Introduction to General, Organic and Biochemistry
11th Edition
ISBN: 9781285869759
Author: Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher: Cengage Learning
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Chapter 11, Problem 11.56P
Interpretation Introduction
Interpretation:
Structural formula of isomer A, B and C to be identified which obtained on chlorination of C5 H12.
Concept Introduction:
Chlorination of an
Different isomer of same molecule may result in formation of different mono chlorinated product on chlorination.
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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.
1. There are five constitutional isomers with the molecular formula C6H14. When treated with chlorine at 300°C, isomer A gives a mixture of two monochlorination products. Under the same conditions, isomer B gives a mixture of five monochlorination products, isomer C gives four monochlorination products, and isomer D gives a mixture of three monochlorination products. From this information, draw the structure of isomer B.
2. Is it possible to prepare 1-chloro-2,2-dimethylpropane in high yield by halogenation of an alkane? _____no/yes
How many monohalo isomers are possible upon radical halogenation of the parent alkane? _____
(Consider stereoisomers as well.)
Please answer very soon will give rating surely
Both questions answers needed
Compound A (C6H14) forms three different monochlorides by photochemical chlorination. One of these monochlorides is inert to E2 elimination. The other two monochlorides produce the same alkene B (C6H12) when heated with potassium tert-butoxide in tert-butyl alcohol.Identify compound A, the three monochlorides, and alkene B.
Chapter 11 Solutions
Introduction to General, Organic and Biochemistry
Ch. 11.2 - Prob. 11.1PCh. 11.3 - Prob. 11.2PCh. 11.3 - Prob. 11.3PCh. 11.4 - Problem 11-4 Write the molecular formula and IUPAC...Ch. 11.6 - Problem 11-5 Write the molecular formula and IUPAC...Ch. 11.7 - Prob. 11.6PCh. 11.8 - Prob. 11.7PCh. 11.9 - Prob. 11.8PCh. 11.10 - Prob. 11.9PCh. 11 - Answer true or false. A hydrocarbon is composed...
Ch. 11 - 11-11 Define: Hydrocarbon Alkane Saturated...Ch. 11 - 11-12 Why is it not accurate to describe an...Ch. 11 - 11-13 What is meant by the term line-angle formula...Ch. 11 - Prob. 11.14PCh. 11 - Write the molecular formula for each alkane.Ch. 11 - Answer true or false. Constitutional isomers have...Ch. 11 - Which statements are true about constitutional...Ch. 11 - Prob. 11.18PCh. 11 - Each member of the following set of compounds is...Ch. 11 - Prob. 11.20PCh. 11 - 11-21 In the six following sets, which pairs of...Ch. 11 - Draw line-angle formulas for the nine...Ch. 11 - Answer true or false. The parent name of an alkane...Ch. 11 - Prob. 11.24PCh. 11 - Among the ingredients listed in one commercial...Ch. 11 - Prob. 11.26PCh. 11 - Answer true or false. Cycloalkanes are saturated...Ch. 11 - Prob. 11.28PCh. 11 - Prob. 11.29PCh. 11 - Prob. 11.30PCh. 11 - Prob. 11.31PCh. 11 - 11-32 Calculate the actual C-C-C bond angles in...Ch. 11 - Prob. 11.33PCh. 11 - 11-34 What structural feature of cycloalkanes...Ch. 11 - Prob. 11.35PCh. 11 - 11-36 Name and draw structural formulas for the...Ch. 11 - Name and draw structural formulas for the six...Ch. 11 - 11-38 Why is equatorial methylcyclohexane more...Ch. 11 - Prob. 11.39PCh. 11 - Consider a cyclohexane ring substituted with one...Ch. 11 - Prob. 11.41PCh. 11 - In Problem 11-22, you drew structural formulas for...Ch. 11 - Which unbranched alkane (Table 11-4) has about the...Ch. 11 - Prob. 11.44PCh. 11 - Prob. 11.45PCh. 11 - Prob. 11.46PCh. 11 - Prob. 11.47PCh. 11 - 11-48 How are the boiling points of hydrocarbons...Ch. 11 - Answer true or false. Combustion of alkanes is an...Ch. 11 - 11-50 Write balanced equations for the combustion...Ch. 11 - The heat of combustion of methane, a component of...Ch. 11 - 11-52 Draw structural formulas for these...Ch. 11 - Prob. 11.53PCh. 11 - 11-54 Complete and balance the equation for the...Ch. 11 - Name and draw structural formulas for all pos...Ch. 11 - Prob. 11.56PCh. 11 - Prob. 11.57PCh. 11 - 11-58 (Chemical Connections 11A) How many rings in...Ch. 11 - Prob. 11.59PCh. 11 - Prob. 11.60PCh. 11 - Prob. 11.61PCh. 11 - 11-62(Chemical Connections 11C) What are Freons?...Ch. 11 - 11-63 (Chemical Connections 11C) In what way do...Ch. 11 - (Chemical Connections 11C) What are HFCs and...Ch. 11 - Prob. 11.65PCh. 11 - Prob. 11.66PCh. 11 - Which of the following compounds can exist as...Ch. 11 - Prob. 11.68PCh. 11 - Dodecane, C12H26, is an unbranched alkane Predict...Ch. 11 - Prob. 11.70PCh. 11 - Prob. 11.71PCh. 11 - Prob. 11.72PCh. 11 - As stated in Section 11-9, the wax found in apple...Ch. 11 - Prob. 11.74P
