menu
bartleby
search
close search
Hit Return to see all results
close solutoin list

Compound A , C 11 H 16 O, was found to be an optically active alcohol. Despite its apparent unsaturation, no hydrogen was absorbed on catalytic reduction over a palladium catalyst. On treatment of A with dilute sulfuric acid, dehydration occurred and an optically inactive alkene B , C 11 H 14 , was the major product. Alkene B , on ozonolysis, gave two products. One product was identified as propanal, CH 3 CH 2 CHO. Compound C , the other product, was shown to be a ketone, C 8 H 8 O. How many degrees of unsaturation does A have? Write the reactions, and identify A , B , and C .

BuyFindarrow_forward

Organic Chemistry

9th Edition
John E. McMurry
Publisher: Cengage Learning
ISBN: 9781305080485

Solutions

Chapter
Section
BuyFindarrow_forward

Organic Chemistry

9th Edition
John E. McMurry
Publisher: Cengage Learning
ISBN: 9781305080485
Chapter 8.SE, Problem 72AP
Textbook Problem
236 views

Compound A , C11H16O, was found to be an optically active alcohol. Despite its apparent unsaturation, no hydrogen was absorbed on catalytic reduction over a palladium catalyst. On treatment of A with dilute sulfuric acid, dehydration occurred and an optically inactive alkene B , C11H14, was the major product. Alkene B , on ozonolysis, gave two products. One product was identified as propanal, CH3CH2CHO. Compound C , the other product, was shown to be a ketone, C8H8O. How many degrees of unsaturation does A have? Write the reactions, and identify A , B , and C .

Interpretation Introduction

Interpretation:

Given an optically active alcohol, A has the molecular formula C11H16O. It does not adsorb any hydrogen during catalytic reduction in the presence of Pd. It gets dehydrated when treated with dilute sulphuric acid to yield an optically inactive alkene, B (C11H14). The alkene B yields propanol, CH3CH2CHO and a ketone, C (C8H8O). The number of degrees of unsaturation in A is to be calculated. A, B and C are to be identified and the reactions are to be written.

Concept introduction:

The degree of unsaturation in a compound can be calculated by considering the molecular formula of the compound and its parent hydrocarbon. Any compound with a chiral centre will be optically active. Alcohols undergo dehydration when warmed with dilute sulphuric acid. During ozonolysis the double bond is cleaved to yield carbonyl compounds. If the doubly bonded carbon is disubstituted then ketones are produced and if the doubly bonded carbon is monoisubstituted then aldehydes are produced.

To calculate:

The number of degrees of unsaturation in compound A.

To identify:

The structures of compounds A, B and C.

To write:

The reactions given.

Explanation of Solution

The molecular formula of the compound A is C11H16O. The molecular formula of the corresponding parent hydrocarbon is C11H24.Thus the compound A has eight hydrogens less than the parent. Hence the degree of unsaturation in A is four. If the double bonds present in an aromatic ring are not hydrogenated in the presence of Pd. So the compound has a benzene ring which accounts for the four degrees of unsaturation. Alcohols when warmed with dilute sulfuric acid lose a molecule of water to yield an alkene...

Still sussing out bartleby?

Check out a sample textbook solution.

See a sample solution

The Solution to Your Study Problems

Bartleby provides explanations to thousands of textbook problems written by our experts, many with advanced degrees!

