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Regents Chemistry: Mr. Palermo

Practice Packet Unit 11:

Organic Chemistry

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LESSON 1: Introduction to Organic Chemistry

1. How many times does carbon bond and why?

2. 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?

a. A B) B C) C D) D

3. How many carbon atoms are in each compound?

a. Methane ____ f. Hexane ____ k. Decane ____

b. Ethane ____ g. Ethyne ____ l. Buyne ____
c. Ethane ____ h. Propane ____ m. Butane ____
d. Pentane ____ i. Heptane ____ n. Propyne ____
e. Propene ____ j. Octane ____ o. Butane ____

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4. For each compound fill in each blank:

Number of Carbon atoms Series Formula
a. Methane ________ ___________ _______________
b. Butane ________ ___________ _______________
c. Propyne ________ ___________ _______________
d. Pentane ________ ___________ _______________
e. Octane ________ ___________ _______________
f. Heptene ________ ___________ _______________
g. Propene ________ ___________ _______________
h. Butyne ________ ___________ _______________
i. Decane ________ ___________ _______________
j. Nonane ________ ___________ _______________
k. Heptane ________ ___________ _______________
l. Ethyne ________ ___________ _______________
m. Hexyne ________ ___________ _______________
n. Ethane ________ ___________ _______________
o. Propane ________ ___________ _______________
p. Decene ________ ___________ _______________
q. Octyne ________ ___________ _______________

5. Circle all the Unsaturated Hydrocarbons above

6. For each of the following use tables P and Q to determine the name.
a. CH4 ________________ f. C9H18 ________________
b. C10H20 ________________ g. C2H6 ________________
c. C3H4 ________________ h. C4H6 ________________
d. C8H18 ________________ i. C7H16 ________________
e. C5H12 ________________ j. C6H12 ________________

7. Create a rule to determine an easy way to find the homologous series to which a compound belongs.

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Lesson 2: Structural Formulas

For each box write the name, molecular and structural formula of the compound

1 Methane CH

X X
4

2 Ethane C H Ethene C H Ethyne C H

2 6 2 4 2 2

4 1-butene C H
4 8

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1. Draw the structural and condensed formula for the following compounds:

a. Butane

b. Pentane

c. Hexane

d. 1-pentyne

e. 2-pentene

f. 3-hexyne

g. 3-hexene

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Lesson 3: Branched Hydrocarbons

Name the following Branched Alkanes

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***

Draw the following Branched alkanes:

4-ethyl-octane

2-methyl-nonane

3-ethyl-2,2-dimethyl-hexane

3,3-dimethyl-pentane

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3-ethyl-pentane

3-ethyl-2methyl-heptane

2,2,3-trimethyl-butane

3-ethyl hexane

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Lesson 4: Isomers
1. Record the Structural formula, molecular formula, and condensed formula for the following:
Name Structural Molecular Condensed

2, 3-dimethyl
butane

2, 2-dimethyl
butane

2-heptyne

3-hexene

2-methyl
1-pentene

2. Where any of the above isomers? Explain your answer. _______________________________________

____________________________________________________________________________________

3. Draw an isomer of 2-heptyne below. Give the name of your isomer: ____________________________

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4. Name the following and identify the isomers.

______________________ ______________________ ______________________

5. Which of the hydrocarbons in the table above were saturated?

6. Draw an isomer of hexane

7. Draw as many isomers of octane as you can (hint there are more than 10)

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Regents Practice

1. Which formula represents an unsaturated 6. What is the general formula for the members
hydrocarbon? of the alkane series?
A) C) A) CnH2n C) CnH2n+2
B) CnH2n–2 D) CnH2n–6

7. In which group could the hydrocarbons all

belong to the same alkene series?
B) D) A) C2H2, C2H4, C2H6
B) C2H2, C2H4, C4H8
C) C2H2, C2H6, C3H6
D) C2H4, C3H6, C4H8

2. Which organic compound is a saturated 8. A molecule of butane and a molecule of 2-

hydrocarbon? butene both have the same total number of
A) ethyne C) ethene A) carbon atoms C) hydrogen atoms
B) ethanol D) ethane B) single bonds D) double bonds

3. Which formula represents a hydrocarbon? 9. A double carbon-carbon bond is found in a

A) CH3CH2CH2CHO molecule of
B) CH3CH2CH2CH3 A) pentane C) pentene
C) CH3CH2CH2COOH B) pentyne D) pentanol
D) CH3CH2COOCH3
10. The multiple covalent bond in a molecule of
4. Which structural formula correctly represents 1-butene is a
a hydrocarbon molecule? A) double covalent bond that has 6 shared
A) B) electrons
B) double covalent bond that has 4 shared
electrons
C) D) C) triple covalent bond that has 6 shared
electrons
D) triple covalent bond that has 4 shared
electrons

