ORGANIC CHEMISTRY
6th Edition
ISBN: 9781266633973
Author: SMITH
Publisher: MCG
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Chapter 13.3, Problem 5P
Interpretation Introduction
Interpretation: The structures of A and B is to be determined.
Concept introduction: Halogens react with
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Compounds A and B are isomers having molecular formula C5H12. Heating A with Cl2 gives a single product of monohalogenation, whereas heating B under the same conditions forms three constitutional isomers. What are thestructures of A and B?
5) Compound A reacted with Mg in ether to give B. Compound B is with Ethyl bromide to give
Ethyl cyclohexane. What are the structures of A and B?
Compound L undergoes dehydrohalogenation to form hydrogen bromide and 1-methylcyclohexene.
What is dehydrohalogenation?
State the condition required for dehydrohalogenation.
Draw the structural formula of compound L and name L.
Chapter 13 Solutions
ORGANIC CHEMISTRY
Ch. 13.1 - Prob. 1PCh. 13.1 - Prob. 2PCh. 13.2 - Prob. 3PCh. 13.3 - Prob. 4PCh. 13.3 - Prob. 5PCh. 13.4 - Prob. 7PCh. 13.5 - Problem 15.8 Which bond in the each compound is...Ch. 13.6 - Prob. 9PCh. 13.6 - Prob. 10PCh. 13.7 - Prob. 11P
Ch. 13.7 - Prob. 12PCh. 13.8 - Prob. 13PCh. 13.8 - Prob. 14PCh. 13 - Prob. 27PCh. 13 - Prob. 28PCh. 13 - Prob. 34PCh. 13 - 15.37 What alkane is needed to make each alkyl...Ch. 13 - 15.38 Which alkyl halides can be prepared in good...Ch. 13 - Prob. 37PCh. 13 - 15.40 Explain why radical bromination of p-xylene...Ch. 13 - a. What product(s) (excluding stereoisomers) are...Ch. 13 - Prob. 40PCh. 13 - 15.43 Draw the products formed when each alkene is...Ch. 13 - 15.44 Draw all constitutional isomers formed when...Ch. 13 - 15.45 Draw the organic products formed in each...Ch. 13 - Prob. 45PCh. 13 - 15.47 Treatment of a hydrocarbon A (molecular...Ch. 13 - 15.48 Draw the products formed in each reaction...Ch. 13 - 15.53 Consider the following bromination: .
a....Ch. 13 - 15.54 Draw a stepwise mechanism for the following...Ch. 13 - Prob. 57PCh. 13 - 15.57 Devise a synthesis of each compound from...Ch. 13 - Prob. 59PCh. 13 - Prob. 60PCh. 13 - 15.60 Devise a synthesis of each compound using ...Ch. 13 - Prob. 62PCh. 13 - Prob. 63PCh. 13 - 15.63 As described in Section 9.16, the...Ch. 13 - 15.64 Ethers are oxidized with to form...
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- Compound W has molecular formula C₁4H18 and reacts with H₂ to form X. Oxidative cleavage of W with O3 followed by CH3 SCH3 affords Y. What is the structure of W?arrow_forwardCompound A (C3H,,Br) undergo dehydrohalogenation to produce major compound B. Compound C was formed when compound B undergo halogenation in room temperature. Compound B undergo halogenation in aqueous solution to form compound D. Compound B undergo hydrohalogenation in the presence of H,02 to form Compound E. Compound B undergo oxidation with hot acidified KMNO, to produce compound F and Compound G. Compound H was produced when Compound B react with cold KMN04. Compound B undergo ozonolysis to form Compound I and Compound J. Compound K was formed when compound B reacted with hydrogen in the presence of platinum. Compound A reacted with sodium hydroxide to form compound L. Compound M was produced when compound A reacted with ammonia in ethanol while compound N was formed when compound A reacted with sodium cyanide. Reaction X happened when compound K reacted with bromine in the presences of UV light. a) Identify the possible structural formulae for compound A to N. The number of carbon…arrow_forwardCompound A has molecular formula C5H12 and undergoes monochlorination to produce four different constitutional isomers. Draw the structure of compound A.arrow_forward
- There are three constitutional isomers with the molecular formula C5H12. When treated with chlorine at 300°C, isomer A gives a mixture of four monochlorination products. Under the same conditions, isomer B gives a mixture of three monochlorination products and isomer C gives only one monochlorination product. From this information, assign structural formulas to isomers A, B, and C.arrow_forwardAn organic compound A reacts with sodium metal and forms B. On heating with conc H2SO4, A gives diethyl ether. What are A and B?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
- Compound A (C6H12O2) reacts with water, acid, and heatto yield compound B (C5H10O2) and compound C (CH4O).Compound B is acidic. Deduce possible structures of compounds A, B, and Carrow_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_forwardCompound A (C3H17B1) undergo dehydrohalogenation to produce major compound B. Compound C was formed when compound B undergo halogenation in room temperature. Compound B undergo halogenation in aqueous solution to form compound D. Compound B undergo hydrohalogenation in the presence of H202 to form Compound E. Compound B undergo oxidation with hot acidified KMN04 to produce compound F and Compound G. Compound H was produced when Compound B react with cold KMN04. Compound B undergo ozonolysis to form Compound I and Compound J. Compound K was formed when compound B reacted with hydrogen in the presence of platinum. Compound A reacted with sodium hydroxide to form compound L. Compound M was produced when compound A reacted with ammonia in ethanol while compound N was formed when compound A reacted with sodium cyanide. Reaction X happened when compound K reacted with bromine in the presences of UV light. a) Identify the possible structural formulae for compound A to N. The number of carbon…arrow_forward
- Hydrocarbon X has the formula C6H12.X reacts with one molar equivalent of hydrogen in the presence of a palladium catalyst to form a product having 12 primary hydrogens.Treatment of X with ozone followed by zinc in aqueous acid gives a mixture two aldehydes.What is the structure of X?arrow_forwardA is a compound with molecular formula of C6H10, contains three methylene units. A react with one equivalent of H2 over Pd/C to yield B. A reacts with aqueous acid to form a single product, C. A also undergoes hydroboration/ oxidation to form product D. Ozonolysis of A followed by reaction of dimethylsulfide form E with molecular formula C6H10O2. A react with bromine in dichloromethane form F with molecular formula of C6H10Br2. Draw the reaction scheme for all the reaction mentioned above and suggest structure for A – F.arrow_forwardCompounds A and B are isomers of the molecular formula CyH19Br. Both yield the same alkene Cin an elimination reaction. Hydrogenation of C yields the product 2,3,3,4 tetramethyl pentane. What are the structures of A, B, and C?arrow_forward
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