A hydration reaction is performed using 150 mg norbornene, 0.25 mL H20, and 0.5 mL H2SO4. Then buffered with 3.5 mL 6M NaOH. Products are eco-norborneol and endo-norborneol.  draw the mechanisms for this reaction and identify any major/minor/racemic products, the theoretical yield, and limiting reactant

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Chapter20: Nucleophilic Substitution Reactions: Competing Nucleophiles
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A hydration reaction is performed using 150 mg norbornene, 0.25 mL H20, and 0.5 mL H2SO4. Then buffered with 3.5 mL 6M NaOH. Products are eco-norborneol and endo-norborneol. 

draw the mechanisms for this reaction and identify any major/minor/racemic products, the theoretical yield, and limiting reactant.

Therefore, the nature of the product(s) and orientation of the addition will be deter-
mined using gas chromatography. An alternate method of analysis is to measure the
refractive index of the product.
fosc
11
2-ethyl-1-butene
18
1.
2.
+
+
H₂O
Hg(O₂CCH3)2
In Parts B and C, dilute acid treatment of the bicyclic alkene, norbornene, will be
investigated to determine which of two stereoisomeric products is formed. In this case,
the regiochemistry of addition is the same for both products, but the stereoselectivity of
addition could result in either product depending upon the mechanism of addition.
Hydration could produce either exo-norborneol or endo-norborneol or both products.
diethyl
ether
H₂SO4
MO
H₂O
-ОН
H
exo-norborneol
mp 124-126°C
NaBH4
Na
+
Prelab Assignment
1. Determine the limiting reagent in your experiment.
2. Write a flow scheme for the experiment and workup procedure.
Experimental Procedure
Do not
OH
3-methyl-3-pentanol 2
bp 123°C
In this instance, the melting behavior of the two alcohols is distinctive. Isolation of
the product and determination of the melting point permit a definitive analysis of the
product to determine if the hydroxyl group is on the "top side" of the molecule (exo-
norborneol) or the "bottom side" (endo-norborneol).
-H
OH
endo-norborneol
mp 149-151°C
Wear eye protection at all times in the laboratory.
Sulfuric acid is a corrosive oxidizer. Mercuric acetate is a highly toxic and corro-
sive solid. Sodium borede is a corrosive solid. Wear gloves to avoid skin con-
their solutions.
tact with these comp
3. Work in a hood or
stilate
+
Sa
Transcribed Image Text:Therefore, the nature of the product(s) and orientation of the addition will be deter- mined using gas chromatography. An alternate method of analysis is to measure the refractive index of the product. fosc 11 2-ethyl-1-butene 18 1. 2. + + H₂O Hg(O₂CCH3)2 In Parts B and C, dilute acid treatment of the bicyclic alkene, norbornene, will be investigated to determine which of two stereoisomeric products is formed. In this case, the regiochemistry of addition is the same for both products, but the stereoselectivity of addition could result in either product depending upon the mechanism of addition. Hydration could produce either exo-norborneol or endo-norborneol or both products. diethyl ether H₂SO4 MO H₂O -ОН H exo-norborneol mp 124-126°C NaBH4 Na + Prelab Assignment 1. Determine the limiting reagent in your experiment. 2. Write a flow scheme for the experiment and workup procedure. Experimental Procedure Do not OH 3-methyl-3-pentanol 2 bp 123°C In this instance, the melting behavior of the two alcohols is distinctive. Isolation of the product and determination of the melting point permit a definitive analysis of the product to determine if the hydroxyl group is on the "top side" of the molecule (exo- norborneol) or the "bottom side" (endo-norborneol). -H OH endo-norborneol mp 149-151°C Wear eye protection at all times in the laboratory. Sulfuric acid is a corrosive oxidizer. Mercuric acetate is a highly toxic and corro- sive solid. Sodium borede is a corrosive solid. Wear gloves to avoid skin con- their solutions. tact with these comp 3. Work in a hood or stilate + Sa
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