What do you expect the most prominent features to be in the IR spectra of the reactant and product? Compare the relative base strengths of the hydride ion and the alkoxide ion, and explain what each of the workup steps (i.e. after the initial reaction with NaBH4) does.

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
icon
Related questions
Question

borohydride reduction

What do you expect the most prominent features to be in the IR spectra of the reactant and product?

Compare the relative base strengths of the hydride ion and the alkoxide ion, and explain what each of the workup steps (i.e. after the initial reaction with NaBH4) does.

 

 

Important information of the experiment

 

500 L of 1-naphthaldehyde was added to a 10 mL round bottom flask along with 3.0 mL of methanol. This mixture was stirred until the aldehyde was dissolved in the methanol. This flask was placed in an ice bath and 100 mg of NaBH4 was added in 2-3 portions (weighed out in a small tube) over a few minutes. Stop the addition if excessive bubbling is observed. The flask is removed from the ice bath and is allowed to come to room temperature and stirred for 10 minutes. The borate ester is hydrolyzed by treating with 2.5 mL of 3 M NaOH. The resultant solution may be cloudy. Add 1-2 mL of water until you see a defined upper organic layer. Remove as much of the top layer as possible and place in a small clean dry test tube. Extract the remaining solution twice with dichloromethane (2x 1mL) removing the lower organic layer each time and combining it with the top layer originally removed. Dry the dichloromethane extracts by filtering the solution through a pipette containing anhydrous magnesium sulfate and sand. Filter this mixture into a clean dry beaker and evaporate the dichloromethane solution in the hood using a hot plate set to very low heat and agitating the mixture frequently.

Expert Solution
steps

Step by step

Solved in 4 steps with 1 images

Blurred answer
Knowledge Booster
Analyzing and Predicting Spectroscopic Data
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
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY