A dibromide loses only one bromine when it reacts with sodium hydroxide. The dibromide forms toluene (C6H5 - CH3) when it reacts with magnesium shavings in ether followed by treatment with dilute acid. Give possible structures for the dibromide.

A dibromide loses only one bromine when it reacts with sodium hydroxide. The dibromide forms toluene (C6H5 - CH3) when it reacts with magnesium shavings in ether followed by treatment with dilute acid. Give possible structures for the dibromide.

General, Organic, and Biological Chemistry

7th Edition

ISBN:9781285853918

Author:H. Stephen Stoker

Publisher:H. Stephen Stoker

Chapter14: Alcohols, Phenols And Ethers

Section: Chapter Questions

Problem 14.71EP: Three isomeric pentanols with unbranched carbon chains exist. Which of these isomers, upon...

See similar textbooks

Related questions

Q: Sabinene and A3-carene are isomeric natural products with the molecular formula C10H16. (a)…

A: The given compounds are,

Q: Describe a sequence of reactions by which 3-methyl-1-butyne can be straightforwardly prepared from…

Q: A certain compound of molecular formula C19H38 was isolated from fish oil and from plankton. On…

A: It is given that compound of molecular formula C19H38 gives 2,6,10,14-tetramethylpentadecane on…

Q: Using the normal/primary isomer of C4H10O, treat it with conc.H2SO4 and heat to produce A.…

A: The primary isomer of C4H10O must be a primary alcohol thus, C4H10O is butan-1-ol. The structure of…

Q: Give the structure of the major and minor organic products formed when HBr reacts with…

Q: Give the product structure of this reaction: - Explain through mechanisms the formation of this…

Q: Write the structure of the major organic product isolated from the reaction of 3-hexyne with (a)…

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

Q: (a) Chromic acid oxidation of 4-tert-butyl-1,2-dimethylbenzene yielded a single compound having the…

A: The compound C12H14O4 obtained by chromic acid oxidation of 4-tert-butyl-1,2-dimethylbenzene has to…

Q: 7. The following SN2 reaction yields a product with the given empirical formula. Suggest a structure…

Q: Compound A has the formula CioH16 On catalytic hydrogenation over palladium, it reacts with only one…

Q: The following reaction has been reported in the chemical literature and gives a single organic…

A: Alkene gives an electrophilic addition reaction with borane. Alkene reacts with BH3 and then NaOH…

Q: оо || || HÖCH,CH2CH2C-CH2CH2CH2ÖČH

A: A structure for hydrocarbon C10H14 has to be proposed.

Q: 1. In the reactions involving the three isomeric alcohols with the formula C4H9OH, describe what…

A: “Since you have asked multiple question, we will solve the first question for you. If you want any…

Q: A compound having the molecular formula C22H32O2 was isolated in 66% yield in the following…

A: Olefin metathesis 1-In olefin metathesis, two olefin compounds form a four-membered ring…

Q: An unknown hydrocarbon A with the formula C6H10 reacts with 1 molar equivalent of H2 over a…

Q: An unknown hydrocarbon decolorizes bromine in CCL4, and it undergoes catalytic reduction to give…

A: Applying concept of organic synthesis.

Q: Of the four possible cis,trans isomers, one is formed in over 85% yield. Q.) Which is the structure…

A: Given:

Q: 2 C,H9Lİ [C;H6 j* (Li*); 2 C4H10 | -

A: Ans

Q: 4. Compound CC is formed from the reaction of benzene with CH3;Cl in the presence of AICI3.…

A: (a. The structural formula of CC, EE, FF, GG and DD can be given as follows:…

Q: 5. An unknown hydrocarbon A with the formula C6H12 reacts with 1 molar equivalent of H2 over a…

A: The given unknown hydrocarbon A with formula C6H12reacts with 1 molar equivalent of H2 over a Pd…

Q: 3. Acetone, CH3(C=0)CH3, is known to all biologists because of its usefulness as a solvent and…

A: DBE of 1,1,3,3,5,5-hexamethyl trioxane = (C+1)+N/2-H/2-X/2 = (9+1)-18/2 = 10-9 = 1 When three…

Q: Alkenes can be hydrated to form alcohols by (1) hydroboration followed by oxidation with alkaline…

A: Hydration of given alkene to alcohol via hydroboration is first shown below,

Q: Give the structures of the substitution products expected when 1-bromohexane reacts with(a) NaOCH2CH

Q: Draw structural formulas for the alkene(s) formed by treatment of each haloalkane or halocycloalkane…

Q: Compound A, C10H180, undergoes a reaction with concentrated sulfuric acid under heat, to yield a…

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: 11. The following diagram represents a synthesis which begins with bromoethane. (i) (iii) C2HGO (C)…

A: The compound D is an ester formed by the alcohol C and the carboxylic acid B.

