Honors Chemistry
Unit 8A
Organic Chemistry
 Allotropes
 Isomers
 Hydrocarbons
o Alkanes
o Alkenes
o Alkynes
o Aromatics
 Alkyl Halides
1
We are learning to:
1.
2.
Draw, model and name the hydrocarbon families
Recognize isomers of hydrocarbons
We are looking for:
1. a. Given a name, draw the structural formula for Alkanes, Cycloalkanes,
Alkenes, Cycloalkenes, Alkynes, Cycloalkynes, aromatics.
b. Given a structural formula, write the name for Alkanes, Cycloalkanes,
Alkenes, Cycloalkenes, Alkynes, Cycloalkynes, aromatics.
c. Given a model, write the name for Alkanes, Cycloalkanes, Alkenes,
Cycloalkenes, Alkynes, Cycloalkynes, aromatics.
2. Draw and name isomers of given hydrocarbon
2
3
4
5
Parent Chain/Carbon Number Prefixes:
Methane
CH4
Ethane
C2H6
Propane
C3H8
Butane
C4H10
Pentane
C5H12
Hexane
C6H14
Heptane
C7H16
Octane
C8H18
Nonane
C9H20
Decane
C10H22
Undecane
C11H24
Dodecane
C12H26
Branches will have one less hydrogen than parent chain formulas given above
all prefixes can be made into branches by replacing the –ane ending with–yl.
Methyl
CH3
Ethyl
C2H5
6
Introduction of parent chain and branches:
Place a box around the parent chain (longest continuous chain of carbons; it does not
have to be in a straight line)
1)
C—C—C—C—C
|
C
3)
C—C—C—C—C—C—C
|
C
|
C
5)
C—C—C
|
C—C—C—C—C—C—C
|
C
|
C
2)
4)
6)
C—C—C—C—C—C—C
| |
C C
|
C
C—C—C—C—C—C—C
|
|
|
C
C
C—C
|
C
C—C—C
|
C—C—C—C―C
|
C—C—C—C—C—C—C―C
|
C—C―C
|
C
7
Organic Chemistry
 Hydrocarbons contain Carbon and Hydrogen only
 If all bonds on the carbons are single bondsdrocarbon
Alkanes



Have form CnH2n+2 (where n = # of carbons)
Ending of the name is “ane”
Name
Molecular
Structural Formula
Model
Formula
CnH2n+2
Methane
Ethane
Propane
ISOMERS!!
Butane
2-Methylpropane
Basic Rules for Naming:
1) Identify the parent chain and number the carbons so the branches will have the lowest
combination of numbers.
2) Name the branches (use –yl ending) in alphabetical order and put the number of its position in
front of the branch name. These are written in front of the parent chain name.
3) Put dashes (-) between numbers and letters.
8
Example 1:
Draw
3-ethylheptane
Example 2:
Draw
2,7-dimethylnonane
Example 3:
Draw
4-ethyl-2,4,5-trimethyloctane
Example 4:
Draw
3,3,4,4-tetraethyl-2,2,5,5-tetramethylhexane
Cycloalkanes



All single bonds
Have form CnH2n
Ends of chain bond together (lose 2 hydrogens)
Examples:
Draw
cyclobutane
9
Draw 1,3-dimethylcyclopentane
Draw 1-ethyl-3-methyl-2-propylcyclobutane
More practice Naming Alkanes
1)
3)
C—C—C—C—C—C—C
|
C
|
C
2)
C—C—C—C
|
C
|
C
|
C—C—C
|
C
C
|
C—C—C—C—C—C—C
| | |
C C C
|
C
10
Unsaturated Hydrocarbons = not
all carbons have 4 single bonds (double
or triple bonds)
Alkenes


Structure contains double bonds
Have form CnH2n
Name
Molecular
Structural Formula
Model
Formula
CnH2n
Ethene
Propene
2-Butene
Drawing and naming Alkene structures: (parent chain must include the double bond;
number the parent chain to give the double bond the lowest number)
11
Alkynes

Structure contains triple bonds

Have form CnH2n-2
Name
Molecular Formula
Structural Formula
CnH2n-2
Ethyne
1-Propyne
1-Butyne
Naming and drawing Alkynes:
12
Aromatic Hydrocarbons
Mu
st contain at least one benzene ring

