General, Organic, and Biological Chemistry - 4th edition
4th Edition
ISBN: 9781259883989
Author: by Janice Smith
Publisher: McGraw-Hill Education
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 12.9, Problem 12.21P
Interpretation Introduction
Interpretation:
Structures of the two alkyl chlorides produced from chlorination of normal butane must be drawn.
Concept introduction:
Butane has two types of hydrogen, primary and secondary. Thus, it will provide two different chlorinated products.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Reaction of butane (CH 3CH 2CH 2CH 3) with Cl 2 in the presence of light forms two different alkyl chlorides that have molecular formula C 4H 9Cl. Draw the structures of both alkyl chlorides.
An unknown hydrocarbon A with the formula C6H12 reacts with 1 molar equivalent of H2 over a palladium catalyst. Hydrocarbon A also reacts with OsO4 to give diol B. When oxidized with KMnO4 in acidic solution, A gives two fragments. One fragment is propanoic acid, CH3CH2CO2H, and the other fragment is ketone C. What are the structures of A, B, and C? Write all reactions, and show your reasoning.
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?
Chapter 12 Solutions
General, Organic, and Biological Chemistry - 4th edition
Ch. 12.1 - How many hydrogen atoms are present in each...Ch. 12.1 - Which formulas represent acyclic alkanes and which...Ch. 12.2 - Are the compounds in each pair constitutional...Ch. 12.2 - Draw two isomers with molecular formula C6H14 that...Ch. 12.2 - Prob. 12.3PCh. 12.2 - Classify the carbon atoms in each compound as 1°,...Ch. 12.2 - Prob. 12.4PCh. 12.2 - Prob. 12.5PCh. 12.2 - Prob. 12.6PCh. 12.2 - Prob. 12.7P
Ch. 12.2 - Prob. 12.8PCh. 12.2 - Prob. 12.9PCh. 12.4 - Give the IUPAC name for each compound.Ch. 12.4 - Prob. 12.10PCh. 12.4 - Give the IUPAC name for each compound....Ch. 12.4 - Prob. 12.5PPCh. 12.4 - Prob. 12.6PPCh. 12.4 - Prob. 12.12PCh. 12.5 - Prob. 12.13PCh. 12.5 - Prob. 12.14PCh. 12.5 - Give the IUPAC name for each compound.Ch. 12.5 - Prob. 12.15PCh. 12.7 - Answer the following questions about pentane...Ch. 12.7 - Prob. 12.17PCh. 12.7 - Prob. 12.18PCh. 12.8 - Prob. 12.19PCh. 12.9 - Prob. 12.20PCh. 12.9 - Prob. 12.21PCh. 12.9 - Prob. 12.22PCh. 12 - Prob. 23PCh. 12 - Prob. 24PCh. 12 - The waxy coating on the surface of apple skins...Ch. 12 - Prob. 26PCh. 12 - Classify each carbon as 1°, 2°, 3°, or 4°. a....Ch. 12 - Give the structure of an alkane that fits each...Ch. 12 - Prob. 29PCh. 12 - Label each pair of compounds as constitutional...Ch. 12 - Consider compounds A, B, and C. Label each pair of...Ch. 12 - Consider compounds D,E, and F. Label each pair of...Ch. 12 - Prob. 33PCh. 12 - Consider compounds A-E and label each pair of...Ch. 12 - Draw structures that fit the following...Ch. 12 - Draw the five constitutional isomers having...Ch. 12 - Prob. 37PCh. 12 - Prob. 38PCh. 12 - Draw the five constitutional isomers that have...Ch. 12 - Pristane is a high molecular weight alkane found...Ch. 12 - Give the IUPAC name for each of the five...Ch. 12 - Give the IUPAC name for each of the five cyclic...Ch. 12 - Give the IUPAC name for each compoundCh. 12 - Give the IUPAC name for each compound.Ch. 12 - Give the IUPAC name for each compound. c....Ch. 12 - Give the IUPAC name for each compound.Ch. 12 - Give the IUPAC name for each cycloalkane.Ch. 12 - Give the IUPAC name for each ccycloalkane.Ch. 12 - Prob. 49PCh. 12 - Give the structure corresponding to each IUPAC...Ch. 12 - Each of the following IUPAC names is incorrect....Ch. 12 - Each of the following IUPAC names is incorrect....Ch. 12 - Draw three constitutional isomers having molecular...Ch. 12 - Draw four constitutional isomers having molecular...Ch. 12 - Draw a skeletal structure for each compound octane...Ch. 12 - Convert each compound to a skeletal structure CH3(...Ch. 12 - Convert each skeletal structure to a complete...Ch. 12 - Convert each skeletal structure to a complete...Ch. 12 - Which compound in each pair has the higher melting...Ch. 12 - Which compound in each pair has the higher boiling...Ch. 12 - Branching in an alkane chain decreases surface...Ch. 12 - Explain why the boiling points of heptane [CH3( CH...Ch. 12 - Explain why hexane is more soluble in...Ch. 12 - Mineral oil and Vaseline are both mixtures of...Ch. 12 - Write a balanced equation for the combustion of...Ch. 12 - Write a balanced equation for the combustion of...Ch. 12 - Write a balanced equation for the incomplete...Ch. 12 - Prob. 68PCh. 12 - Prob. 69PCh. 12 - Prob. 70PCh. 12 - Prob. 71PCh. 12 - Prob. 72PCh. 12 - Prob. 73PCh. 12 - Prob. 74PCh. 12 - Prob. 75PCh. 12 - Prob. 76PCh. 12 - Prob. 77PCh. 12 - Prob. 78PCh. 12 - Prob. 79PCh. 12 - A major component of animal fat is tristearin, (a)...Ch. 12 - Answer the following questions about the alkane...Ch. 12 - Prob. 82PCh. 12 - Answer the questions in Problem 12.81 for the...Ch. 12 - Prob. 84PCh. 12 - Prob. 85CPCh. 12 - Draw the structure of the 12 constitutional...Ch. 12 - Cyclopentane has a higher boiling point than...Ch. 12 - Prob. 88CP
