Organic Chemistry HW 11 PDF

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Summary

Drawing structures, predicting products, completing reactions, mechanisms...

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Chemistry 545 Fall 2017 Homework assignment 11

1. Draw structures for the following compounds. [2 points each] a) 4-bromo-3-heptanone b) (S)-2-methylcyclohexanone c) Z-2-methyl-2-pentenal

d) E-3-hexenal e) p-bromobenzaldehyde f) 3-isopropylheptanal

2. Draw the product of each of the following reactions. [2 points each]

a)

O

O

1. CH3CH2MgBr

d)

CH3CO2H

2. H3O

O b)

c)

+

O

+

CH3NH2

CH3CH2OH excess

O

acid catalyst

e)

Br2

1. CH3MgBr 2. H3O

HCl

3. Fill in the boxes to complete the following reaction sequences. [2 points each]

1. a)

OH

O

O 2.

H3CO OCH3

!

1

1. O

Mg

b)

Br

ether

2. H3O

4. List two different sets of reagents (each set consisting of a carbonyl compound and a Grignard reagent) that could be used to synthesize each of the following secondary alcohols. [4 points each] OH

OH

H3CO

5. Reaction of cyclohexanone with ethylene glycol in the presence of an acid catalyst gives the cyclic acetal shown. Propose a mechanism for this reaction. [8 points] O +

HO

OH

H

O

O

This homework assignment is due at 12:00 noon on Monday December 4, 2017. A late assignment will not be accepted and will be given a grade of zero.

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