Unit 13 Question Packet
Organic Chemistry
S KILLS
1. Identifying P ROPERTIES OF
2. Naming & Drawing H
O RGANIC C
YDROCARBONS
OMPOUNDS
Name ………………………………………………
Period ………….
4.
Identifying F UNCTIONAL G ROUPS (T ABLE R)
5. Identifying O RGANIC R EACTIONS
3. Identifying & Drawing I SOMERS
S KILL #1: Identifying P ROPERTIES OF O RGANIC C OMPOUNDS refer to your notes & RB p. 149
1.
Which type of bonds and solids are characteric of organic compounds?
(1) ionic bonds and ionic solids
(2) ionic bonds and molecular solids
(3) covalent bonds and ionic solids
(4) covalent bonds and molecular solids
2.
In general, which property do organic compounds share?
(1) high melting points
(2) high electrical conductivity
(3) high solubility in water
(4) slow reaction rate
3.
A carbon atom in any organic compound can form a total of
(1) 1 covalent bond
(2) 2 covalent bonds
(3) 3 covalent bonds
(4) 4 covalent bonds
S KILL #2:
4.
Which best explains why there are more organic compounds than inorganic compounds?
(1) the carbon atom readily forms covalent bonds with other carbon atoms
(2) the carbon atom readily forms ionic bonds with other carbon atoms
5.
Atoms of which element can bond to each other to form chains, rings, and networks?
(1) carbon (3) hydrogen
6.
(3) the carbon atom readily combines with oxygen
(4) the carbon atom readily dissolves in water
(2) fluorine compound?
(4) oxygen
Which element must be present in an organic
(1) hydrogen (3) carbon
(2) oxygen (4) nitrogen
Naming & Drawing H YDROCARBONS refer to your notes, RB p. 150-152, & Tables P & Q
Hydrocarbons are classified into three Homologous Series – groups of hydrocarbon compounds that differ by the number of CH
2
units they have.
 Use TABLES P and Q to answer the following questions.
7. In terms of bond type, how are alkanes, alkenes, and alkynes different from one another?
Alkanes have single bonds , alkenes have double bonds , and alkynes have triple bonds.
8. Alkanes are called saturated hydrocarbons. Alkenes and alkynes are called unsaturated hydrocarbons. What determines if a hydrocarbon is “saturated” or “unsaturated”?
All single bonds = “saturated” (alkanes)
Double or triple C to C bonds means the hydrocarbon is “unsaturated” (alkenes & alkynes)
9. Below are the STRUCTURAL FORMULAS of three different hydrocarbons. Complete the table.
Structural formula
Molecular formula
Name
Saturated or
Unsaturated?
C
4 butyne
H
6 unsaturated
C
4
H
10 butane saturated
C
3
H
6 propyne unsaturated