5. In saturated hydrocarbons, carbon atoms are 11. Given the formula:

bonded to each other by
A) single covalent bonds, only
B) double covalent bonds, only
C) alternating single and double covalent
bonds What is the IUPAC name of this compound?
D) alternating double and triple covalent A) 2-pentene C) 2-pentyne
bonds B) 2-butene D) 2-butyne

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12. Given the structural formula: 19. Two substances have different physical
and chemical properties. Both substances
have molecules that contain two carbon
atoms, one oxygen atom, and six
hydrogen atoms. These two substances
What is the IUPAC name of this compound? must be
A) propane C) propene A) isomers of each other
B) propanone D) propanal B) isotopes of each other
C) the same compound
13. What is the correct formula for butene? D) the same hydrocarbon
A) C4H4 C) C4H6
B) C4H8 D) C4H10 20. The three isomers of pentane have different
A) formula masses
14. Which general formula represents the B) molecular formulas
homologous series of hydrocarbons C) empirical formulas
that includes the compound l-heptyne? D) structural formulas
A) CnH2n-6 C) CnH2n-2
B) CnH2n D) CnH2n+2 21. Which structural formula represents a
molecule that is not an isomer of pentane?
15. Which compound is an unsaturated A)
hydrocarbon?
A) hexanal C) hexane
B) hexanoic acid D) hexyne

16. Given the structural formula: B)

What is the total number of electrons
shared in the bond between the two
carbon atoms?
A) 6 B) 2 C) 3 D) 4

17. Which formula represents propyne?

A) C3H4 C) C3H6
B) C5H8 D) C5H10

18. What is the name of a compound that has the 22. Which compound is an isomer of pentane?
molecular formula C6H6? A) butane C) propane
A) butane B) butene B) methyl butane D) methyl propane
B) benzene D) butyne
23. What is the maximum number of covalent
bonds that can be formed by one carbon
atom?
A) 1 B) 2 C) 3 D) 4

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24. Which structural formula correctly 27. Organic compounds that are essentially non-
represents an organic compound? polar and exhibit weak intermolecular forces
have
A) low vapor pressure
B) low melting points
C) high boiling points
D) high electrical conductivity in solution

28. A characteristic of most organic compounds

is that they
A) have low melting points
B) have high melting points
25. Atoms of which element can bond with each C) are soluble in water
other to form ring and chain structures in D) conduct electricity when dissolved in
compounds? water
A) C B) Ca C) H D) Na
29. In general, which property do organic
compounds share?
26. Which element must be present in an organic A) high melting point
compound? B) high electrical conductivity
A) hydrogen C) oxygen C) readily soluble in water
B) carbon D) nitrogen D) slow reaction

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Lesson 5: Functional Groups

For each of the following identify the functional group and then name the compound using table R.

Functional Group: _____________ Functional Group: _____________ Functional Group: _____________

Name : ______________________ Name : ______________________ Name : ______________________

Functional Group: _____________ Functional Group: _____________ Functional Group: _____________

Name : ______________________ Name : ______________________ Name : ______________________

Functional Group: _____________ Functional Group: _____________ Functional Group: _____________

Name : ______________________ Name : ______________________ Name : ______________________

Functional Group: _____________ Functional Group: _____________ Functional Group: _____________

Name : ______________________ Name : ______________________ Name : ______________________

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For the following compounds, determine the family and draw the compound:

Name Family Structural Formula Condensed Formula

Butanoic acid

Methanal

Butanamide

3-iodo octane

Methyl pentanonate

Ethanol

2-heptanone

Diethyl ether

2-pentanol

Ethanoic acid

2-propanamine

Hexanal

Ethyl methanoate

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Lesson 6: Organic Reactions

Match the reaction to its name:

___ 1. Addition a. C13H28  C8H18 + C2H4 + C3H6

___ 2. Substitution b. C3H8 + 5O2  3CO2 + 4H20
___ 3. Combustion c. (C17H35COO)3C3H5 + 3 NaOH  C3H5(OH)3 + 3C17H35COONa
___ 4. Cracking d. C6H12O6 C2H5OH +CO2
___ 5. Polymerization e. n(CH2CH2)  (CH2CH2)n
___ 6. Fermentation f. C2H6 + Cl2  C2H5Cl + HCl
___ 7. Esterification g. C3H6COOH + C2H5OH  C3H6COOC2H5 + H2O
___ 8. Saponification h. C3H6 + I2  C3H6I2

