Experiment 10: Acid-Catalyzed Hydration of Norbornene via Sublimation

Question 1

A dehydration reaction was done starting with 2.00 g of 2-butanol. The data collected after the reaction is shown below.
GC Integration:
Alkene 1- 65.43
Alkene 2 - 46.02
Alkene 3 - 13.25
Total mass of alkene products = 1.3 g
Molar mass of alkenes - 84.12 g/mol

How many grams of each alkene 1, 2, and 3 were produced?

Answer 1

alkene 1 = 0.68 g
alkene 2 = 0.48 g
alkene 3 = 0.14 g

Question 2

diagram Q2 Lab 10 Uria

Answer 2

?

Question 3

! Hydration of norbornene yields norborneol. How would the yield of norborneol product(s) be affected if the alcohol(s) was/were left under vacuum for an excessive period of time to remove all traces of solvent?

Answer 3

The yield would be lower, because some of the product would be removed.

NOT The yield would stay the same.

Question 4

Why is sulfuric acid a superior acid to HCl for affecting the acid-catalyzed hydration of alkenes?

Answer 4

Sulfuric acid is non-nucleophilic and therefore doesn’t cause undesirable products.

Question 5

Norbornene is hydrated to norborneol products. How will determine which product (exo or endo norborneol) you obtained?

Answer 5

melting point

Question 6

What type of reactive intermediate is formed in the reaction of an alkene with H2O and H2SO4 to give an alcohol?

Answer 6

carbocation

Question 7

The dehydration of 2-butanol gives a mixture of possible alkene products. One alkene was determined to be the “major” product. Which alkene was expected to be generated in the highest yield?

Answer 7

trans-2-butene

Question 8

Which of the following statements is/are FALSE concerning today’s reaction shown below?
I. Infrared spectroscopy could be used to distinguish the 2 possible products.
II. An alkene is being transformed into an alcohol
III. Water is the electrophile

Answer 8

Only I & III are FALSE

Question 9

What is the relationship between the exo and endo products of the acid-catalyzed hydration reaction of norbornene (forming exo and endo norborneol)?

Answer 9

diastereomers

Question 10

What is the number of chiral centers present in a norborneol molecule?

Answer 10

3

Question 11

! Which of the following statement(s) is/are TRUE?
I. Diastereomers can be differentiated by melting point.
II. Norbornene is an example of a solid with a high vapor pressure at room temperature (it sublimes).
III. Sulfuric acid will act as both a catalyst and nucleophile in the hydration of norbornene.

Answer 11

Only I & II are TRUE

I. Diastereomers can be differentiated by melting point.
II. Norbornene is an example of a solid with a high vapor pressure at room temperature (it sublimes).

Question 12

After the addition of NaOH to the norbornene reaction medium, the following species are left in the solution (considering that the reaction may not have gone to completion):
norborneol, water, NaHSO4, norbornene

You are then instructed to transfer the solution to a separatory funnel and extract it twice with 3-4 mL portions of dichloromethane. Which of the above components will dissolve into the dichloromethane layer?

Answer 12

Norborneol and water

Question 13

Notice that the acid-catalyzed hydration of norbornene to norborneol is an equilibrium process. What reaction conditions favor an addition reaction?

Answer 13

Increase the amount of water