Melting point is sometimes used as an indication of the extent of ionic bonding in a compound—the higher the melting point, the more ionic the substance. On this basis, oxides of metals seem to become less ionic as the charge on the metal ion increases. Thus, Cr 2 O 3 has a melting point of 2266 °C while CrO 3 has a melting point of only 196 °C . The explanation often given is similar in some respects to explanations of the variations in the strengths of certain intermolecular attractions given in this chapter. Provide an explanation for the greater degree of electron sharing in CrO 3 as compared with Cr 2 O 3 .
Melting point is sometimes used as an indication of the extent of ionic bonding in a compound—the higher the melting point, the more ionic the substance. On this basis, oxides of metals seem to become less ionic as the charge on the metal ion increases. Thus, Cr 2 O 3 has a melting point of 2266 °C while CrO 3 has a melting point of only 196 °C . The explanation often given is similar in some respects to explanations of the variations in the strengths of certain intermolecular attractions given in this chapter. Provide an explanation for the greater degree of electron sharing in CrO 3 as compared with Cr 2 O 3 .
Melting point is sometimes used as an indication of the extent of ionic bonding in a compound—the higher the melting point, the more ionic the substance. On this basis, oxides of metals seem to become less ionic as the charge on the metal ion increases. Thus,
Cr
2
O
3
has a melting point of
2266 °C
while
CrO
3
has a melting point of only
196 °C
. The explanation often given is similar in some respects to explanations of the variations in the strengths of certain intermolecular attractions given in this chapter. Provide an explanation for the greater degree of electron sharing in
CrO
3
as compared with
Cr
2
O
3
.
Kumada Coupling:
1. m-Diisobutylbenzene below could hypothetically be synthesized by Friedel-Crafts reaction. Write out the reaction with a
mechanism and give two reasons why you would NOT get the desired product.
Draw the reaction (NOT a mechanism) for a Kumada coupling to produce the molecule above from m-dichlorobenzene.
Calculate the theoretical yield for the reaction in question 2 using 1.5 g of p-dichlorobenzene and 3.0 mL isobutyl bromide.
What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What
other impurities are present in your product and how do you know?
Wintergreen from Aspirin:
1. In isolating the salicylic acid, why is it important to press out as much of the water as possible?
2. Write the mechanism of the esterification reaction you did.
3.
What characteristic absorption band changes would you expect in the IR spectrum on going from aspirin to salicyclic acid and
then to methyl salicylate as you did in the experiment today? Give approximate wavenumbers associated with each functional
group change.
What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What
other impurities are present in your product and how do you know?
Synthesis of ZybanⓇ:
1. Write a mechanism for the bromination of m-chloropropiophenone.
Br₂
CH2Cl2
Cl
Br
2. Give the expected m/z (to a round number) for the molecular ion from the product above (including isotopic peaks).
3. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What
other impurities are present in your product and how do you know?
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