Get Started

Chapter 8 Solutions

Organic Chemistry
Show all chapter solutions
add
Ch. 8.5 - Tho following cycloalkene gives a mixture of two...Ch. 8.6 - What product would you obtain from catalytic...Ch. 8.7 - What product would you expect from reaction of...Ch. 8.7 - Starting with an alkene, how would you prepare...Ch. 8.8 - What products would you expect from reaction of...Ch. 8.8 - Propose structures for alkenes that yield the...Ch. 8.9 - What products would you expect from the following...Ch. 8.13 - What products are formed from acid-catalyzed...Ch. 8.13 - What products are formed from hydration of...Ch. 8.SE - Name the following alkenes, and predict the...Ch. 8.SE - Draw the structures of alkenes that would yield...Ch. 8.SE - The following alkene undergoes...Ch. 8.SE - From what alkene was the following 1, 2-diol made,...Ch. 8.SE - Predict the products for the following reactions,...Ch. 8.SE - Predict the products for the reactions in Problem...Ch. 8.SE - Draw the structures of the organoboranes formed...Ch. 8.SE - m-CPBA is not the only peroxyacid capable of...Ch. 8.SE - Provide the mechanism and products for the...Ch. 8.SE - Propose a curved-arrow mechanism to show how ozone...Ch. 8.SE - Which of the reactions below would result in a...Ch. 8.SE - Reaction of 2-methylpropene with CH3OH in the...Ch. 8.SE - Iodine azide, IN3, adds to alkenes by an...Ch. 8.SE - 10-Bromo- α -chamigrene, a compound isolated from...Ch. 8.SE - Isolated from marine algae, prelaureatin is...Ch. 8.SE - Dichlorocarbene can be generated by heating sodium...Ch. 8.SE - Reaction of cyclohexene with mercury(II) acetate...Ch. 8.SE - Use your general knowledge of alkene chemistry to...Ch. 8.SE - Treatment of 4-penten-l-ol with aqueous Br2 yields...Ch. 8.SE - Hydroboration of 2-methyl-2-pentene at 25°C,...Ch. 8.SE - Predict the products of the following reactions...Ch. 8.SE - Suggest structures for alkenes that give the...Ch. 8.SE - Predict the products of the following reactions,...Ch. 8.SE - Which reaction would you expect to be faster,...Ch. 8.SE - What product will result from...Ch. 8.SE - The cis and trans isomers of 2-butene give...Ch. 8.SE - Predict the products of the following reactions....Ch. 8.SE - Addition of HCl to 1-methoxycyclohexene yields...Ch. 8.SE - How would you carry out the following...Ch. 8.SE - Draw the structure of an alkene that yields only...Ch. 8.SE - Show the structures of alkenes that give the...Ch. 8.SE - In planning the synthesis of one compound from...Ch. 8.SE - Which of the following alcohols could not be made...Ch. 8.SE - Plexiglas, a clear plastic used to make many...Ch. 8.SE - Poly(vinyl pyrrolidone), prepared from...Ch. 8.SE - When a single alkene monomer, such as ethylene, is...Ch. 8.SE - Compound A has the formula C10HI6. On catalytic...Ch. 8.SE - An unknown hydrocarbon A with the formula C6H12...Ch. 8.SE - Using an oxidative cleavage reaction, explain how...Ch. 8.SE - Compound A, C10H18O, undergoes reaction with...Ch. 8.SE - Draw the structure of a hydrocarbon that absorbs 2...Ch. 8.SE - Simmons-Smith reaction of cyclohexene with...Ch. 8.SE - The sex attractant of the common housefly is a...Ch. 8.SE - Compound A has the formula C8H8. It reacts rapidly...Ch. 8.SE - How would you distinguish between the following...Ch. 8.SE - α-Terpinene, C10H16, is a pleasant-smelling...Ch. 8.SE - Evidence that cleavage of 1, 2-diols by HIO4...Ch. 8.SE - Reaction of HBr with 3-methylcyclohexene yields a...Ch. 8.SE - We’ll see in the next chapter that alkynes...Ch. 8.SE - Hydroxylation of cis-2-butene with 0s04 yields a...Ch. 8.SE - Compound A, C11H16O, was found to be an optically...

Additional Science Textbook Solutions

Find more solutions based on key concepts
Show solutions add
Give the IUPAC name for each of the following: a. b c.

Chemistry for Today: General, Organic, and Biochemistry

In what way has biotechnology had an impact on agriculture in the United States?

Human Heredity: Principles and Issues (MindTap Course List)

The bladder straddles the cardiovascular system and filters the blood. T F

Nutrition: Concepts and Controversies - Standalone book (MindTap Course List)

What does the size of the star image in a photograph tell you?

Horizons: Exploring the Universe (MindTap Course List)

The radius of a uniform solid sphere is measured to be (6.50 0.20) cm, and its mass is measured to be (1.85 0...

Physics for Scientists and Engineers, Technology Update (No access codes included)