~1~ Topic 11: Organic Chemistry Regents Chemistry Mr. Mancuso Properties of Organic Compounds All organic compounds contain ________________________ & __________________________ These compounds are usually associated with _________________________________________ ______________________________________________________________________________ ______________________________________________________________________________ ______________________________________________________________________________ React ______________________ than inorganic compounds (like salts) Often require ____________________ activation energies Have ___________ melting points
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Topic 11: Organic Chemistry
Regents Chemistry Mr. Mancuso
Properties of Organic Compounds
All organic compounds contain ________________________ & __________________________
These compounds are usually associated with _________________________________________
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
React ______________________ than inorganic compounds (like salts)
Often require ____________________ activation energies
Have ___________ melting points
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Organic Prefixes (Reference Table P)
All organic compounds’ names are based on their ______________________________________
# of Carbons
Prefix Alkane Alkane Formula (CnH2n+2)
Alkane Structural Formula
1
2
3
4
5
6
7
8
9
10
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Homologous Series of Hydrocarbons (Reference Table Q)
The Basics:
(a) Carbon will form __________________ bonds
o If all these bonds are single bond, the carbon will be the central atom in a ___________
(b) If an organic compound contains all single bonds, then it is said to be __________________.
CH4
C2H6
(c) If an organic compound contains at least one double or triple bond, then it is said to be
____________________________________________.
C2H4 C2H2
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(d) As the mass of an organic compound increases, so does its ____________________________ and _________________________________________________ because ________________ _____________________________________________________________________________
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Specific Series:
(1) Alkanes
o _____________________________________________________________________
o _____________________________________________________________________
o _____________________________________________________________________
o Examples:
(2) Alkenes
o _____________________________________________________________________
o _____________________________________________________________________
o _____________________________________________________________________
o Examples:
(3) Alkynes
o _____________________________________________________________________
o _____________________________________________________________________
o _____________________________________________________________________
o Examples:
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Naming & Drawing Organic Compounds
(1) The ______________________________________________________________ is the “Parent chain”. This is the “major” compound name.
(2) The carbon atoms of the parent chain are _____________________________________ to establish position of any “deviations” along the chain.
o __________________________________________________________________ __________________________________________________________________ __________________________________________________________________
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(3) “Side” carbon chains are called ______________________________________________
Examples: Locations of these groups are identified with a number before the group name. Isomers:_________________________________________________________________ __________________________________________________________________
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(4) If a particular Alkyl group appears more than once, then ________________________________________________________________________
(5) Different alkyl groups must be listed in ________________________________________
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(6) If the compound is an alkene (parent chain has ________________________________) or an alkyne (parent chain has ______________________________________________)
then a number ___________________________________________________________
(7) If more than one double or triple bond is present in the parent chain, then ________________________________________________________________________
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(8) Halides ________________________________________________________________________ ________________________________________________________________________
Room for More Examples
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Organic Formulas
Organic formulas can be written 2 ways:
__________________________________ ________________________________
Both ways represent the same compound, but the “Expanded” way gives more information about the compound
Example: C6H14
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Example Structure Molecular Formula
“Compressed”
Ethane
Propane
Butane
2-Butene
2-Butyne
1,2-dibromopropane
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Guided Practice Naming and Writing the formulas of Hydrocarbons
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2‐hexyne
2 ‐ butene
2 – methyl ‐ 1 ‐ butene
3 ‐ hexene
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3 – ethyl – 2 – heptene
propyne
1 – butyne
2 ‐ pentyne
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Student Practice Homework #1: Name / Draw Homework #2: Write the condensed and molecular formulas
~17~
1‐pentene
ethane
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ethyne
butane
1‐butyne
ethene
1 – hexyne
2 – methyl butane
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3 – ethyl hexane
1 – pentene
3 – methyl ‐ 1 – butene
3 – methyl ‐ octene
2, 2 – dimethyl butane
3, 3 – dimethyl pentane
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Functional Groups (Reference Table R)
(1) Halides
(2) Alcohols
o Organic compounds with ________________________________________________
o Parent name ends in ‐____________
o Alcohols can be classified by how many hydroxyl groups are attached to the chain
___________________________________________________________
___________________________________________________________
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o Alcohols can also be classified by the number of carbon atoms that are attached to the
carbon holding the hydroxyl group.
