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Organic Practice Set 11 Chapters 8 10

organic chemistry practice question and answers

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26 views4 pages

Organic Practice Set 11 Chapters 8 10

organic chemistry practice question and answers

Uploaded by

Macedih K Eric
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
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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)
CH3 CH3 O
2a)
H OH H OS CH3
2h) CH3
CH2CH3 CH3CH2 O
H OH
2b) CH3 CH3

CH2CH3
Br H H OH 2i)

CH2CH3 CH2CH3 CH3C≡CCH3


2c)
2j)
CH3CH2C≡CCH2CH3
CH3C≡CCH3

2d)
2k) CH 3
Br H3 C
CH3CH2C≡CH
O

2l)

2e) CH3C≡CCH3
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
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 2c) 2d)
Cl S CH3
N3
O O

O
N 2e) 2f)

pyridine

2g) CH3 2h) H2SO4, heat 2k) H2O, H2SO4, HgSO4


H Cl 2i) Na, NH3 2l) 2m) 2n) O
Cl
2j) Br OH
H Cl
Cl Cl
O
H
CH3
Br
HO CH3

H H

3a) CH3CH2C≡CH CH3CH2C≡CCH2CH3

CH2CH3

H D

H D

CH2CH3
H

3b) CH3CH2CH2CHBr2 CH3CH2C≡CCH2CH=CH2


H

3c) Br

CH3CH2C≡CCH2CH=CH2
Br

This resource was prepared by the Tallahassee Community College Learning Commons
Adapted from practice handouts created by Dr. EF Hilinski of Florida State University

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