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Problem Set 7

This document contains 9 problems related to alcohol reactions and mechanisms. Problem 1 asks to name 3 alcohols using IUPAC rules and denote stereochemistry. Problem 2 asks to draw structures of 3 specific alcohols. Problem 3 asks to draw products and mechanisms of an alcohol dehydration and list alternative dehydration reagents. The remaining problems ask to propose mechanisms or draw products for various alcohol reactions, including rearrangements, hydride shifts, substitutions, and eliminations.

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Ryan Leung
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34 views5 pages

Problem Set 7

This document contains 9 problems related to alcohol reactions and mechanisms. Problem 1 asks to name 3 alcohols using IUPAC rules and denote stereochemistry. Problem 2 asks to draw structures of 3 specific alcohols. Problem 3 asks to draw products and mechanisms of an alcohol dehydration and list alternative dehydration reagents. The remaining problems ask to propose mechanisms or draw products for various alcohol reactions, including rearrangements, hydride shifts, substitutions, and eliminations.

Uploaded by

Ryan Leung
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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Problem Set 7

1. Name the following alcohols using IUPAC rules. Remember to denote stereochemistry if appropriate!!

OH
Cl

OH
OH

2. Draw structures of the following alcohols.

(1R,3R)-3-bromocyclopentanol 5-sec-butyl-6-fluoro-2-methyl-1-nonanol cyclobutanol

3. Draw all possible products of the following dehydration reaction. If more than one product can be formed,
label the MAJOR isomer.
In the space below, draw out the complete mechanism to account for formation of the MAJOR product.
Also, what is the alternative set of reagents we can use to dehydrate an alcohol?

alternate reagents?

H2SO4
OH

  1  
4. Reactions that proceed via a carbocation intermediate (SN1 and E1) can give unexpected products. Please
consider the following example:

H2SO4
+
H2O expected,
OH but not
minor major
observed
observed products

How? When you form a carbocation intermediate, they can rearrange to form a more stable carbocation.

Mechanism:

5. Propose a mechanism for formation of the following products:

Br
HBr
Br
OH expected,
but not
observed

  2  
6. The following reaction is a "ring expansion" rearrangement. Please account for both products.

OH H3PO4
+
H2O

7. Provide a mechanism for the following transformation:

H2SO4
H 2O
OH

8. Provide a mechanism for the following hydride shift:

OH
Br
HBr

  3  
9. Draw  the  major  organic  product  in  the  box  for  each  reaction.  

2HBr

Br

POCl3
NaH pyridine
SOCl2

OH
HBr H2SO4

HCl
(CHP10)
O
PBr3

OH
H2O, H+
CHP 10

  4  
O

mechanism?
H-I
NaH

OH

SOCl2
pyridine

PBr3
mechanism(s) for the
above reaction?

KOC(CH3)3
mechanism?

Cl

  5  

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