Compound A has the molecular formula C14H25Br and was obtained by the reaction of sodium acetylide with 1,12-dibromododecane. On treatment of compound A with sodium amide, compound B (C14H24) was obtained. Ozonolysis of compound B gave the diacid HO2C(CH2)12CO2H. Catalytic hydrogenation of compound B over Lindlar palladium gave compound C (C14H26), and hydrogenation over platinum gave compound D (C14H28). Further, C yielded O=CH(CH2)12CH=O on ozonolysis. Assign structures to compounds A through D so as to be consistent with the observed transformations.
Compound A has the molecular formula C14H25Br and was obtained by the reaction of sodium acetylide with 1,12-dibromododecane. On treatment of compound A with sodium amide, compound B (C14H24) was obtained. Ozonolysis of compound B gave the diacid HO2C(CH2)12CO2H. Catalytic hydrogenation of compound B over Lindlar palladium gave compound C (C14H26), and hydrogenation over platinum gave compound D (C14H28). Further, C yielded O=CH(CH2)12CH=O on ozonolysis. Assign structures to compounds A through D so as to be consistent with the observed transformations.
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...
Related questions
Question
Compound A has the molecular formula C14H25Br and was obtained by the
reaction of sodium acetylide with 1,12-dibromododecane. On treatment of
compound A with sodium amide, compound B (C14H24) was obtained. Ozonolysis
of compound B gave the diacid HO2C(CH2)12CO2H. Catalytic hydrogenation of
compound B over Lindlar palladium gave compound C (C14H26), and
hydrogenation over platinum gave compound D (C14H28). Further, C yielded
O=CH(CH2)12CH=O on ozonolysis. Assign structures to compounds A through D
so as to be consistent with the observed transformations.
Expert Solution
This question has been solved!
Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.
This is a popular solution!
Trending now
This is a popular solution!
Step by step
Solved in 6 steps with 5 images
Recommended textbooks for you
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY