1. Refer to the dehydration reaction given below involving 2-butanol and answer the questions that follow. OH H,SO CH;-CH,-CH-CH + S R i) The boiling point of 2-butanol is higher than butane. Give a reason for the difference in the boiling points of the two compounds. ii) The dehydration of 2-butanol yields two products R and S. Write the structure of the two products formed. Identify the major product. Explain the reason for your choice of the major product.

Chemistry: An Atoms First Approach
2nd Edition
ISBN:9781305079243
Author:Steven S. Zumdahl, Susan A. Zumdahl
Publisher:Steven S. Zumdahl, Susan A. Zumdahl
Chapter21: Organic And Biological Molecules
Section: Chapter Questions
Problem 7RQ
icon
Related questions
Question
1. Refer to the dehydration reaction given below involving 2-butanol and answer the questions that
follow.
OH
H,SO,
CH;-CH,-CH-CH3
R + S
i) The boiling point of 2-butanol is higher than butane. Give a reason for the difference in the boiling
points of the two compounds.
ii) The dehydration of 2-butanol yields two products R and S. Write the structure of the two products
formed. Identify the major product. Explain the reason for your choice of the major product.
2. Indicate which is the stronger acid. Explain your choice clearly.
H3C-CH-CH2 OH
H3C-CH2 CH2OH
or
F
3. Give the IUPAC names of molecules
CH3
H3C-CH-CH2 CH-CH-CH3
Br
4. A student was asked to prepare an alkene X in high yield using any alcohol as starting material
CH3
CH;-C-
-CH=CH2
CH3
X
He chose 3, 3-dimethylbutan-2-ol (XI) and carried out a dehydration reaction. He was however
horrified to note that the only alkene obtained was XII.
CH3
ОН
CH3
conc. H,SO4
CH-CH3
CH;-C=C-CH3
heat
CH3
CH3
XI
XII
i) Explain what went wrong here, and why X could not be formed from 3, 3-dimethylbutan-2-ol. Use
structures to help support your answer.
ii) Give an equation to show a much better method for preparing X in high yield.
Transcribed Image Text:1. Refer to the dehydration reaction given below involving 2-butanol and answer the questions that follow. OH H,SO, CH;-CH,-CH-CH3 R + S i) The boiling point of 2-butanol is higher than butane. Give a reason for the difference in the boiling points of the two compounds. ii) The dehydration of 2-butanol yields two products R and S. Write the structure of the two products formed. Identify the major product. Explain the reason for your choice of the major product. 2. Indicate which is the stronger acid. Explain your choice clearly. H3C-CH-CH2 OH H3C-CH2 CH2OH or F 3. Give the IUPAC names of molecules CH3 H3C-CH-CH2 CH-CH-CH3 Br 4. A student was asked to prepare an alkene X in high yield using any alcohol as starting material CH3 CH;-C- -CH=CH2 CH3 X He chose 3, 3-dimethylbutan-2-ol (XI) and carried out a dehydration reaction. He was however horrified to note that the only alkene obtained was XII. CH3 ОН CH3 conc. H,SO4 CH-CH3 CH;-C=C-CH3 heat CH3 CH3 XI XII i) Explain what went wrong here, and why X could not be formed from 3, 3-dimethylbutan-2-ol. Use structures to help support your answer. ii) Give an equation to show a much better method for preparing X in high yield.
Expert Solution
steps

Step by step

Solved in 2 steps with 1 images

Blurred answer
Knowledge Booster
General Physical Properties of Organic Compounds
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Chemistry: An Atoms First Approach
Chemistry: An Atoms First Approach
Chemistry
ISBN:
9781305079243
Author:
Steven S. Zumdahl, Susan A. Zumdahl
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781133611097
Author:
Steven S. Zumdahl
Publisher:
Cengage Learning