Name the reaction:

1. A saturated alkane reacts with fluorine _____________________________

2. Small alkene chains connect to form larger alkane chains _____________________________
3. Sugar is decomposed to form an alcohol _____________________________
4. Large hydrocarbons are heated and break into smaller fragments _____________________________
5. An unsaturated hydrocarbon reacts with bromine _____________________________
6. An alcohol and an organic acid are reacted _____________________________
7. A base is added to a fat molecule to form a soap _____________________________
8. Hydrocarbons are burned in the presence of oxygen _____________________________

Draw all organic reactants and products. Then name and give the formula for the missing substance in the
reaction. Give the reaction type.

9. C2H4 + F2  ________________ Rxn: __________________________

10. C3H6 + H2  ________________ Rxn: __________________________

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11. C2H6 + Cl2  ________________ + HCl Rxn: __________________________

12. C4H10 + Br2  ________________ + HBr Rxn: __________________________

13. CH4 + O2  ______ + H2O Rxn: __________________________

14. C3H8 + O2  CO2 + ______ Rxn: __________________________

15. C6H12O6  2O2 + 2________________ Rxn: __________________________

16. C8H18  C6H12 + ________________ Rxn: __________________________

17. C2H5OH + C3H7COOH  H2O + ________________ Rxn: __________________________

18. C5H10 + F2  ________________ Rxn: __________________________

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Review:

1. Base your answer to the following question on the information below.

The incomplete equation below represents an esterification reaction. The

alcohol reactant is represented by X.

Draw the structural formula for the alcohol represented by X.

2. A gasoline engine burns gasoline in the presence of excess oxygen to form carbon dioxide and
water. The main components of gasoline are isomers of octane. A structural formula of octane is
shown below.

Draw a structural formula for 2,2,4-trimethylpentane.

Base your answers to questions 3 and 4 on the information below.

Many esters have distinctive odors, which lead to their widespread use as
artificial flavorings and fragrances. For example, methyl butanoate has an odor like
pineapple and ethyl methanoate has an odor like raspberry.

3. What is a chemical name for the alcohol that reacts with methanoic acid to produce
the ester that has an odor like raspberry?

4. Draw a structural formula for the ester that has an odor like pineapple.

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Base your answers to questions 5 through 7 on the equation below, which

represents an organic compound reacting with bromine.

5. What is the gram-formula mass of the product in this reaction?

6. What type of organic reaction is represented by this equation?

7. What is the IUPAC name for the organic compound that reacts with Br2?

Base your answers to questions 8 through 11 on the information and diagram below and on your
knowledge of chemistry.

Crude oil is a mixture of many hydrocarbons that have different numbers of carbon
atoms. The use of a fractionating tower allows the separation of this mixture based on
the boiling points of the hydrocarbons. To begin the separation process, the crude oil is
heated to about 400°C in a furnace, causing many of the hydrocarbons of the crude oil
to vaporize. The vaporized mixture is pumped into a fractionating tower that is usually
more than 30 meters tall. The temperature of the tower is highest at the bottom. As
vaporized samples of hydrocarbons travel up the tower, they cool and condense. The
liquid hydrocarbons are collected on trays and removed from the tower. The diagram
below illustrates the fractional distillation of the crude oil and the temperature ranges
in which the different hydrocarbons condense.

8. How many hydrogen atoms are present in one molecule of octane?

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9. Write an IUPAC name of one saturated hydrocarbon that leaves the fractionating tower at less than
40°C.

10. Describe the relationship between the strength of the intermolecular forces and
the number of carbon atoms in the different hydrocarbon molecules.

11. State the trend between the boiling point of the hydrocarbons contained in the crude
oil and the number of carbon atoms in these molecules.

Base your answers to questions 12 and 13 on the information below. Given the reaction between
1-butene and chlorine gas:
C4H8 + Cl2  C4H8Cl2

12. Draw the structural formula of the product 1,2-dichlorobutane

13. Which type of chemical reaction is represented by this equation?

Base your answers to questions 14 and 15 on the information below.

Diethyl ether is widely used as a solvent.

14. Draw the structural formula for an alcohol that is an isomer of diethyl ether.

15. In the space provided draw the structural formula for diethyl ether.

16. How is the bonding between carbon atoms different in unsaturated hydrocarbons and
saturated hydrocarbons?

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