Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 7.6, Problem 14P
Write structural formulas for the six isomeric
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4.15 Polycyclic Systems
Identify the relationship between the following compounds.
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Carbon–carbon bond dissociation enthalpies have been measured for many alkanes. Identify the alkane in each of the following pairs that has the lower carbon–carbon bond-dissociation enthalpy, and explain the reason for your choice. (a) Ethane or propane (b) Propane or 2-methylpropane (c) 2-Methylpropane or 2,2-dimethylpropane (d) Cyclobutane or cyclopentane
The heat of combustion of cis-1,2-dimethylcyclopropane is larger than that of the trans isomer. Which isomer is more stable? Use drawings to explain this difference instability.
Chapter 7 Solutions
Organic Chemistry - Standalone book
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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- When two six-membered rings share a C—C bond, this bicyclic system is called a decalin. There are two possible arrangements: trans-decalin having two hydrogen atoms at the ring fusion on opposite sides of the rings, and cis-decalin having the two hydrogens at the ring fusion on thesame side.a.Draw trans- and cis-decalin using the chair form for the cyclohexane rings. b.The trans isomer is more stable. Explain why.arrow_forwardName the following hydrocarbons: H;C CH3 (a) H,C=Ċ-Ċ=CH, H H (b) H;C-C=C-C=C-CH3 H H CH3 (c) H;C-C-CH,–CH3 CH3 CH, (d) H;C-C-CH3arrow_forwardWhich of the compounds below has the LOWEST heat of combustion? OA) OB) D)arrow_forward
- Show that the addition of each CH2 unit to an alcohol molecule changes the heat of combustion by: 2(C-H)+1(C-C)+1.5(O=O) – [2(C=O)+2(O-H)]arrow_forwardIdentify which of the following compounds is expected to have the larger heat of combustionarrow_forward3. The heat of hydrogenation for allene, H½C = C= CH2, to yield propane is – 295 kJ/mol, and the heat of hydrogenation for a typical monosubstituted alkene such as propene is -126 kJ/mol. Is allene more stable or less stable than you might expect for a diene ? Explain.arrow_forward
- Draw the structure of cis-1,2-dimethylcyclohexane. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • You do not have to explicitly draw H atoms. opy astearrow_forward4. The enthalpies, AH°, for the hydrogenation of three alkenes are shown below: Alkene A: -50 kcal/mole Alkene B: -60 kcal/mole Alkene C: -70 kcal/mole Which alkene is the least stable and why?arrow_forwardThe skeletal line formula for a branched alkene is shown below. (i) What is the molecular formula of this compound? (ii) How many carbon atoms are in the longest chain, ignoring the double bond? (iii) What is the longest chain incorporating both carbons of the double bond? (iv) How many substituents are on this chain? (v) Give the IUPAC name for this compound. [6]arrow_forward
- Rank the following compounds according to their heat of combustion.arrow_forwardThe dehydrogenation of butane to trans-but-2-ene has ∆H° = +116 kJ>mol (+27.6 kcal> mol) and ∆S° = +117 J>kelvin@mol (+28.0 cal>kelvin@mol).(a) Compute the value of ∆G° for dehydrogenation at room temperature (25 °C or 298 °K). Is dehydrogenation favored or disfavored?(b) Compute the value of ∆G for dehydrogenation at 1000 °C, assuming that ∆S and ∆H are constant. Is dehydrogenation favored or disfavored?arrow_forward(a) Draw all stereoisomers formed by monobromination of the cis and trans isomers of 1,2-dimethylcyclohexane drawn below. (b) How do the products formed from each reactant compare-identical compounds, stereoisomers, or constitutional isomers? cis-1,2-dimethylcyclohexane trans-(1R.2S)-dimethylcyclohexanearrow_forward
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