10. Fill in the table below.
Molecular
C
Formula
2
H
6 ethane
C
C
3
4
H
H
6
6 propene butyne
C
3
H
4
C
7
H
14
C
5
H
12 propyne heptene pentane
Name
C
C
C
C
C
5
9
C
3
6
4
8
CH
H
H
C
10
H
H
H
4
10
20
H
H
8
6
12
18
18 pentene nonane decyne propane hexene butyne octane methane
C
7
H
14 heptene
11. Which compound is a saturated hydrocarbon?
(1) propanal (3) propene
(2) propane (4) propyne
12. Which compound is a member of the same homologous series as C
3
H
8
?
(1) CH
(2) C
4
4
H
8
(3) C
(4) C
5
6
H
H
8
10
13. A molecule of a compound contains a total of 10 hydrogen atoms and has the general formula C n
H name of this compound?
(1) but-
2n+2
. Which prefix is used in the
(3) oct-
(2) dec- (4) pent-
14. Which compound is a saturated hydrocarbon?
(1) CH
2
CH
2
(3) CH
3
CHO
(2) CH
3
CH
3
(4) CH
3
CH
2
OH
15. Which formula represents an alkene?
(1) C
(2) C
2
3
H
H
6
6
(3) C
(4) C
4
5
H
H
10
12
16. Which formula represents an unsaturated hydrocarbon?
(1) CH
2
CHCl (3) CH
(2) CH
3
CH
2
Cl (4) CH
3
CH
3
2
CH
CHCH
2
3
17. Identify the homologous series of hydrocarbons to which CH alkenes
3
CHCH
2
belongs.
Homologous Series alkanes alkenes alkynes alkynes alkenes alkanes alkenes alkanes alkynes alkanes alkenes alkynes alkanes alkanes alkenes
Saturated or
Unsaturated? saturated unsaturated unsaturated unsaturated unsaturated saturated unsaturated saturated unsaturated saturated unsaturated unsaturated saturated saturated unsaturated
18. Which formula represents an unsaturated hydrocarbon?
19. Which compound is a saturated hydrocarbon?
(1) hexane
(2) hexene
(3) hexanol
(4) hexanal
20. Given the formula of a substance:
2
What is the total number of shared electrons in a molecule of this substance?
(1) 22 (3) 9
(2) 11
21. Hydrocarbons are compounds that contain
(1) C, only
(2) C and H, only (4) C, H, O, and N, only
22. Which general formula represents the compound CH
(1) C
(2) C n n
H n
H
2n
3
CH
2
(4) 6
(3) C, H, and O, only
CCH?
(3) C n
H
2n–2
(4) C n
H
2n+2

Naming Hydrocarbons using IUPAC Rules (International Union of Pure & Applied Chemistry)
1.
Find the longest chain of carbon atoms and trace around it – this is the “parent chain”
 Use the Organic prefix to tell the # of C atoms in the parent chain ( TABLE P )


Use “ANE” ending if it’s an alkane (all single bonds)
Use “ENE” ending if it’s an alkene (double bond between two carbon atoms)

Use “YNE” ending if it’s an alkyne (triple bond between two carbon atoms)
2.
If it is an alkENE or alkYNE

Number the C atoms in the parent chain to give the multiple bond the lowest possible number
3.
If it is a branched alkane

Number the C atoms in the parent chain to give the branch the lowest possible number

Name the branch: organic prefix w/ “yl” ending (ex: methyl, ethyl, propyl, etc.)
* Number the carbons to give the lowest possible number for the branch/bond locations *
* Dashes “-“ separate numbers and words *
23. Give the correct IUPAC name for the following hydrocarbons AND write their molecular formulas.
(a) (b) (c)
(d)
2 – methylbutane
C
5
H
12
(e)
2 – methylbutane
C
5
H
12
(f)
2 – methylpropane
C
4
H
10
(g)
3 – methylpentane
C
6
H
14 pentane
C
5
H
12
(h) (i)
2 – methylheptane
C
8
H
18
2 – butyne
C
4
H
6
(j) (k)
2 – pentyne
C
5
H
8
2 – hexene
C
6
H
12
24. Identify which of the compounds above are isomers of each other.
(a)/(b) and (e) (h) and (l)
(l) heptane
C
7
H
16
2 – butene
C
4
H
8 butyne
C
4
H
6