Naming Aromatics (when benzene is a branch, the branch is called phenyl )
13
Name ______________________________________________
Alkane Worksheet
Based on the given IUPAC name, give the structural formula for each of the following
molecules (number the carbons):
Name
Structural Formula
1.
dodecane
2.
2-methylheptane
3.
2,3,4-trimethylhexane
4.
3-methylpentane
5.
3-ethyl-2,4,4-trimethylnonane
6.
1-butyl,2,4-diethyl-3-methyl cyclobutane
14
Give the IUPAC name for each of the following molecules (number the carbons):
Name
Structural Formula
1.
CH3-CH2-CH2-CH2-CH2-CH2-CH3
2.
CH3

CH3-CH-CH2-CH3
3.
CH3
CH3 CH3

 
CH3-CH-CH2-CH-CH-CH3
4.
CH2-CH3

CH3
5.
6.
CH3
CH3


CH2
CH2


CH3-CH2-CH-CH2-CH2-CH-CH2-CH3
CH3
CH3
CH3



CH2 CH2
CH2



CH3-CH-CH-CH2-CH2-CH-CH2-CH3
15
Introduce Isomers:
Using C6H14, how many different ways can you arrange the 6 carbon atoms to form different
compounds? Remember, if they are different, they should have different names.
16
Name _____________________________________________
Draw and NAME the 18 isomers of Octane
Octane:
1.
Methyl heptane:
1.
2.
3.
Dimethyl hexane:
1.
2.
3.
4.
5.
6.
17
Ethyl hexane:
1.
Trimethyl pentane:
1.
2.
3.
4.
Ethyl methyl pentane:
1.
2.
Tetramethyl butane:
1.
18
Name ______________________________________________
Alkene Alkyne Assignment
Based on the given IUPAC name, give the structural formula for each of the following molecules
(number the carbons):
Name
Structural Formula
1.
3-heptene
2.
3-methyl-butyne
3.
4,5,5-trimethyl-1-hexene
4.
3-ethyl-2,4-dimethyl-2-pentene
5.
5-methyl-1,3-hexadiyne
6.
1,2,4-trimethyl-1-cyclopentene
7.
2,4,5-trimethyl-1,3-cyclohexadiene
19
Give the IUPAC name for each of the following molecules (number the carbons):
Name
Structural Formula
1.
C–C–C=C-C-C
2.
C

