Steroids are a class of organic compounds containing a specific tetracyclic skeleton (four rings), as seen in the compounds shown below. During efforts to synthesize a steroid that was isolated from the Atlantic starfish, the side chain of compound 1 was converted into the side chain of compound 2, as highlighted below. Propose a synthesis for this transformation. H,C H,C OH HC HC H. OAc = AcO AcO 2

Steroids are a class of organic compounds containing a specific tetracyclic skeleton (four rings), as seen in the compounds shown below. During efforts to synthesize a steroid that was isolated from the Atlantic starfish, the side chain of compound 1 was converted into the side chain of compound 2, as highlighted below. Propose a synthesis for this transformation. H,C H,C OH HC HC H. OAc = AcO AcO 2

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter15: An Introduction To Organometallic Compounds

Section15.1: Organomagnesium And Organolithium Compounds

Problem 15.2P: Recalling the reactions of alcohols from Chapter 10, show how to synthesize each compound from an...

See similar textbooks

Similar questions

Ketones and aldehydes react with sodium acetylide (the sodium salt of acetylene) to give alcohols, as shown in the following example: R, OH 1. HC=C: Na* 2. Hзо C. R2 R2 HC Draw the structure of the major reaction product when the following compound reacts with sodium acetylide, assuming that the reaction takes preferentially from the Re face of the carbonyl group. Use the wedge/hash bond tools to indicate stereochemistry where it exists. You do not have to explicitly draw H atoms. If a group is achiral, do not use wedged or hashed bonds on it.
Methyl isocyanate, CH3 -N= C = O, is used in the industrial synthesis of a type of pesticide and herbicide known as a carbamate. As a historical note, an industrial accident in Bhopal, India, in 1984 resulted in leakage of an unknown quantity of this chemical into the air. An estimated 200,000 people were exposed to its vapors, and over 2000 of these people died. Q.) Methyl isocyanate reacts with strong acids, such as sulfuric acid, to form a cation. Will this molecule undergo protonation more readily on its oxygen or nitrogen atom? In considering contributing structures to each hybrid, do not consider structures in which more than one atom has an incomplete octet
C22T03Q4426 Give the major product(s) of the following reaction. H -N-H NaOH CH,NH, H20 OH H. OMe H-N O O
OH CH3 CH3 CH3 The synthesis of this amine from acetophenone involves several reactions, one of which is shown below. Draw the structure(s) of the major organic product(s) of the following reaction: CH3 NH3, NABH;CN → product
If the following compound is saponified with sodium hydroxide, the products are: O || CH3(CH2) 14CH2-C-O-CH₂CH3 an ester and an alcohol an alcohol and a salt an acid and a salt an acid and an alcohol The purpose of the acid catalyst in the hydrolysis of an amide is: to enhance the nucleophilicity of the water molecule to enhance the electrophilicity of the amide carbonyl carbon to enhance the electrophilicity of the water molecule to shift the equilibrium of the reaction Which of the following compounds has the highest boiling point? CH3CH3 CH3CH2OH CH3-0-CH3 CH3COOH
A synthetic organic molecule, G, which contains both aldehyde and ether functional groups, is subjected to a series of reactions in a multi-step synthesis pathway. In the first step, G undergoes a Wittig reaction, leading to the formation of an alkene, H. Subsequently, H is treated with an ozone (O3) reagent followed by a reducing agent in an ozonolysis reaction, resulting in the formation of two different products, I and J. Considering the functional groups present in G and the nature of the reactions involved, what are the most probable structures or functional groups present in products I and J? A. I contains a carboxylic acid group, and J contains an aldehyde group. B. I contains a ketone group, and J contains an alcohol group. C. I and J both contain aldehyde groups. D. I contains an ester group, and J contains a ketone group. Don't use chat gpt.
Fill in thhe blanks with the appropriate chemical compound for the following reactions: 1-methylcyclohexanol + phosphoric acid catalyst + heat --> + 2-methylcyclohexanol + phosphoric acid catalyst + heat --> 3-methylcyclohexane 3-methylcyclohexene methylenecyclohexane| 2-methylcyclohexene 1-methylcyclohexene 1-methylcyclohexane Next pag ge MacBook Air
Draw the structure of the following organic compounds. ▪ 7-fluorohept-4-yn-2-ol 3-methoxycyclopent-3-en-1-one 5-ethyl-6-fluoro-7-propoxyhept-2-yne 5-amino-3,3-dimethylcyclohexan-1-one 3-ethoxy-N,N-diethyl-5-oxoheptanamide - ☐ ☐ ■ 1-ethoxy-3-ethyl-N-methylpent-4-en-2-araine 2-amino-5-fluorocyclopentane-1-carboxylic acid acetic 4-fluoro-3-hydroxy-2-methylpentanoic anhydride
A postgraduate student wanted to synthesized two carbonyl compounds known as compounds M and N using oxidation of alcohol. However, these carbonyl compounds should have more than 6 carbon atoms. Draw two (2) possible structural formulae for compounds M and N. How would you distinguish between compounds M and N?
Provide a mechanism for the following reaction. Show each step in your mechanism and use curved arrows to show the movement of electron pairs. Hint: the first step is a proton transfer; second step, nucleophilic attack. OCH3 H,SO4 CH;OH
In an advanced synthetic chemistry experiment, a researcher prepares a compound, ZY-7, by reacting a ketone (C5H10O) with hydroxylamine (NH2OH), followed by heating in the presence of an acid catalyst. The resulting compound, ZY-7, is then treated with a solution of sodium nitrite (NaNO2) and hydrochloric acid (HCl) at low temperature. Identify the class of compound that ZY-7 most likely belongs to after this series of reactions." A) Amide B) Oxime C) Nitro compound D) Diazonium salt E) Ester Don't use chatgpt please provide valuable answer
Identify the structure of 3-phenylpentane 1 ΠΙ CHÍCH,CH HẠCH CH a. I IV O > d. II IV. OH СЊСЊ СНСН СН V.