ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
10th Edition
ISBN: 9781260008562
Author: Carey
Publisher: MCG
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Chapter 7.15, Problem 23P
A study of the hydrolysis behavior of chlorofluorocarbons (CFCs) carried out by the U.S.Environmental Protection Agency found that
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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.)
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5. Acetone and 2-propanol are chemically interconvertible. Reduction (by the addition of the equivalent of H2) of acetone yields 2-propanol. Conversely, oxidation (by the removal of the equivalent of H2) of 2-propanol yields acetone.
Is the evaporation data for these substances the same or different? If different, can you account for why this may be the case from a comparison of the Lewis structures of each substance and the IMFs present in each substance? Explain.
Give one example for the hydration of Alkenes: that is: the addition of H2O by Hydroboration.
Chapter 7 Solutions
ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
Ch. 7.1 - Name each of the following using IUPAC...Ch. 7.1 - Prob. 2PCh. 7.2 - How many carbon atoms are sp2-hybridized in the...Ch. 7.3 - Prob. 4PCh. 7.3 - Are cis-2-hexene and trans-3-hexene stereoisomers?...Ch. 7.4 - Prob. 6PCh. 7.4 - Prob. 7PCh. 7.4 - Give the IUPAC name of each of the compounds in...Ch. 7.5 - Arrange the following in order of increasing...Ch. 7.6 - Prob. 10P
Ch. 7.6 - Standard enthalpies of formation are known for all...Ch. 7.6 - Prob. 12PCh. 7.6 - Despite numerous attempts, the alkene...Ch. 7.6 - Write structural formulas for the six isomeric...Ch. 7.7 - Place a double bond in the carbon skeleton shown...Ch. 7.9 - Identify the alkene obtained on dehydration of...Ch. 7.10 - Prob. 17PCh. 7.11 - Prob. 18PCh. 7.12 - Prob. 19PCh. 7.13 - The alkene mixture obtained on dehydration of...Ch. 7.14 - Write the structures of all the alkenes that can...Ch. 7.14 - Write structural formulas for all the alkenes that...Ch. 7.15 - A study of the hydrolysis behavior of...Ch. 7.15 - Use curved arrows to illustrate the electron flow...Ch. 7.15 - Predict the major product of the reaction shown.Ch. 7.16 - Prob. 26PCh. 7.17 - Prob. 27PCh. 7.18 - Prob. 28PCh. 7.19 - Predict the major organic product of each of the...Ch. 7.19 - A standard method for the synthesis of ethers is...Ch. 7 - Write structural formulas for each of the...Ch. 7 - Prob. 32PCh. 7 - Give an IUPAC name for each of the following...Ch. 7 - A hydrocarbon isolated from fish oil and from...Ch. 7 - Prob. 35PCh. 7 - Prob. 36PCh. 7 - Prob. 37PCh. 7 - Prob. 38PCh. 7 - Choose the more stable alkene in each of the...Ch. 7 - Suggest an explanation for the fact that...Ch. 7 - Prob. 41PCh. 7 - Write structural formulas for all the alkene...Ch. 7 - Prob. 43PCh. 7 - Prob. 44PCh. 7 - Predict the major organic product of each of the...Ch. 7 - Prob. 46PCh. 7 - Prob. 47PCh. 7 - The rate of the reaction In the first order in...Ch. 7 - Prob. 49PCh. 7 - Prob. 50PCh. 7 - You have available 2,2-dimethylcyclopentanol (A)...Ch. 7 - Prob. 52PCh. 7 - Prob. 53PCh. 7 - Prob. 54PCh. 7 - Acid-catalyzed dehydration of...Ch. 7 - The ratio of elimination to substitution is...Ch. 7 - Prob. 57PCh. 7 - Prob. 58DSPCh. 7 - Prob. 59DSPCh. 7 - Prob. 60DSPCh. 7 - Prob. 61DSPCh. 7 - A Mechanistic Preview of Addition Reactions The...Ch. 7 - Prob. 63DSPCh. 7 - Prob. 64DSPCh. 7 - Prob. 65DSP
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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.arrow_forwardWhat’s the role of NaBH4 in Oxymercuration-Demercuration of cyclohexene?arrow_forwardPrimary halogenoalkanes undergo hydrolysis by SN2 mechanism. State the meaning of S, N and 2 in SN2. Using curly arrows to show the movement of electrons give the reaction mechanism for the hydrolysis of 1-bromopropane [CH3CH2CH2Br] with aqueous hydroxide ions (OH-). The description should be detailed and must include the type of bond fission that takes place. You may sketch and insert suitable diagrams to aid your description if you wish.arrow_forward
- Give the product for the addition of chlorine when HCl reacts with 3-Hexyne in acetic acid (CH3COOH). Show the correct stereochemistry, (is the product Z or E isomer).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_forward4. Compound A has the formula C 8H 8. It reacts rapidly with KMnO 4 to give CO 2 and a carboxylic acid, B (C 7H 6O 2), but reacts with only 1 molar equivalent of H 2 on catalytic hydrogenation over a palladium catalyst. On hydrogenation under conditions that reduce aromatic rings, 4, equivalents of H 2 are taken up and hydrocarbon C (C 8H 16) is produced. What are the structures of A, B, and C.arrow_forward
- 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_forwardAn unknown hydrocarbon A with the formula C6H12 reacts with 1 molar equivalent of H2 over a palladium catalyst to give hydrocarbon B. Hydrocarbon A also reacts with OsO4 to give the glycol C. When oxidized with KMnO4 in acidic solution, A gives two fragments. One fragment is propanoic acid, CH3CH2COOH, and the other fragment is ketone D (R2C=O). What are the structures of A, B, C and D? Write all reactions.arrow_forwardNeed help with this Propose a preparation reaction for the formation of CH3NHCH2CH3 from organic compounds with only 1 or 2 carbonsarrow_forward
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