A hydrocarbon, A, with formula C11H16 undergoes hydrogenation with Pd to give product B, C11H22, and with Lindlar's catalyst to give product C, C11H18. Ozonolysis leads to a mixture of products including cyclohexanone and 4-oxobutanoic acid. Treatment with sodium amide (NaNH2) followed by bromoethane gives compound D, C13H20. Draw possible structures for A, B, C, and D. Structure of product C H₂, Lindlar's Structure of A 1. NaNHz 2. CH3CH2Br [1] Structure of product D

A hydrocarbon, A, with formula C11H16 undergoes hydrogenation with Pd to give product B, C11H22, and with Lindlar's catalyst to give product C, C11H18. Ozonolysis leads to a mixture of products including cyclohexanone and 4-oxobutanoic acid. Treatment with sodium amide (NaNH2) followed by bromoethane gives compound D, C13H20. Draw possible structures for A, B, C, and D. Structure of product C H₂, Lindlar's Structure of A 1. NaNHz 2. CH3CH2Br [1] Structure of product D

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...

See similar textbooks

Related questions

Q: Reduction reaction of 1-phenylethanone with lithium aluminium hydride yields a racemic mixture of…

Q: The reaction of N−bromosuccinimide with 4−methyl−3−nitroanisole has been reported in the chemical…

A: N- bromosuccinimide gives free radical substitution at allylic position.

Q: Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing…

A: The attack of a ylide on a carbonyl compound is known as the Wittig reaction. In this reaction, the…

Q: Aldehydes and ketones undergo acid-catalyzed reaction with alcohols to yield hemiacetals, compounds…

Q: synthetic organic molecule, G, which contains both aldehyde and ether functional groups, is…

A: The objective of this question is to determine the functional groups present in the given structure.…

Q: 2,2-dimethyl-1-propanol

A: Since you have posted a question with multiple sub-parts, we will solve the first three subparts for…

Q: Show how ethyl alcohol could be used to prepare (a) CH3CN and (b) CH3CH2CN. Along with ethyl alcohol…

A: Ethyl alcohol can be used for the preparation of acetonitrile (CH3CN) and propionitrile (CH3CH2CN),…

Q: Hydrocarbon A has the formula CgH12 and absorbs 3 equivalents of H₂ to yield B, C9H18, when…

A: Given: Hydrocarbon A has the formula C9H12 and absorbs 3 equivalents of H2 to yield B, C9H18, when…

Q: On being heated with a solution of sodium ethoxide in ethanol, compound A (C7H15Br) produced a…

Q: Alpha-phellandrene, C10H16, is a pleasant-smelling chiral compound that may be obtained from the…

A: Phellandrene is a cyclic monoterpene, widely spread in nature. Phellandrene was isolated from…

Q: Devise a route to convert propene to propanone. Specify, in order, the reagents you would use. The…

A: The question is based on the concept of organic synthesis.We need to synthesize the product using…

Q: Compound A, C 10H 18O, undergoes reaction with dilute H 2SO 4 at 50 °C to yield a mixture of two…

A: The organic compound can be nucleophilic (rich in electron density), or electrophilic…

Q: Draw a structural formula for the cycloalkene with the molecular formula C6H10 that reacts with Cl2…

A: Introduction: Halogenation reaction: In halogenation reaction, halides are added to the unsaturated…

Q: 3.) Starting from phenol, the synthesis of 2,4-dichlorophenoxyacetic acid involves four steps…

Q: Propose two different methods to synthesize oct-1 -en-3-ol [CH3(CH2)4CH(OH)CH = CH2] using a…

A: The reaction of a Grignard reagent with a carbonyl compound produces alcohols. The general reaction…

Q: Consider the compound C5H9B (Compound X). It reacts with potassium tert-butoxide to give Compound Y,…

Q: Draw a structural formula for the alkene with the molecular formula C-H₁0 that reacts with Br, and…

Q: Benzene can be hydroxylated by treating it with hydrogen peroxide and a strong acid such as…

