An unknown compound is treated with HBr in the dark. The product of this reaction is reacted with potassium t-butoxide. The product of reaction 2 is treated with HBr and peroxide. In reaction 4 the product of reaction 3 is treated with lithium acetylenide (C2H-). The product of reaction4 is reduced with hydrogen using platinum as a catalyst. This final product was determined to be n-pentylcyclopentane. What is the name of the original unknown compound?

An unknown compound is treated with HBr in the dark. The product of this reaction is reacted with potassium t-butoxide. The product of reaction 2 is treated with HBr and peroxide. In reaction 4 the product of reaction 3 is treated with lithium acetylenide (C2H-). The product of reaction4 is reduced with hydrogen using platinum as a catalyst. This final product was determined to be n-pentylcyclopentane. What is the name of the original unknown compound?

Macroscale and Microscale Organic Experiments

7th Edition

ISBN:9781305577190

Author:Kenneth L. Williamson, Katherine M. Masters

Publisher:Kenneth L. Williamson, Katherine M. Masters

Chapter17: Nucleophilic Substitution Reactions Of Alkyl Halides

Section: Chapter Questions

Problem 3Q

See similar textbooks

Similar questions

An unknown compound is treated with HBr and peroxide. The product of this reaction is reacted with lithium acetylenide. In reaction 3, the product of reaction 2 is reduced with hydrogen using Pd on BaSO4 as catalyst. This product is reacted with ozone, then NaHSO3. The final product is 3-methylhexanal, shown below. What was the original compound? CHO
An unknown compound is treated with HBr in the dark. The product of this reaction is reacted with potassium t- butoxide. The product of reaction 2 is treated with HBr and peroxide. In reaction 4 the product of reaction 3 is treated with lithium acetylenide (C2H"). The product of reaction4 is reduced with hydrogen using platinum as a catalyst. This final product was determined to be n-pentylcyclopentane. What is the name of the original unknown compound? ABC T T T Arial 3 (12pt) Path: p Words:0
Cyclohexene (an alkene) is mixed with potassium permanagnate solution (KMnO4). What do you expect to observe? A. The mixture will turn purple as the permanganate is reduced by the alkene. B. The purple colour will disappear as the permanganate is reduced by the alkene. C. Nothing. Permanganate does not react with alkenes. D. The purple colour will disappear as the permanganate is oxidised by the alkene.
Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions -X티 Hö: H-O -CH3 -CH3 H30*
Two substitution products result from the reaction between 3-chloro-3-methyl-1- butene with sodium acetate (CH3COO – Na +) in acetic acid under SN1. Identify the products.
Which alkene reacts with a red-brown solution of bromine to form 1,2-dibromo-1-ethylcyclohexane.
Draw the two major organic products of the reaction in ether. Show the stereochemistry of the products. Are the products single enantiomers or racemic mixtures?
One compound that contributes to the “seashore smell” at beaches in Hawai‘i is dictyopterene D', a component of a brown edible seaweed called limu lipoa. Hydrogenation of dictyopterene D' with excess H2 in the presence of a Pd catalyst forms butylcycloheptane. Ozonolysis with O3 followed by (CH3)2S forms CH2(CHO)2, HCOCH2CH(CHO)2, and CH3CH2CHO. What are possible structures of dictyopterene D'?
Using Friedel Crafts alkylation of benzene, a group of scientists discovered compound A, C10H12O, an optically inactive compound. They discovered that compound B, C10H12ClO, is produced during the halogenation process. When compound B is reacted with nitric acid, compound C, C10H10ClNO3, is formed. While Friedel Crafts alkylation of compound A produced compound D. This compound D was oxidised to produce compound E, C11H12O3 as a major product. Compound F, C12H14O2, was produced by Friedel Crafts acylation of compound A. This compound F reacts positively with alkaline iodine and 2,4-dinitrophenylhydrazine. However, it returns negative results for Tollens' and Benedict's test. Prolonged heating of compound F with acidified potassium manganite (VII) produces compound G, C8H6O4 (aromatic dicarboxylic acid compound) as a major product and minor products (carbon dioxide and water). Identify the possible structural formulae compounds A to G. How would you distinguish between compounds E and…
When carbonyl compounds are reduced with a reagent such as LiAlH4 or NaBH4 and a new stereogenic center is formed, what will the composition of the product mixture be? Forms more of one enantiomer than another because of steric reasons around the carbonyl Forms more of one enantiomer than another depending on the temperature of the reaction Forms different products depending on the solvent used Forms a racemic mixture of the two possible enantiomers
CH3 CH3 Br- Br2 .CH3 CH2Cl2 CH3 H3C H3C Br Electrophilic addition of bromine, Brɔ, to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH,Cl,. In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CH3 CH3 CH3 CH3 H3C H3C :Br: :Br:
Addition of HBr to allene (CH2 = C = CH2) forms 2-bromoprop-1-ene rather than 3-bromoprop-1-ene, even though 3-bromoprop-1-ene is formed from an allylic carbocation. Considering the arrangement of orbitals in the allene reactant, explain this result.