C=C–C–C-C
3.
C
C


C-C-C - C-C=C
4.
5.
6.
C
C–C-C
C
C


C
C


C ―C = C – C = C ―C – C
C C
 
C C C
  
CΞC-C - C-C -C≡C
7.
C
C ―C
20
Alkyl Halides:
 Organic compound with
 General Formula
o
o
o
o
–
–
–
–
 Naming:
o
Name as if the halogen is a branch
Examples:
21
Alkane, Alkene, Alkyne, Cyclos and Aromatic Review Sheet
Section 1: Draw the following structures:
1. 1-ethyl-2-methyl-cyclohexane
2. 2,3-dimethyl-1,5-heptadiene
3. 3-bromo-4,5-dichloro-6-iodo-undecane
4. 1-butyl-3-propyl-benzene
5. 3.3.4-trifluoro-1,6-octadiyne
6. 1-ethyl-4-methyl-1,3-cycloctadiene
7. 1-bromo-5,6-dichloro-3-fluoro-2,4-dimethyl-benzene
22
Section 2: Name the following structures
C
|
C—C—C=C
|
F
1) __________________________________
2) ___________________________________
3) ___________________________________
C―C
C
C
C
|
|
C—C—C—C—C—C—C―C
|
C
|
C
4) ___________________________________
Br
F
5) ___________________________________
6) ________________________________________
C
Cl
I
|
|
CΞC—C—CΞC—C―C
|
I
C=C
C
C―C―C
|
|
C― C ― C―C
| |
C C
|
C
7)___________________________________________
C—C—C—C—C—C—C―C―C―C―C
| | |
|
C C C
C
23
Information on Doing an “I-Search” Paper to Make-Up a Missed Organic Chem Modeling Lab:
1. An "I-Search” paper is telling the story of what you did in your search, those happenings and facts
crucial to your hunt for information on your assigned topic (the topic is the same as the topic for
the modeling lab that you missed).
You are to write 150 words (one page) for each modeling lab you miss.
2. The paper is to be typed and divided into three parts (each section is to be titled as below):
a. What I knew before I started my search.
b. The facts I found in my search and what I learned (include uses).
c. What I found the most interesting with what I learned.
3. If your make-up paper does not answer these questions, the best score you can receive
is half credit.
______________________________________________________________________________________________
Honors Chemistry
"Organic Chemistry Modeling Labs"
Alkanes – Straight and Branched
(2 points, ½ point each)
Grade/Initials
_______________ 1. hexane
_______________ 2. 3-methylpentane
_______________ 3. 2, 4-dimethylhexane
_______________ 4. 2, 2-dimethylpentane
_______________/2 Total points for Straight and Branched Alkanes
______________________________________________________________________________________________
Isomerism
(2 points, ½ point each)
Grade/Initials:
_______________ 1. butane isomer #1
(simple)
(0.25 point)
name _____________________________________
(0.25 point)
_______________ 2. butane isomer #2
(one branch) (0.25 point)
name _____________________________________
(0.25 point)
_______________ 3. pentane isomer #2
(one branch) (0.25 point)
name _____________________________________
(0.25 point)
_______________ 4. pentane isomer #3
(two branches) (0.25 point)
______________/2 Total points for Isomerism
name _____________________________________
(0.25 point)
24
Unsaturated Hydrocarbons
(3 points, ½ point each)
Grade/Initials
_______________ 1. 1-butene
_______________ 2.
2-butyne
_______________ 3.
2-methylpropene
_______________ 4.
3-methylbutene
_______________ 5.
1, 3-pentadiene
_______________ 6.
4-methylpentyne
_____________ /3 Total points for Unsaturated Hydrocarbons
_______________________________________________________________________________________________________
Mixed Aromatic Hydrocarbons, Alkyl Halides and Hydrocarbons
(3 points, ½ point each)
Grade/Initials
_______________ 1. 2-chloropropane
_______________ 2.
2-bromo-3,4 -dichloropentene
_______________ 3.
5-bromo-1- chloro-4,4-diiodo-5-methyl-2- hexyne
_______________ 4.
ethylbenzene
_______________ 5.
1-ethyl-3-methylbenzene
_______________ 6.
1,2,4-trimethylbenzene
_____________ /3 Total points for Aromatics and Alkyl Halides
_________________________________________________________________________________
Mixed Hydrocarbons
_______________ 1. 2, 3, 4-trimethylhexane
_______________ 2. propylcyclobutane
_______________ 3. Methylbenzene
_______________ 4. 1,1-difluoro-2-butyne
_______________ 5. 1-iodo-2-methylpropene
_______________ 6. 1, 3-pentadiene
_______________ 7. 3-bromo-1-chlorobutyne
_______________ 8. 1-chloro-2-ethyl-3fluoro-cyclohexene
_______________/ 4 Total points for Mixed Hydrocarbon
25
26
Honors Chemistry
Unit 8B
Organic Chemistry continued
 Alcohols
 Ethers
 Aldehydes
 Ketones
 Carboxylic acids
 Esters
 Amines
27
We are learning to:
1. Draw, model and name the hydrocarbon families.
2. Recognize isomers of hydrocarbons.
3. Draw, model and name the functional groups
We are looking for:
1 & 3 a. Given a name, draw the structural formula for Alkanes, Cycloalkanes,
Alkenes, Cycloalkenes, Alkynes, Cycloalkynes, aromatics, alkyl halides,
alcohol, ether, aldehydes, ketones, carboxylic acids, esters, and amines.
b. Given a structural formula, write the name for Alkanes, Cycloalkanes, Alkenes,
Cycloalkenes, Alkynes, Cycloalkynes, aromatics, alkyl halides, alcohol, ether,
aldehydes, ketones, carboxylic acids, esters, and amines.
c. Given a model, write the name for Alkanes, Cycloalkanes, Alkenes,
Cycloalkenes, Alkynes, Cycloalkynes, aromatics, alkyl halides, alcohol, ether,
aldehydes, ketones, carboxylic acids, esters, and amines.
2. Draw and name isomers of given hydrocarbon
28
Other Organic Compounds
 Functional Group –
 Same Functional Group
o
o
-
Alcohols:
 Organic compound that
 General Formula
 Naming:
o
If no number is present in front of the name – presume the –OH is on carbon number 1.
o
If 1 -OH group
 -
Examples:
o
If two or more -OH groups
 2=
 3=
 4=
 Keep the ane; add the appropriate ending listed above:
Examples:
29
Ethers:

Organic compounds

General Formula:
- R and R’
 Naming:
o–
o–
o–
Examples:
30
Name__________________________________________
Other Organic Compounds – WS I
Draw the following compounds (number the parent chain and circle any branches):
1) 1,8 nonanediol
4) dibutyl ether
2) 1, 3, 5 trimethylbenzene
5) 4-decanol
7) 1,2dibromo -1-chloroethane
3) 2-bromo-2-fluoro propane
6) 1-iodocyclobutane
8) 4-ethyl -3,6-difluoro-5-propyl-1-cyclohexene
9) 2,3-dichloro-7,8,9-triiodo-6,7,8-tripropyl-4-dodecene
10) 1,2,3,4,5,6-hexafluoro-1-hexanol
11) Decyl octyl ether
31
32
Other Organic Compounds (Continued)
Carbonyl group is a carbon double bonded to an oxygen, C=O
Aldehydes:
 Organic compounds
O

R–C–H
 General Form:
 Naming:
Example
O

C-C-H
lanthte
Ketones:
 Organic compounds
 General Form:
O

R – C – R’
 Naming:
Example:
O

C–C-C
2-propanone
33
Carboxylic Acids:
Carboxyl group is a carbon double bonded to an oxygen and single bonded to an oxygen with
hydrogen (-OH group)
O

- C – OH
 Organic compounds
O

 General Form:
R – C - OH
 Naming
o If one carboxyl group
-
o If more than one carboxyl group
 For 2 = dioic acid
Example:
O

O

OH – C – C – C – C – OH
1,4-butanedioic acid
34
Name__________________________________________
Other Organic Compounds – WS II
Draw the following compounds (number the parent chain and circle any branches):
1) 1,5 pentanedioic acid
4) 1,2,4 tributyl benzene
7) 1,2-dichlorocyclohexane
9) 3-iodo-1-propanal
2) 1 heptanal
5) 3,5 dimethyl- 4 propyl octane
3) 3-hexanone
6) Butyl methyl ether
8) Dicyclopentylmethanone
10) 4,5,6,7-tetrabromo -3,8 dichloro -5,6-diethyl-3,8-dimethyl-1,10-decanedioic acid
35
36
More Organic Compounds
Continued (again)!
Esters:
Organic compounds
O

R - C - OH
(Acid)
O

 R - C - O - R’
(Ester)
Naming:
 Parent Chain
o
o
o
o
 Branches
o
o
Example:
O

C - C - O - C - C-C
2 1
1 2 3
(Parent)
(Alkyl branch)
Parent Chain:
Branch:
Final Name:_______________________________________
37
Example:
O

C - C - C - C - O - C - C
4 3 2 1
1 2
Parent Name:
Branch:
Final Name: __________________________________
Draw: Pentyl Hexanoate
38
Amines:
Organic compounds based on NH3
R - N - R”

R’
Naming:


Primary amine:
(______ hydrogen is replaced by an alkyl group)
C–N–H

H
Name: ___________________________
Secondary amine:
(____ hydrogens are replaced by alkyl groups)
C–N–C - C

H
Name: _____ ______ _______________
Tertiary amine:
(____ hydrogens are replaced by alkyl groups)
C–N–C - C

