Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 24, Problem 31P
Treatment of cyclohexene with
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Compounds A and B are isomers of the molecular formula C9H19Br. Both yield the same alkene C in an elimination reaction. Hydrogenation of C yields the product 2,3,3,4 tetramethyl pentane. What are the structures of A, B, and C?
Compound A is unsaturated hydrocarbon with molecular formula (C6H12)
reacted with Br2 in water to form compound B. compound C was produced
from the reaction between compound A, sulphuric acid and H2O (g).
Compound A undergo hydrogenation to form compound D. Compound E was
produced from the reaction of compound A with Br2 in room temperature.
Compound A undergo hydrohalogenation in the presences of hydrogen
peroxide to form compound F. The reaction between compound F with
aqueous sodium hydroxide will form compound G. Compound H was
produced when compound F reacts with the aqueous ammonia in ethanol.
Compound F also reacts with aqueous sodium cyanide to produce compound
I.
Draw the possible structural formulae of compounds A, B, C, D, E, F, G, H
and I.
Give the IUPAC nomenclature of compounds H and I.
Distinguish between compound A and D.
There are two compounds with the formula C3H6, one of which does not have a multiple bond. Draw its structure and explain why it is much less stable than the isomer with the double bond.
Chapter 24 Solutions
Organic Chemistry (6th Edition)
Ch. 24.1 - Prob. 1PCh. 24.1 - Prob. 2PCh. 24.1 - Prob. 3PCh. 24.2 - Prob. 4PCh. 24.2 - Prob. 5PCh. 24.4 - Problem 26.10
What reagents are needed to convert...Ch. 24.5 - Problem 26.11
What product is formed when each...Ch. 24.5 - Prob. 13PCh. 24.6 - Problem 26.13
Draw the products formed when each...Ch. 24.6 - Problem 26.14
What products are formed when ...
Ch. 24 - 26.19 What product is formed by ring-closing...Ch. 24 - 26.20 Draw the products formed in each...Ch. 24 - What organic halide is needed to convert lithium...Ch. 24 - 26.22 How can you convert ethynylcyclohexane to...Ch. 24 - 26.23 What compound is needed to convert styrene...Ch. 24 - 26.24 What steps are needed to convert to octane...Ch. 24 - Prob. 27PCh. 24 - 26.27 Draw the products (including stereoisomers)...Ch. 24 - 26.28 Treatment of cyclohexene with and forms...Ch. 24 - Prob. 32PCh. 24 - 26.30 What starting material is needed to prepare...Ch. 24 - Prob. 37PCh. 24 - Prob. 38PCh. 24 - When certain cycloalkenes are used in metathesis...Ch. 24 - 26.34 Draw the products formed in each reaction.
...Ch. 24 - Prob. 41PCh. 24 - Draw a stepwise mechanism for the following...Ch. 24 - Sulfur ylides, like the phosphorus ylides of...Ch. 24 - Although diazomethane is often not a useful...Ch. 24 - Prob. 46PCh. 24 - Prob. 47PCh. 24 - 26.45 Devise a synthesis of each compound from...Ch. 24 - 26.46 Devise a synthesis of each substituted...Ch. 24 - Biaryls, compounds containing two aromatic rings...
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- Draw the structure and give the molecular formula for a compound(a) 1-ethyl-3-methylcycloheptanearrow_forwardA compound with formula C7H12O is treated with sodium borohydride in methanol to yield 2,2-dimethylcylopentanol. Write a reaction scheme showing the structures of the reactant, the reagents, and the product. Will the product be optically active? Explain.arrow_forwardCompound A has the molecular formula C7H12. Hydrogenation of compound A produces 2-methylhexane. Hydroboration-oxidation of compound A produces an aldehyde. Draw the structure of compound A.arrow_forward
- Compounds X and Y are stereoisomers having the formula C6H12.Both X and Y react with one molar equivalent of hydrogen in the presence of a palladium catalyst to form hexane, and they each react with HBr to give a single bromoalkane product.Draw structural formulas for both X and Y.arrow_forwardAn unknown compound A is known to be an alcohol with themolecular formula C4H10O. When dehydrated, compoundA gave only one alkene product, C4H8, compound B. Compound A could not be oxidized. What are the identitiesof compound A and compound B? Draw structures and explain.arrow_forwardThere are 17 possible alkene isomers with the formula C6H12. Draw structures of the five isomers in which the longest chain has six carbon atoms, and give the name of each. Are any of these isomers chiral? (There are also eight isomers in which the longest chain has five carbon atoms, and four isomers in which the longest chain has four carbon atoms. How many can you find?)arrow_forward
- Catalytic cracking is an industrial process used to convert high-molecular-weight hydrocarbons to low-molecular-weight hydrocarbons. A petroleum company has a huge supply of heating oil stored as straight-chain C17H36, and demand has picked up for shorter chain hydrocarbons to be used in formulating gasoline. The company uses catalytic cracking to create the shorter chains necessary for gasoline. If they produce two molecules in the cracking, and 1-octene is one of them, what is the formula of the other molecule produced? As part of your answer, draw the condensed structural formula of the 1-octene.arrow_forwardWrite Lewis structures and describe the molecular geometry at each carbon atom in the following compounds:(a) cis-3-hexene(b) cis-1-chloro-2-bromoethene(c) 2-pentyne(d) trans-6-ethyl-7-methyl-2-octenearrow_forward2,2,3,3-Tetrabromopentane can be prepared by an addition reaction of excess Br2 with an alkyne. Draw the structure of the alkyne and name it.arrow_forward
- Reaction of (CH3)3CH with Cl2 forms two products: (CH3)2CHCH2Cl (63%) and (CH3)3CCl (37%). Why is the major product formed by cleavage of the stronger 1° C–H bond?arrow_forwardGlucose, C6H12O6, contains an aldehyde group but exist predominantly in the form of the cyclic hemiacetal show below. A cyclic hemiacetal is formed when the —OH group of one carbon bonds to the carbonyl group of another carbon. Identify which carbon provides the —OH group and which provides the —CHO? Give a functional isomer of glucose and draw its structure.arrow_forwardCompound X (structure shown below) has a molecular formula C5H1o and reacts with H2/Pt to give compound Y, C5H12. What is the name of the reaction involved to produce Compound Y? H2C H3C CH3 Hydration Hydrogenation Halogenation Addition of halohydrinarrow_forward
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