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
- Compounds X and Y have the formula C6H₁2. Both X and Y react with one molar equivalent of hydrogen in the presence of a palladium catalyst to form 2-methylpentane. The heat of hydrogenation of X is less than that of Y. X and Y react with HBr to form a mixture of the same bromoalkanes, and they both undergo hydroboration/oxidation to give a mixture of the same alcohols. What is the structure of Y? • In cases where there is more than one answer, just draw one. MAVI Sn [F ? ChemDoodlearrow_forwardCompounds X and Y have the formula C6H12. Both X and Y react with one molar equivalent of hydrogen in the presence of a palladium catalyst to form 2-methylpentane. The heat of hydrogenation of X is less than that of Y. X and Y react with HBr to form a mixture of the same bromoalkanes, and they both undergo hydroboration/oxidation to give a mixture of the same alcohols. What is the structure of Y? • In cases where there is more than one answer, just draw one. + ChemDoodlearrow_forward5B In the following reactions, mixtures of alkenes and ethyl ethers are formed. Draw their structures. Explain which is or are likely to be the main product(s) in each reaction. In case of formation of two isomers of alkenes, explain which is formed in greater proportion CH3 CH3 H3C-C H -Br CH3 EtOHarrow_forward
- 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.arrow_forwardOne mole of an unknown hydrocarbon, compound C, in the presence of a platinum catalyst, adds 98.9 L of hydrogen, measured at 744 mm Hg and 22 degrees C , to form a saturated alkane which contains one ring. When one mole of compound C is reacted with ozone, followed by reduction with (CH3)2S , four moles of only one product was formed, whose condensed molecular formula is CHO -CHO. Give the structure of compound C. Explain your reasoningarrow_forwardAlkenes can be converted to alcohols by reaction with mercuric acetate to form a β-hydroxyalkylmercury(II) acetate compound, a reaction called oxymercuration. Subsequent reduction with NaBH4 reduces the C–Hg bond to a C–H bond, forming the alkyl alcohol, a reaction called demercuration. Draw the structures of the Hg-containing compound(s) and the final alcohol product(s) formed in the following reaction sequence, omitting byproducts. If applicable, draw hydrogen at a chirality center and indicate stereochemistry via wedge-and-dash bonds.arrow_forward
- An 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_forwardAcetyl chloride, CH3COCl, reacts with the hydroxyl groupsof alcohols to form ester groups with the elimination ofHCl. When an unknown compound X with formulaC4H8O3 reacted with acetyl chloride, a new compound Ywith formula C8H12O5 was formed.(a) How many hydroxyl groups were there in X?(b) Assume that X is an aldehyde. Write a possible structure for X and a possible structure for Y consistent with your structure for X.arrow_forwardGiven the molecular formula C5H12O, give the structures (any form) and names of a primary, secondary, and tertiary alcohol, and an ether (ether can be named for EC).arrow_forward
- Compounds Y and Z both have the formula C₂H18. Both Y and Z react with one molar equivalent of hydrogen in the presence of a palladium catalyst to form 2-methyloctane. The heat of hydrogenation of Y is less than that of Z. Y and Z each undergo hydroboration/oxidation to give a primary alcohol (OH attached to a primary carbon). What is the structure of Y? • In cases where there is more than one answer, just draw one. 1998) 0▾ + n [F ChemDoodle aarrow_forward1. (a) Draw structures of the seven isomeric alkynes of formula C6H10 - (b) Give the IUPAC and derived name of each. (c) Indicate which ones will react with Ag' or Cu(NH3)2.arrow_forwardb) An alkyl halide W has the molecular formula CaH,Br. One of the isomers , X can rotate plane-polarised light . Another isomer, Y is a primary alkyl halide that reacts with ethanolic potassium hydroxide to form alkene, Z which can reacts with ozone and zinc followed by hydrolysis to yield propanone and methanal. Identify the compounds X. Y and Z.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Chemistry: The Molecular ScienceChemistryISBN:9781285199047Author:John W. Moore, Conrad L. StanitskiPublisher:Cengage Learning
Chemistry: Principles and PracticeChemistryISBN:9780534420123Author:Daniel L. Reger, Scott R. Goode, David W. Ball, Edward MercerPublisher:Cengage Learning
Chemistry: The Molecular Science
Chemistry
ISBN:9781285199047
Author:John W. Moore, Conrad L. Stanitski
Publisher:Cengage Learning
Chemistry: Principles and Practice
Chemistry
ISBN:9780534420123
Author:Daniel L. Reger, Scott R. Goode, David W. Ball, Edward Mercer
Publisher:Cengage Learning