C–C-C
39
Name: __________________________________________________
Ester and Amine Worksheet
Draw each of the following compounds:
1) ethyl butanoate
2) propyl-benzoate
3) propylamine
4) diethylamine
5) butylethylpropylamine
6) hexyloctylamine
7) methyl-2-methylhexanoate
8) propyl pentanoate
9) phenyl butanoate
40
41
Organic Compounds
Family
Functional Group
Ending
Naming
Alkane
Alkene
Alkyne
Aromatic
Alkyl halides
Alcohol
42
Family
Functional Group
Ending
Naming
Ether
Aldehyde
Ketone
Carboxylic Acid
Ester
Amine
43
Name: __________________________________________________
Mixed Worksheet
Draw each of the following structures:
1) 1-chloro-2-pentyl-4-propyl benzene
3) 2-iodo-3-methyl butanedial
5) propyl undecyl ether
7) 2,5-dimethyl-1-cyclopentanone
9) 1,4,9,11-dodecanetetrol
2) 5-fluoro-2-octyne
4) 5,5-dibromo-1,1,1-trifluoro-8-ethyldecane
6) 1,3,6-heptatriene
8) 2,3,4,5,6-pentafluoro-1-nonanal
10) 4-bromo-5-butyl-3-ethyl-1-cycloheptyne
44
45
Name ___________________________________________________________
Review for Organic Test
Part 1: Draw the following structures:
1. 1,4,7-octanetriol
2. 2,4-dibromo-3-fluoro-1-hexene
3. heptyl hexyl ether
4. butyl pentanoate
5. 3-chloro-5-ethyl heptanal
6. dodecane
7. 4-bromo-5,5-difluoro-3-decanone
8. butyl ethyl pentyl amine
9. 2,3-dimethyl 4-nonene
10. 1-bromo-4-butyl-2-ethyl-3 propyl benzene
11. 1,4,5,trichloro-2-pentyne
12. 2,3,5,7,9 pentabromo-1,4,8-trichloro-6,6 diiodo undecane
46
Part 2: Name the following structures
47
48
Part 3:Model Review
Draw and name each of the models:
#1
#2
Name
Name
#3
#4
Name
Name
#5
#6
Name
Name
49
#7
Name
#8
Name
#9
#10
Name
Name
#11
#12
Name
Name
50
Honors Chemistry Lab Practical
"Organic Chemistry"
Alcohols and Ethers
(3 points, ½ point each)
Grade/Initials
_______________ 1. 2-propanol (rubbing alcohol)
_______________ 2. Butyl ethyl ether
_______________ 3. 3-ethyl-4-methylpentanol
______________ 4. Dicyclopentyl ether
_______________ 5.
Iodo phenyl ether
_______________ 6. 1-fluoro-2-methyl-1,1,2,3-propanetetrol
____________/3___ Total points for Alcohols and Ethers
_____________________________________________________________________________________________________
Aldehydes and Ketones
Grade/Initials (3 points; ½ each)
_______________ 1. propanone (acetone)
_______________ 2. 2-methylpropanal
_______________ 3. 2,2-dimethylpentanal
_______________ 4. methanal (formaldehyde)
_______________ 5. 2-pentanone
_______________ 6. 5-chloro-6,6-dimethyl-3,4-heptadione
_________/3______ Total points for Aldehydes and Ketones
____________________________________________________________________________________________________
Grade/Initials (3 points; ½ each)
Carboxylic Acids
_______________ 1. butanoic acid
_______________ 2. 3-methylpentanoic acid
_______________ 3. 3, 3-difloro-4-ethylhexanoic acid
_______________ 4. 2-butylpropanedioic acid
_______________ 5. 4-ethyl-2-methylheptanoic acid
_______________ 6. benzoic acid (hint, you need to add a carbon off of the ring for the carboxyl group)
_________/3____ Total points for Carboxylic Acids
\
51
Grade/Initials
(3 points; ½ each)
Esters and Amines
_______________ 1. butylamine
_______________ 2. ethylpropylamine
_______________ 3. dimethyl pentylamine
_______________ 4. ethylmethanoate
Design one of the following for 2 points, if right it is placed on the board and other teams may not use it:
_______________ 5. design an ester
name _____________________________________
with 5 carbons total
(can not be straight chain)(Instructor checks)
_______________ 6. design an ester
name _____________________________________
with 7 carbons total
(can not be straight chain)(Instructor checks)
________/3_______ Total points for Esters/Amines
_____________________________________________________________________________________________________
ALL Mixed Up
Grade/Initials
_______________ 1. 4-methyl-2,3-octanediol
_______________ 2. 3-chloro-3-ethyl-2,2,4-trimethylpentane
_______________ 3. 3-propylhexanoic acid
______________ 4. Butyl methyl propyl amine
_______________ 5.
Pentyl propyl ether
_______________ 6.
1-bromo-4-iodo-2-propylbenzene
_______________ 7.
6,6-difluoro-3-methyl-3-propyl-1,4-hexadiyn
_______________ 8.
3-methyl-2,2-difluorobutanal
_______________ 9.
4-ethyl-6-iodo-3,3-dimethyl-1-cyclohexene
_______________ 10. Propylbenzoate
_______________ 11. 5-fluoro-2-methyl-3-hexanone
_______________ 12. 1-fluoro-2-methyl-3-hexanone
Total Points =
/6
52