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- An unknown hydrocarbon Q has a formula C6H12. Q reacts with osmium tetroxide to give a diol R when oxidized with KMnQ4 in an acidic medium Q gives two products. One product is propanoic acid and the other is ketone S. Provide reaction equations to identify the possible structures of Q, R and S.arrow_forwardCompounds 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?arrow_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_forward
- (a) Cyclohexa-1,3-diene can be converted into a tetrasubstituted haloalkane when reacted with bromine in ether. Write a balanced chemical equation for the reaction that occurs and state the expected observation. (b) Compound A and B are alkenes with the same molecular formula C5H10. Compound A is a branched-chain alkene while compound B is a straight-chain alkene. The reaction between compound A with hydrogen bromide produces major product C which is optically active. (i) Draw TWO (2) possible structures for compound B. (ii) Outline the mechanism for the reaction between compound A with hydrogen bromide to form major product C. (iii) Name the product formed when compound A undergoes bromination reaction.arrow_forwardWrite structural formulas for all aldehydes with the molecular formula C6H12O and give each its IUPAC name. Which of these aldehydes are chiralarrow_forwardGive the reaction equation for the alkene given to you assuming the reactant was Br2, in the presence ofwater indicating the stereochemistry of all products formed.arrow_forward
- Compound A (C5H8) readily reacts with bromine (Br2) at room temperature to discharge the purple colour of bromine and form Compound B (C5H8Br2). When Compound A is treated with H2 in the presence of a transition metal catalyst, it is converted to compound C (C5H10). When treated with HCl, compound A is converted to compound D (C5H9Cl). B, Cand D are saturated compounds. Given this information, propose structural formulas for compounds A, B, C, and D.arrow_forwardCompound A (C11H23Br) is a secondary alkyl halide. On being heated with a solution of sodium ethoxide in ethanol, compound A yielded a mixture of two alkenes B and C, each having molecular formula C11H22. Catalytic hydrogenation of the major isomer B or the minor isomer C gave only 3,5-diethylheptane. Draw structures for compounds A, B, and C consistent with these observations.arrow_forwardWhen bromine is added to two beakers, one containing phenyl isopropyl ether and the other containing cyclohexene, the bromine color in both beakers disappears. What observation could you make while performing this test that would allow you to distinguish the alkene from the aryl ether?arrow_forward
- Using 1-butene as the only organic starting material, outline how each of the following compounds might be synthesized from it, stating clearly the reaction conditions in each case. a. 2-butanol b. 2-butanone c. Butane d. 1,2-Dichlorobutanearrow_forwardA compound X of molecular formula C7H14 when hydrogenated produces 2,4-dimethylpentane and when hydroborated the obtained alcohol is 2,4-dimethyl-1-pentanol. a. What is the structure of X? b. If X is reacted with H2O catalyzed by H2SO4, what product is obtained? Write the structure, give the name, and write the complete mechanism, step by step of this reaction, in such a way as to explain the formation of the compound (DO NOT FORGET THE CORRECT USE OF ARROWS!).arrow_forwardThe reduction of a certain alkene gave 2-methylbutane. It also gave acetic acid (CH3CO2H) as one of the products when treated with hot basic KMnO4 followed by acidification. Give the IUPAC name of this alkene.arrow_forward
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