A: Given reaction:

Q: Holot CH3 H3C Ph₂p-CHCH3 Aldehydes and ketones are converted into alkenes by means of a direct…

A: Triphenylphosphine (PPh3) can react with ethyl bromide (C2H5Br) via a nucleophilic substitution…

Q: Sharpless epoxidation of allylic alcohol X forms compound Y. Treatment of Y with NaOH and C6H5SH in…

Question

K
H2,
Lindlar's
Structure of
A
H2, Pd/C
Structure of
product B
Problem 13 of 14
1. NaNH2
2.
CH3CH2Br
Submit
Structure of
product D
Version: 3.115.30 + 4493 production

Structure of
product C
A hydrocarbon, A, with formula C11H16
undergoes hydrogenation with Pd to give
product B, C11H22, and with Lindlar's
catalyst to give product C, C11 H18.
Ozonolysis leads to a mixture of
products including cyclohexanone and
4-oxobutanoic acid. Treatment with
sodium amide (NaNH2) followed by
bromoethane gives compound D, C13H20.
Draw possible structures for A, B, C, and
D.
H₂,
Lindlar's
Problem 13 of 14
Structure of
A
1. NaNH2
Submit
2.
CH3CH₂Br
Structure of
product D

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!

SEE SOLUTION Check out a sample Q&A here

Step 1: Introduce question

VIEW

Step 2: Explain reaction pathway

VIEW

Solution

VIEW

Trending now

This is a popular solution!

Step by step

Solved in 3 steps with 1 images

SEE SOLUTION Check out a sample Q&A here

Knowledge Booster

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

Compound X has the formula CgH12. X reacts with two molar equivalents of hydrogen in the presence of a palladium catalyst to form cyclooctane. Treatment of X with ozone followed by zinc in aqueous acid gives two molar equivalents of the same dialdehyde. What is the structure of X? • In cases where there is more than one answer, just draw one. coll ChemDoodleⓇ 26
Alpha-phellandrene, C₁0H₁6, is a pleasant-smelling chiral compound that may be obtained from the leaves of eucalyptus trees. It has the molecular formula C₁0H16 and a UV absorption maximum at 263 nm. On hydrogenation with a palladium catalyst, an achiral hydrocarbon with the formula C₁0H20 is obtained. Ozonolysis of alpha-phellandrene, followed by treatment with zinc and acetic acid, produces the following two compounds: 0 || CH3C-CH 0 || ● Propose a structure for alpha-phellandrene. (+ || HCCH₂CHCH I CH(CH3)2 • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. n [ ]# ?
When 2-iodo-1,4-dimethylcyclohexane is heated in acetic acid, CH3COOH, a mixture of substitution and elimination products is obtained. Provide structures for all possible products, writing [not drawing] the name of the mechanism by which each one is formed.
Compound A, CH10, was found to be an optically active alcohol. Despite its apparent unsaturation, no hydrogen was absorbed on catalytic reduction over a Pd/C catalyst. On treatment of A with dilute H,SO, dehydration occurred and an optically inactive alkene B, CH4 was produced as the major product. Alkene B, on ozonolysis, gave two products. Product C, C,H,0, was shown to be an aldehyde while product D, CHg0, was shown to be a ketone. Draw the structure of compound C. • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. In cases where there is more than one answer, jtust draw one.
If phenoxide ion is allowed to react with 1-bromopentane, pentyl phenyl ether is obtained. However, if cyclohexane is used as the alkyl halide, the major products are phenol and cyclohexene. Explain how these products were formed.
The reaction of Compound X and PCC yielded an aldehyde as the product. What is the identity of CompoundX: cyclohexanol or 1-pentanol?
(S)-2-butanol reacts with potassium dichromate (K2CrO4) in aqueous sulfuric acid to give A(C4H3O). Treatment of A with ethylmagnesium bromide in anhydrous ether gives B(C,H140). Draw the structure of B.