Q: O: C14H1206 maleic anhydride in excess

A: The reaction in which conjugated diene react with dienophile is known as Diels alder reaction.

Q: A certain unknown compound has the molecular formula C10H16. On catalytic hydrogenation with Pt,…

A: The degree of unsaturation in a compound can be calculated by : Degree of…

Q: Compound A has the formula CioH16 On catalytic hydrogenation over palladium, it reacts with only one…

A: Ozonolysis is an organic reaction shown by unsaturated alkenes and alkynes. The carbon-carbon…

Q: One of the constituents of turpentine is a-pinene, formula C10H16. The following scheme gives some…

Q: Stearolic acid, C18H32O2, yields stearic acid on catalytic hydrogenation and undergoes oxidative…

A: , From the given data, the structure of stearic acid is , R

Q: Compound A has the formula C„H and is known not to contain any triple 10 16 bonds. When treated with…

Q: The compound BD3 is a deuterated form of borane. Predict the product formed when 1-methylcyclohexene…

A: Given compound: 1-methylcyclohexene

Q: 1. In the reactions involving the three isomeric alcohols with the formula C4H9OH, describe what…

A: The reactivity of an alcohol is dependent upon the attachment of their functional hydroxyl group.…

Q: Compound X is optically inactive and has the formula C 16H 16Br 2. On treatment with strong base, X…

A: When alkyl halide is treated with a base, elimination reaction can occur. The elimination can either…

Q: The sex attractant of the housefly has the formula C23 H46. When treated with warm potassium…

A: Warm potassium permanganate splits double bond between carbon atoms and gives acid or carbonyl…

Q: Give the structures of the substitution products expected when 1-bromohexane reacts with(a)…

A: There are many mechanisms in organic chemistry such as nucleophilic substitution, nucleophilic…

Q: Compound A, C10H180, undergoes a reaction with concentrated sulfuric acid under heat, to yield a…

A: Organic reaction mechanisms.

Q: The following product is expected from the reaction of 3-heptyne with sodium metal in liquid…

Q: The sex attractant of the housefly has the formula C23H46. When treated with warm potassium…

A: Given: The molecular formula of the sex attractant of the housefly = C23H46 Two…

Q: Compound A (C7H11Br) is treated with magnesium in ether to give B (C7H11MgBr) which reacts violently…

A: The reaction of compound A with magnesium in ether to give compound B (C7H11MgBr) is given below.…

Q: Chhloropropane + sodium ethoxide in the presence of ethanol will yield what products (SN2 reaction).…

A: Nucleophilic substitution reactions are those reactions in which nucleophile attacks the alkyl…

Q: An unknown hydrocarbon A with the formula C6H12 reacts with 1 molar equivalent of H2 over a…

A: H2/of hydrogenate alkene into alkane. OsO4 adds two hydroxy group on the double bond via syn…

Q: Compound X, C,4H12Br2, is optically inactive. On treatment with strong base, X gives hydrocarbon Y,…

A: The compound formula = C14H12Br2 Degree of unsaturation (DBU) = 14 - (12÷2) - (2÷2) + 1= 8 Degree of…

Q: Compound EE, C5H10O gives a positive result (formation of silver mirror) when reacted with Tollen’s…

Q: Compound AA, C4H®O, gives a positive result (formation of a silver mirror) when reacted with…

A: Aldehydes, ketones, alcohols, carboxylic acids, etc. are different classes of compounds. Each of…

Q: Describe the ozonolysis of alkenes one mole of a hydrocarbon(A) reacts with one mole of beomine…

A: one mole of a hydrocarbon (A) reacts with one mole of bromine. So, the dibromo compound will have…

Q: An optically active monoterpene (compound A) with molecular formula C10H18O undergoes catalytic…

Concept explainers

Designing a Synthesis

Organic synthesis is a branch of chemical synthesis that involves the planned construction of organic compounds/molecules from smaller units that possess functional groups. Friedrich Wöhler was the first scientist who designed the synthesis of an organic compound, urea from inorganic starting materials silver cyanate with ammonium chloride via a simple, one-step synthesis.