S KILL #3: Identifying & Drawing I SOMERS refer to your notes, RB p. 158-159
25. For each of the pairs of compounds below, state whether they are isomers of one another:
Compounds Isomers?
Yes!
Yes!
2-propanone propanal
No
propanal propanoic acid
26. Which two compounds are isomers of each other?
(1) CH
3
CH
2
(2) CH
3
(3) CH
3
CH
2
COOH and CH
CHBrCH
3
COOCH
2
CHO and CH
3
3
and CH
2
COCH
3
BrCHBrCH
3
CH
3
30. Which compound has an isomer?
(4) CH
3
CHOHCH
3
and CH
3
CHOHCH
2
OH
27. The compounds CH
3 must have the same
OCH
3
and CH
3
CH
2
OH are isomers of each other. These two compounds
(1) density
(2) reactivity
(3) melting point
(4) molecular formula
28. Given the structural formulas:
Which two formulas represent compounds that are isomers of each other?
(1) A and B
(2) A and C
(3) B and D
(4) C and D
29. Given the formulas for two compounds:
4
31. The isomers butane and methylpropane differ in their
(1) molecular formulas
(2) structural formulas
(3) total number of atoms per molecule
(4) total number of bonds per molecule
32. 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 must be
These compounds differ in
(1) gram-formula mass
(2) molecular formula
(3) percent composition by mass
(4) physical properties at STP
(1) isomers of each other
(2) isotopes of each other
(3) the same compound
(4) the same hydrocarbon
33. Which pair of compounds are isomers?
(1) NO
2
and N
2
O
4
(2) P
2
O
5
and P
4
O
10
(3) HCOOH and CH
(4) CH
3
OCH
3
and C
3
2
COOH
H
5
OH

34. In the boxes below, draw the following hydrocarbons. In the adjacent box, draw an isomer of the hydrocarbon AND NAME IT using IUPAC rules.
* ALWAYS draw the parent chain FIRST
* ALL C’s must have 4 bonds!!!
(a) pentane
MANY POSSIBLE iSOMERS!
Isomer name: 2-methylbutane
(b) 2-pentene Isomer name:
(c) 2-pentyne Isomer name: pentyne
(d) 2-butene Isomer name: butene
(e) 2-butyne Isomer name: butyne
(f) 2-methylpropane Isomer name: butane
(g) 3-ethylheptane Isomer name: nonane

S KILL #4: Identifying F UNCTIONAL G ROUPS (T ABLE R) refer to your notes, RB p. 153-157

(a) In terms of bonding, how are alcohols and organic acids different?
Alcohols – single bond to O Organic acids – double bond to O
(b) In terms of chemical properties, how are all organic acids alike? Conduct electricity, donate H +
(c) In terms of chemical properties, how are organic acids and alcohols different?
Alcohols do NOT conduct electricty or donate H + like acids do
(d) In terms of structure, how are ketones and aldehydes different?
Ketones have a double bond to O in the middle of the molecule, aldehydes have a double bond to O at the end of a molecule
(e) In terms of bonding, how are esters and ethers different?
Esters have a double bond to O and a single bond to O, ethers only have a single bond to O
(f) In terms of bonding, how are ketones and esters different?
Esters have an extra O in their formulas, attached by a single bond

10. Which Lewis electron-dot diagram represents chloroethene?
14. Given the structural formula:
11. Given the formula:
1
What is the IUPAC name of this compound?
(1) pentanal
(2) pentanol
(3) methyl pentanoate
(4) pentanoic acid
15. What is the IUPAC name for the compound that has the condensed structural formula
CH
3
CH
2
CH
2
CHO?
(1) butanal
(2) butanol
(3) propanal
(4) propanol
16. What is the total number of pairs of electrons shared between the carbon atom and the oxygen atom in a molecule of methanal?
(1) 1 (3) 3
(2) 2 (4) 4
17. Given the structural formula:
This compound is classified as
(1) an aldehyde
(2) an amide
(3) an amine
(4) a ketone
12. What is the total number of carbon atoms in a molecule of ethanoic acid?
(1) 1
(2) 2
(3) 3
(4) 4
13. Which of these compounds has chemical properties most similar to the chemical properties of ethanoic acid?
(1) C
3
H
7
(2) C
2
H
5
COOH (3) C
2
H
5
OH (4) C
2
H
5
COOC
2
OC
2
H
5
H
5
This structural formula represents a molecule of
(1) an aldehyde (3) a ketone
(2) an ester (4) an amino acid
18. A thiol is very similar to an alcohol, but a thiol has a sulfur atom instead of an oxygen atom in the functional group. One of the compounds in a skunk’s spray is 2-butene-1-thiol. The formula of this compound is shown below.
(a) Explain, in terms of composition, why this compound is a thiol.
There is a sulfur atom instead of an oxygen atom in the functional group.
(b) Explain, in terms of electron configuration, why oxygen atoms and sulfur atoms form compounds with similar molecular structures.
Oxygen and sulfur atoms have the same number (six) of valence electrons. OR
Atoms of both elements need two more valence electrons to complete their outer shells.
(c) A small amount of methanethiol, which has a distinct odor, is added to propane to help consumers detect a propane leak. In methanethiol, the odor is caused by the thiol functional group (–SH).
Methanethiol, CH
3
SH, has a structure that is very similar to the structure of methanol.
Draw a structural formula for a molecule of methanethiol.
Ans:

S KILL #5: Identifying O RGANIC R EACTIONS
19. The reaction that joins thousands of small, identical molecules to form one very long molecule is called
(1) esterification (3) polymerization
(2) fermentation (4) substitution
20. Given the balanced equation for an organic reaction:
C
2
H
2
+ 2Cl
2
 C
2
H
2
Cl
4
This reaction is best classified as
(1) addition (3) fermentation
(2) esterification (4) substitution
21. Given the incomplete equation for the combustion of ethane:
2C
2
H
6
+ 7O
2
 4CO
2
+ 6 ____
What is the formula of the missing product?
(1) CH
3
OH
(2) HCOOH
(3) H
2
(4) H
2
O
O
2
22. Given the balanced equation representing a reaction:
CH
3
CH
2
CH
3
+ Br
2
 CH
3
CH
2
CH
2
Br + HBr
This organic reaction is best classified as
(1) an addition reaction
(2) an esterification reaction
(3) a polymerization reaction
(4) a substitution reaction
23. Given the balanced equation with an unknown compound represented by X:
Which compound is represented by X?
(1) CH
3
OH(aq) (3) CH
3
CH
2
OH(aq)
(2) CH
2
(OH)
4
(aq) (4) CH
2
OHCH
2
OH(aq)
24. Given the incomplete equation representing an organic addition reaction:
Which compound could be represented by X?
(1) CH
(2) C
2
4
H
4
(3) C
3
H
8
(4) C
4
H
10
25. The process of joining many small molecules into larger molecules is called
(1) neutralization
(2) polymerization
(3) saponification
(4) substitution
refer to your notes, RB p. 160-162
26. Given the equation:
X + Cl
2
 C
2
H
5
Cl + HCl
Which molecule is represented by X?
(1) C
2
H
4
(3) C
3
H
6
(2) C
2
H
6
(4) C
3
H
8
27. Which type of reaction is represented by the equation below?
Note: n is a very large number equal to about 2000
(1) esterification
(2) fermentation
(3) saponification
(4) polymerization
28. In which reaction is soap a product?
(1) addition (3) saponification
(2) substitution (4) polymerization
29. Given the equation:
C
2
H
6
+ Cl
2
 C
2
H
5
Cl + HCl
This reaction is best described as
(1) addition involving a saturated hydrocarbon
(2) addition involving an unsaturated hydrocarbon
(3) substitution involving a saturated hydrocarbon
(4) substitution involving an unsaturated hydrocarbon
30. Given the reaction:
This reaction is an example of
(1) fermentation
(2) saponification
(3) hydrogenation
(4) esterification
31. Which formula correctly represents the product of an addition reaction between ethene and chlorine?
(1) CH
2
(2) CH
3
Cl
2
Cl
(3) C
2
H
4
(4) C
2
H
3
Cl
2
Cl