Primary, secondary, tertiary classifications
Special case: Glycerol
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(3) Ethers
o Organic compounds in which ________________________________________________________________________
o Name ends in ____________________________________________________________
(4) Aldehydes
o Organic compound in which an ________________________________________________________________________
o Parent name ends in ‐_________________
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(5) Ketones
o Organic compound in which ________________________________________________________________________ ________________________________________________________________________
o Parent chain end in ‐__________________
(6) Organic acids
o Organic compound in which ________________________________________________________________________ ________________________________________________________________________
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(7) Esters
o Parent chain ends in ‐___________________________
(8) Amines
o Parent chain end in ‐________________________________
o Nitrogen can only hold ________________________________
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(9) Amides
o Ends in ‐_______________________________________
o Nitrogen and ____________________________________________________________
(10) Cyclohydrocarbons / “Rings”
o _______________________________________________________________________
o _______________________________________________________________________
o Resonance structures
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Student Practice Homework #1: Name / Draw Write the condensed and molecular formulas
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CH3CH2CH2CH3
CH4
CH3CH2CHO
CH3CH2COOH
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CH3CH2COCH2CH3
CH3OH
CH3OCH2CH2CH3
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Homework #2: Name / Draw Write the condensed and molecular formulas
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~31~
Name each of the following compounds:
CH3COOCH3
CH3OCH3
CH3COCH3
CH3CH2CH2CHO
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Write the condensed formulas for each:
Ethyl propyl ether
butanamide
methyl heptanoate
heptonic acid
~33~
4 – methyl 2,4 ‐ hexdianol
1 ‐ propanamide
trimethyl amine
1 ‐ pentanal
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2,2 – dimethyl pentane
Ethyl pentanoate
2 ‐ butanol
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Organic Reactions
(A) Organic Addition
o ________________________________________________________________________
o ________________________________________________________________________
(B) Substitution
o ________________________________________________________________________
o ________________________________________________________________________
o ________________________________________________________________________
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(C) Combustion
o ________________________________________________________________________
o ________________________________________________________________________
o ________________________________________________________________________
o ________________________________________________________________________
(D) Esterification
o ________________________________________________________________________ ________________________________________________________________________
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(E) Saponification
o ________________________________________________________________________ ________________________________________________________________________
(F) Fermentation
o ________________________________________________________________________ ________________________________________________________________________
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(G) Polymerization
o ________________________________________________________________________ ________________________________________________________________________
o ________________________________________________________________________
o Examples:______________________________________________________________ Addition Polymerization
___________________________________________________________
Condensation Polymerization
___________________________________________________________
___________________________________________________________
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1. Which type of reaction do ethane molecules and ethene molecules undergo when they react with chlorine? (1) Ethane and ethene both react by addition (2) Ethane and ethene both react by substitution (3) Ethane reacts by substitution and ethene reacts by addition (4) Ethane reacts by addition and ethene reacts by substitution
2. Which substance is made up of monomers joined together in long chains? (1) Ketone (2) protein (3) ester (4) acid
3. Which equation represents a substitution reaction?
(1) CH4 + 2 O2 CO2 + 2 H2O
(2) C2H4 + Br2 C2H4Br2
(3) C3H6 + H2 C3H8
(4) C4H10 + Cl2 C4H9Cl + HCl
4. When C3H8 burns completely in an excess of oxygen, the products formed are (1) CO and H2O (2) CO2 and H2O (3) CO and H2 (4) CO2 and H2
5. What are the products of a fermentation reaction? (1) An ester and water (2) A salt and water (3) An alcohol and carbon dioxide (4) A soap and glycerol
6. Which hydrocarbon will undergo a substitution reaction with chlorine? (1) Methane (2) Ethyne (3) Propene (4) Butane
7. The equation CH3OH + CH3OH CH3OCH3 + H2O illustrates the (1) Oxidation of alcohols to form a ketone (2) Oxidation of alcohols to form an acid (3) Dehydration of alcohols to form a polymer (4) Dehydration of alcohols to form an ether
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8. Which process usually produces water as one of the products? (1) Cracking (2) Hydrolysis (3) Addition polymerization (4) Condensation polymerization
9. Esterification is the reaction of an acid with a(n) (1) Water (2) alcohol (3) base (4) salt
For each substance in questions 10‐14, write the number of the organic reaction, chosen from the list below, that will produce this substance Organic Reactions
(1) Esterification (2) Saponification (3) Polymerization (4) Fermentation (5) Substitution (6) Halogen addition
10. Ethanol
11. Glycerol
12. Methyl acetate
13. Polyethylene
14. Dichloromethane
15. What kind of bond is most common in organic compounds? (1) Covalent (2) ionic (3) hydrogen (4) metallic
16. What is the maximum number of covalent bonds that a carbon atom can form? (1) 1 (2) 2 (3) 3 (4) 4
17. A molecule of ethane and a molecule of ethane both have the same (1) Empirical formulas (2) Molecular formulas (3) Number of carbon atoms (4) Number of hydrogen atoms
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18. Which compounds are isomers? (1) 1‐propanol and 2‐propanol (2) Methanoic acid and ethanoic acid (3) Methanol and methanol (4) Ethane and ethanol
19. What is the total number of pairs of electrons that one carbon atom shares with the other carbon atom in a molecule of C2H4? (1) 1 (2) 2 (3) 3 (4) 4
20. A student investigated four different substances in the solid phase. The table below is a record of the characteristics (marked with an X) exhibited by each substance. Which substance has characteristics most like those of an organic compound?
