Download HONORS ORGANIC CHEM. HAHS MRS. RICHARDS 1 ORGANIC

HONORS ORGANIC CHEM.
HAHS
MRS. RICHARDS
ORGANIC CHEMISTRY: FINAL EXAM REVIEW
List of Topics: While the exam will specifically focus on material from Quarter 2, an understanding of several
important concepts from Quarter 1 is also required.
1.) Naming: alkenes, alkynes, enynes, alcohols
2.) Reactions: alkenes and alkynes: determining products, reagents, reactants
3.) Mechanisms: alkenes and alkynes: electrophilic addition of HX (both), halohydrin formation (alkenes
only), acid-catalyzed hydration (both), hydroboration (both), acetylide anion formation/
alkylation (alkynes only)
While there are no multiple choice or fill-in-the-blank questions on the exam, answering the
following review questions will help assess your understanding of the concepts above and your
ability to apply the information in the open-ended questions on the test.
NAMING REVIEW
1. When naming an alkene or an alkyne, always find the longest chain containing the double or triple bond and
start numbering this way:
2. In a cycloalkene, number the ring so that the double bond is always between ______ and ______ and the
first substituent has as _______ a number as possible.
3. The name of alkenes end in _______ and alkynes end in _______.
4. At the end of the name, include the number indicating where the ___________________________ begins.
5. Enynes contain both an ______________ and an _______________.
6. To name an enyne, find the longest chain containing both functional groups and begin numbering this way:
7. When the double and triple bonds are equidistant from the end point of a carbon chain, always give the
____________ the lowest number.
8. When naming an alcohol, find the longest chain containing the –OH and begin numbering this way:
9. The name of alcohols ends in ______.
10. At the end of the alcohol’s name, include the number indicating where the _________ occurs along the
carbon chain.
11. Name the following molecules (continued on next page).
A
B
C
D
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HONORS ORGANIC CHEM.
11. cont’d
E
HAHS
F
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MRS. RICHARDS
G
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HO
K
OH
OH
H
L
M
OH
OH
OH
HO
REACTIONS REVIEW
12. Alkenes and alkynes both undergo electrophilic addition reactions. In this general type of reaction:
a.) Describe what acts as the nucleophile.
b.) What type of intermediate forms?
c.) Explain how Markovnikov’s Rule applies.
13. When HX adds to an alkyne or alkene, describe how you know which carbon the H adds to and which
carbon the X adds to and why.
14. When X2 adds to an alkene, where do the X’s end up?
15. a.) When 1 eq. X2 adds to an alkyne, where do the X’s end up?
b.) When excess X2 adds to an alkyne, where do the X’s end up and how many total add?
16. When X2/ H2O adds to an alkene, a halohydrin forms in which _____ adds to the more substituted carbon
and _____ adds to the less substituted carbon.
17. Both alkenes and alkynes undergo hydration reactions. What gets added in a hydration reaction?
18. a.) To form the Markovnikov alcohol, add _______________ to an alkene.
b.) To form the anti-Markovnikov alcohol, add _____________ to an alkene.
19. When alkynes undergo hydration reactions, an enol forms first.
a.) What is an enol?
b.) What reagents are used to make the Markovnikov enol?
c.) What reagents are used to make the anti-Markovnikov enol?
d.) What happens after the enol forms and what functional groups do the final products contain?
20. Alkenes undergo hydroxylation reactions to form diols. What reagents are used to form the diol?
21. Both alkenes and alkynes undergo oxidative cleavage reactions.
a.) What are the reagents used in oxidative cleavage?
b.) Describe what happens to the alkene/ alkyne bond in this type of reaction.
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HONORS ORGANIC CHEM.
HAHS
MRS. RICHARDS
c.) How do the products of alkene cleavage differ from those of alkyne cleavage?
d.) How do the products of alkyne cleavage differ when the alkyne is internal vs. terminal?
22. Alkynes are typically formed via this general type of reaction: __________________.
a.) Vinylic halides react with ___________ to form alkynes.
b.) 1,2-dihalides react with ___________ to form alkynes.
23. Alkynes undergo reduction reactions which result in an increase in this type of bond:
a.) Complete reduction occurs when the alkyne reacts with ___________ to form an _____________.
b.) Incomplete reduction occurs when the alkyne reacts with ______________ to form a cis alkene or with
_______________ to form a trans alkene.
24. Terminal alkynes are weakly acidic; they react with _________ to form this type of anion:
25. When an alkylation reaction occurs, the acetylide anion reacts with a _________________ to form a new
_______________ bond.
26. Draw the product of each reaction.
a.)
1. BH3
O3
h.)
2. H2O2/ OH-
Zn, H3O+
Br
b.)
Cl2
NaNH2
i.)
1 eq.
c.)
d.)
Br2
Cl2
HCl
j.)
1. OsO4
k.)
2. NaHSO3
H2O
Li
e.)
f.)
NH3
1. BH3
Cl2
l.)
excess
O3
m.)
2. H2O2/ OH-
Zn, H3O+
Br
H2O
g.)
H2SO4
KOH
n.)
Br
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HONORS ORGANIC CHEM.
HAHS
MRS. RICHARDS
26. cont’d
HCl
o.)
t.)
1 eq.
H2O
p.)
r.)
s.)
u.)
H3O+
HCl
excess
Br2
H2O
HBr
v.)
O3
Zn, H3O+
1. NaNH2
H2
w)
Pd / C
2. CH3CH2Br
H2
x.)
Lindlar
27. Identify the reagents needed to perform each reaction as shown.
O
a.)
H
OH + CO2
h.)
O
Cl
Br
i.)
b.)
Cl
OH
j.)
c.)
Br
Br
Br
Br
OH
OH
d.)
OH
H
e.)
k.)
O
O
Br
l.)
Br
Br
m.)
f.)
Br
O
g.)
n.)
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HONORS ORGANIC CHEM.
HAHS
MRS. RICHARDS
27. cont’d
Br
r.)
o.)
Cl
OH
p.)
Br
Br
s.)
Br
t.)
q.)
MECHANISMS REVIEW
28. When drawing a reaction mechanism, the arrow always begins where the electrons _______ and points to
where the electrons ___________.
29. We have seen two types of reaction mechanisms that do not occur through carbocation intermediates. What
are they? (*We have seen several reactions that do not occur through carbocations; this question is
specifically about reactions for which we have seen mechanisms.)
30. Draw the mechanism for each reaction shown below. Be sure to clearly show arrows as well as any bonds
that break/ form and any + / ─ charges that form.
Br
HBr
A.)
E.)
H
1. BH3
O
2. H2O2/ OH-
B.)
HCl
H2O
H2SO4
F.)
OH
HO
C.)
Br2
H2O
D.)
G.)
2. H2O2/ OH-
H.)
OH
1 eq.
1. NaNH2
2. CH3CH2Br
Br
1. BH3
Cl
H2O
H2SO4
O
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