32. Many artificial flavorings are prepared using the type of organic reaction shown below.
(a) What is the name of this organic reaction? _______________________________esterification or making an ester
(b) To what class of organic compounds does reactant 2 belong? _______________alcohol
(c) Draw the structural formula of an isomer of reactant 2.
33. In the space to the right of the reactants and arrow below, draw the structural formula for the product of the reaction shown.
34. Given the equation: butanoic acid + 1-pentanol  water + X
To which class of organic compounds does product X belong? ______________________esters
35. Given the reaction between 1-butene and chlorine gas:
C
4
H
8
+ Cl
2
 C
4
H
8
Cl
2
(a) Which type of chemical reaction is represented by this equation? _________________________
addition, redox, synthesis
(b) Draw the structural formula of the product 1,2-dichlorobutane.
36. Given the balanced equation for an organic reaction between butane and chlorine that takes place at
300.°C and 101.3 kilopascals:
C
4
H
10
+ Cl
2
→ C
4
H
9
Cl + HCl
(a) Identify the type of organic reaction shown. ____________________ substitution
(b) Draw a structural formula for the organic product.

37. 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.
(a) Draw a structural formula for the ester that has an odor like pineapple.
Ans:
(b) What is a chemical name for the alcohol that reacts with methanoic acid to produce the ester that has an odor like raspberry? ethanol
38. The hydrocarbon 2-methylpropane reacts with iodine as represented by the balanced equation below. At standard pressure, the boiling point of 2-methylpropane is lower than the boiling point of 2-iodo-2methylpropane.
(a) To which class of organic compounds does this organic product belong? ______________________ halocarbons OR halides
(b) Explain, in terms of bonding, why the hydrocarbon 2-methylpropane is saturated.
There are only single bonds in methylpropane
(c) Explain the difference in the boiling points of 2-methylpropane and 2-iodo-2-methylpropane in terms of
both molecular polarity and intermolecular forces.
The molecules of 2-iodo-2-methylpropane are more polar and have stronger IMF than the molecules of
2-methylpropane.
39. The equation below represents the reaction between butanoic acid and an unidentified reactant, X.
(a) Identify the type of organic reaction represented by the equation. ________________________ esterification
(b) Write the molecular formula of the organic product in the equation. ___________________ C
6
H
12
(c) Draw a structural formula for the unidentified reactant, X, in the equation.
O
2
(ethanol)

40. During a bread-making process, glucose is converted to ethanol and carbon dioxide, causing the bread dough to rise. Zymase, an enzyme produced by yeast, is a catalyst needed for this reaction.
(a) Balance the equation below for the reaction that causes bread dough to rise, using the smallest wholenumber coefficients.
1,2,2
(b) Draw a structural formula for the alcohol formed in this reaction.
(ethanol)
(c) State the effect of zymase on the activation energy for this reaction.
Zymase lowers the activation energy.
41. Biodiesel is an alternative fuel for vehicles that use petroleum diesel. Biodiesel is produced by reacting vegetable oil with CH
3
OH. Methyl palmitate, C
15
H
31
COOCH
3
, a compound found in biodiesel, is made from soybean oil. One reaction of methyl palmitate with oxygen is represented by the balanced equation below.
(a) Write an IUPAC name for the compound that reacts with vegetable oil to produce biodiesel.
_____________________ methanol
(b) Explain, in terms of both atoms and molecular structure, why there is no isomer of CH
3
There are too few atoms to create a different molecular structure.
OH.
(c) Identify the class of organic compounds to which methyl palmitate belongs. __________________ ester
(d) Identify the type of organic reaction represented by the balanced equation. __________________ combustion
(e) State evidence from the balanced equation that indicates the reaction is exothermic.
Energy is on the right side of the arrow.
42. Base your answers to the following questions on the condensed structural formula below.
CH
3
CH
2
CHCH
2
(a) Draw the structural formula for this compound.
(b) The formula below represents a product formed when HCl reacts with CH
3
CH
2
CHCH
2
.
What is the IUPAC name for this product? ________________________________ 2-chlorobutane
(c) Identify the type of organic reaction described in (b). __________________________addition