Organic Chemistry Practice Problems
Organic Chemistry I Practice Set #11 (Chapters 8-10 – Carey)
OH
1) For the following compound, provide a name. Be sure to
identify stereoisomers properly.
C
C
CH3
CH3
2) Fill in what is missing. Either give all of the missing
reagents to complete the reaction or give a structural
H
formula for the major organic product(s). Show
stereoisomers properly if necessary. If no reaction occurs, write N.R. If the product is a racemic
mixture, show both structures.
2g)
2a)
H
CH3
CH3
H
OH
O
CH3
OS
2h) CH3
CH3CH2
CH2CH3
2b)
Br
2c)
O
H
OH
CH3
CH3
H
H
OH
CH2CH3
CH2CH3
CH2CH3
2i)
CH3C≡CCH3
2j)
CH3CH2C≡CCH2CH3
CH3C≡CCH3
2d)
2k)
Br
CH 3
H3 C
CH3CH2C≡CH
2l)
CH3C≡CCH3
2e)
CH2Br
2m)
CH3C≡CCH3
2n)
2f)
CH2Br
This resource was prepared by the Tallahassee Community College Learning Commons
Adapted from practice handouts created by Dr. EF Hilinski of Florida State University
O
Organic Chemistry Practice Problems
3) Provide an efficient multistep synthesis for each of the following conversions of the given starting
material into product. For each transformation, give all necessary reagents and catalysts and give a
structural formula of the organic product. Show stereochemistry appropriately when necessary.
CH2CH3
a) CH3CH2C≡CH 
H
Cl
H
Cl
CH2CH3
b) CH3CH2CH2CHBr2 
Br
c)
Br

4) Using arrows to show the flow of electrons, write a stepwise mechanism for the reaction shown below.
For your mechanism, concisely explain why X = 81% yield and Y = 19% yield when the reaction is
performed at -80°C and why X = 44% yield and Y = 56% yield when the reaction is performed at room
temperature (25°C).
Br
H2C=CHCH=CH2 + HBr 
+
Br
X
Y
This resource was prepared by the Tallahassee Community College Learning Commons
Adapted from practice handouts created by Dr. EF Hilinski of Florida State University
Organic Chemistry Practice Problems
Organic Chemistry I Answers to Practice Set #11 (Chapters 8-10 – Carey)
1) (1R,2S)-2-methyl-1-propynylcyclohexanol
O
2a)
2b) PBr3
Cl
S
2c)
2d)
CH3
N3
O
O
O
2e)
N
2f)
pyridine
CH3
2g)
H
Cl
H
Cl
2h) H2SO4, heat
2k) H2O, H2SO4, HgSO4
2i) Na, NH3
2l)
2j)
2m)
Cl
O
2n)
Br
OH
Cl
Cl
O
H
CH3
Br
HO
H
3a) CH3CH2C≡CH
CH3
H
CH3CH2C≡CCH2CH3
CH2CH3
H
D
H
D
CH2CH3
3b) CH3CH2CH2CHBr2
H
CH3CH2C≡CCH2CH=CH2
H
3c)
Br
Br
CH3CH2C≡CCH2CH=CH2
This resource was prepared by the Tallahassee Community College Learning Commons
Adapted from practice handouts created by Dr. EF Hilinski of Florida State University