Question

A dibromide loses only one bromine when it reacts with sodium hydroxide. The dibromide forms toluene (C₆H₅ - CH₃) when it reacts with magnesium shavings in ether followed by treatment with dilute acid. Give possible structures for the dibromide.

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

VIEW

Step 2

VIEW

Step 3

VIEW

Trending now

This is a popular solution!

Step by step

Solved in 3 steps with 2 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

A dibromide loses only one bromine when it reacts with sodium hydroxide. The dibromide forms toluene 1C6H5 @CH32 when it reacts with magnesiumshavings in ether followed by treatment with dilute acid. Give possible structures for the dibromide.
What is the major monosubstitution product from the Friedelâ€”Crafts reaction of benzene with 1 -chloro-2-methylpropane in the presence of AlCl3?
Three isomeric pentanols with unbranched carbon chains exist. Which of these isomers, upon dehydration at 180C, yields only 1-pentene as a product?
An optically active monoterpene (compound A) with molecular formula C10H18O undergoes catalytic hydrogenation to form an optically inactive compound with molecular formula C10H20O (compound B). When compound B is heated with acid, followed by reaction with O3 and then with dimethyl sulfide, one of the products obtained is 4-methylcyclohexanone. Give possible structures for compounds A and B.
Chhloropropane + sodium ethoxide in the presence of ethanol will yield what products (SN2 reaction). Show the configuration of the product as well as the structural formula
An unknown hydrocarbon A with the formula C6H10 reacts with 1 molar equivalent of H2 over a palladium catalyst to give B C6H12 (Rxn 1). Hydrocarbon A also reacts with OsO4 to give the glycol C (Rxn 2). A gives 5-oxohexanal on ozonolysis (Rxn 3). Draw the structures of A, B, and C. Give the reactions.
(a) Chromic acid oxidation of 4-tert-butyl-1,2-dimethylbenzene yielded a single compound having the molecular formula C12H14O4. What was this compound?(b) What product is expected from chromic acid oxidation of 2,3-dihydroindene?
Compound A has the formula C9H19Cl. B is a C9H19Br compound.A and B undergo base-promoted E2 elimination to give the same alkene C as the major product as well as different minor products.C reacts with one molar equivalent of hydrogen in the presence of a palladium catalyst to form 2,6-dimethylheptane.Addition of HCl to C yields A as the major product.Propose structures for A and B.
1. write out all the isomers of the compound with molecular formula C4H10O. 2. select the normal/primary isomer and treat it with conc.H2SO4 and heat to produce A. Identify the type of reaction 3. Treatment of A with HCl/H2O gives B and with cold KMnO4/ OH- gives C . Give the name and structures of A, B and C 4. Treatment of A with Hot KMnO4/OH- gives D followed by acidification of the mixture to give E. What is D and E ?
An unknown hydrocarbon decolorizes bromine in CCl4CCl4, and it undergoes catalytic reduction to give cis-decalin. When treated with warm, concentrated potassium permanganate, this compound gives cis-1,2-cyclohexanedicarboxylic acid. Propose a structure for the unknown compound.
α-Terpinene, C10H16, is a pleasant-smelling hydrocarbon that has been isolated from oil of marjoram. On hydrogenation over a palladium catalyst, α-terpinene reacts with 2 molar equivalents of H2 to yield a hydrocarbon, C10H20. On ozonolysis, followed by reduction with zinc and acetic acid, α-terpinene yields two products, glyoxal and 6-methyl-2,5- heptanedione. (a) How many degrees of unsaturation does a-terpinene have? (b) How many double bonds and how many rings does it have? (c) Propose a structure for a-terpinene.
As an example of a ver rare occurence, the following hydrocarbon reacts with two equivalents of butylithium to form a dianion of the formula [C8H6]2- . Propose a structure for this dianion and explain why this dianion forms so readily.