydrogen of the hydroxyl group has been replaced by an alkyl group. Observe:
  39. 39. Classes of Organic Compounds (ctn’d) Many esters have distinctive fruit-like odors, which has led to their commonplace use in artificial flavorings and fragrances. Examples:
  40. 40. Let’s practice drawing and naming! Open text to p. _____
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