PKG ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259963667
Author: SMITH
Publisher: MCG
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Chapter 26, Problem 26.28P
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 26 Solutions
PKG ORGANIC CHEMISTRY
Ch. 26 - Prob. 26.1PCh. 26 - Prob. 26.2PCh. 26 - Prob. 26.3PCh. 26 - Prob. 26.4PCh. 26 - Prob. 26.5PCh. 26 - Prob. 26.6PCh. 26 - Prob. 26.7PCh. 26 - Problem 26.8
What starting materials are needed to...Ch. 26 - Prob. 26.9PCh. 26 - Problem 26.10
What reagents are needed to convert...
Ch. 26 - Problem 26.11
What product is formed when each...Ch. 26 - Prob. 26.12PCh. 26 - Problem 26.13
Draw the products formed when each...Ch. 26 - Problem 26.14
What products are formed when ...Ch. 26 - Problem 26.15
Draw the product formed from...Ch. 26 -
What product is formed by ring-closing metathesis...Ch. 26 - Problem 26.17
What starting material is needed to...Ch. 26 - 26.18 In addition to organic halides, alkyl...Ch. 26 - 26.19 What product is formed by ring-closing...Ch. 26 - 26.20 Draw the products formed in each...Ch. 26 - What organic halide is needed to convert lithium...Ch. 26 - 26.22 How can you convert ethynylcyclohexane to...Ch. 26 - 26.23 What compound is needed to convert styrene...Ch. 26 - 26.24 What steps are needed to convert to octane...Ch. 26 - Prob. 26.25PCh. 26 - Prob. 26.26PCh. 26 - 26.27 Draw the products (including stereoisomers)...Ch. 26 - 26.28 Treatment of cyclohexene with and forms...Ch. 26 - Prob. 26.29PCh. 26 - 26.30 What starting material is needed to prepare...Ch. 26 - Prob. 26.31PCh. 26 - Prob. 26.32PCh. 26 - When certain cycloalkenes are used in metathesis...Ch. 26 - 26.34 Draw the products formed in each reaction.
...Ch. 26 - Prob. 26.35PCh. 26 - Draw a stepwise mechanism for the following...Ch. 26 - Sulfur ylides, like the phosphorus ylides of...Ch. 26 - Although diazomethane is often not a useful...Ch. 26 - Prob. 26.39PCh. 26 - Prob. 26.40PCh. 26 - Prob. 26.41PCh. 26 - Prob. 26.42PCh. 26 - 26.43 Devise a synthesis of each compound using a...Ch. 26 - 26.44 Devise a synthesis of each compound from...Ch. 26 - 26.45 Devise a synthesis of each compound from...Ch. 26 - 26.46 Devise a synthesis of each substituted...Ch. 26 - Biaryls, compounds containing two aromatic rings...Ch. 26 - Prob. 26.48PCh. 26 - 26.49 Draw the product formed from the...Ch. 26 - Prob. 26.50PCh. 26 - 26.51 Devise a synthesis of each of the following...Ch. 26 - Prob. 26.52PCh. 26 - 26.53 The following conversion, carried out in the...Ch. 26 - Prob. 26.54PCh. 26 - 26.55 Dimethyl cyclopropanes can be prepared by...Ch. 26 - Prob. 26.56P
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- Write 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_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_forwardCompounds 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_forward
- There 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_forwardCatalytic 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_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
- Compound 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_forwardReaction 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_forwarddraw structure of x and yarrow_forward
- The major product formed when methylenecyclohexane is treated with NBS in dichloromethane is 1-(bromomethyl)cyclohexene. Account for the formation of this product.arrow_forward#1077 of Paperchasel Compound A is treated with H₂SO4 to produce compound B which decolourises bromine in CCl4 Compound B is treated with cold, dilute KMnO4 to produce compound C. If compound A has the molecular formula C6H₁2O then: Select one: O a. B could be 1-hexene and C could be 1,2-hexanediol b. A could be cyclohexanol and B could be cyclohexane O c. A could be cyclohexanone and B could be cyclohexene O d. A could be cyclohexanol and C could be 1,2-cyclohexanediol e. B could be cyclohexene and C could be cyclohexanol #1444 of AromaticDirectors Which of the following are meta directing and deactivating substituents in aromatic electrophilic substitution reactions? 2) Br 3) OH 4) OR 5) NHCOR 1) CI Select one: 1), 2) and 3) O b. all of the above c. 1), 4) and 5) d. none of the above e. 3), 4), 5) and 6) a. 6) methylarrow_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?arrow_forward
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Chapter 4 Alkanes and Cycloalkanes Lesson 2; Author: Linda Hanson;https://www.youtube.com/watch?v=AL_CM_Btef4;License: Standard YouTube License, CC-BY
Chapter 4 Alkanes and Cycloalkanes Lesson 1; Author: Linda Hanson;https://www.youtube.com/watch?v=PPIa6EHJMJw;License: Standard Youtube License