(1) A (2) B (3) C (4) D
21. Which structural formula represents a dihydroxy alcohol?
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Review B
1. Which represents the functional group of an organic acid?
(1) ‐ COOH (2) ‐ OR (3) ‐ CHO (4) ‐ NH2 2. Which formula represents a member of the same homologous series as C4H10 ?
(1) C3H4 (2) C3H5 (3) C3H6 (4) C3H8 3. Which is an isomer of
(1) (3)
(2)
(4) 4. One of the products produced by the reaction between CH3COOH and CH3OH is:
(1) HOH (3) HCOOH (2) H2SO4 (4) CH3CH2OH
5. Which molecule contains four carbon atoms?
(1) butane (3) methane (2) ethane (4) propane
6. Which formula may represent an unsaturated hydrocarbon?
(1) C2H6 (3) C4H10 (2) C3H6 (4) C5H12
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7. Which is the correct structural formula for methanol?
(1)
(3)
(2) (4)
8. How many carbon atoms are contained in an ethyl group?
(1) 1 (2) 2 (3) 3 (4) 4 9. What is the correct formula of 1,1 – dibromoethane?
(1) (3)
(2) (4)
10. Which structural formula represents an alcohol?
(1) (3)
(2) (4)
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11. Which compound can have isomers? (1) C2H4 (3) C2H6 (2) C2H2 (4) C4H8
12. In the alkane series, the formula of each member of the series differs from its preceding
member by: (1) CH (2) CH2 (3) CH3 (4) CH4
13. A solution of methanol differs from a solution of acetic acid in that the solution of acetic acid:
(1) contains molecules only (3) turns red litmus to blue (2) has a pH of 7 (4) conducts electricity
14. What is an isomer of the compound propanoic acid, CH3CH2COOH?
(1) CH2CHCOOH (3) CH3CHOHCH2OH (2) CH3CH2CH2COOH (4) HCOOCH2CH3
15. Which molecular formula represents pentene?
(1) C4H8 (2) C4H10 (3) C5H10 (4) C5H12 16. Which is an isomer of 2,2 – dimethylpropane?
(1) ethane (2) propane (3) pentane (4) butane 17. Which formula represents a dihydroxy alcohol?
(1) C2H4(OH)2 (3) Ba(OH)2 (2) C3H5(OH)3 (4) Al(OH)3
18. Which formula represents an organic acid?
(1) CH3COOH (3) CH3OH (2) CH3OCH3 (4) CH3COOCH3
~45~
19. Which formula represents an aldehyde?
(1) (3)
(2) (4)
20. The name of the compound having the formula C3H5(OH)3 is:
(1) glycerol (3) propene (2) ethylene (4) propanoic acid
21. Molecules of 1 – propanol and 2 – propanol have different:
(1) percentage compositions (3) molecular formulas (2) molecular masses (4) structural formulas
22. Which formula represents a saturated hydrocarbon?
(1) C2H2 (2) C2H4 (3) C3H6 (4) C3H8
23. Which compound is an isomer of CH3COOCH3 ?
(1) CH3OCH3 (3) CH3COOCH3 (2) CH3CH2COOH (4) CH3CH2CH2OH
24. Which compound contains a triple bond?
(1) CH4 (2) C2H2 (3) C3H6 (4) C4H10 25. Organic compounds that are essentially nonpolar and exhibit weak intermolecular forces have:
(1) low melting points (3) high conductivity in solution (2) low vapor pressure (4) high boiling points
26. Each member of the alkane series differs from the preceding member by one additional carbon
atom and: (1) 1 hydrogen atom (3) 3 hydrogen atoms (2) 2 hydrogen atoms (4) 4 hydrogen atoms
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27. All carbon – carbon bonds in a saturated hydrocarbon molecule are:
(1) single covalent (3) triple covalent (2) double covalent (4) coordinate covalent
28. Compared with inorganic compounds, organic compounds usually have:
(1) greater solubility in water (3) more rapid reaction rates (2) a tendency to form ions more readily (4) lower melting points
29. As the molecular mass of the compounds of the alkane series increases, their boiling point:
(1) decreases (2) increases (3) stays the same 30. What is the total number of bonds between adjacent carbon atoms in an ethyne molecule?
(1) 1 (2) 2 (3) 3 (4) 5 31. Which of the following compounds has the lowest normal boiling point?
(1) butane (2) ethane (3) methane (4) propane 32. In an aqueous solution, which compound will be acidic?
(1) CH3COOH (3) C3H5(OH)3 (2) CH3CH2OH (4) CH3OH
33. Compounds which have the same molecular formula but different molecular structures are
called: (1) isomers (3) isotopes (2) allotropes (4) homologs
34. Which is the third member of the alkene series?
(1) propane (2) propene (3) butane (4) butene
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35. Which is an example of a primary alcohol?
(1) (3)
(2) (4) Identify the following organic reactions
36.___________________________
37.___________________________
38.___________________________
39.___________________________
40._______________________________
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