ORGANIC CHEMISTRY-PACKAGE
5th Edition
ISBN: 9781259935121
Author: SMITH
Publisher: MCG
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Chapter 12, Problem 12.9P
Interpretation Introduction
Interpretation: Among the given pair of
Concept introduction: The addition of
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Which alkyne has the smaller heat of hydrogenation, HC ≡ CCH2CH2CH3 or CH3C ≡ CCH2CH3? Explain your choice.
a. What hydrocarbon with molecular formula C4H10 forms only two monochlorinated products? Both products are achiral.
b. What hydrocarbon with the same molecular formula as in part a forms three monochlorinated products? One is achiral and two are chiral.
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Chapter 12 Solutions
ORGANIC CHEMISTRY-PACKAGE
Ch. 12 - Prob. 12.1PCh. 12 - Problem 12.2 What alkane is formed when each...Ch. 12 - Prob. 12.3PCh. 12 - Prob. 12.4PCh. 12 - Prob. 12.5PCh. 12 - Prob. 12.6PCh. 12 - Compound Molecular formula before...Ch. 12 - Problem 12.8 Draw the products formed when...Ch. 12 - Prob. 12.9PCh. 12 - Prob. 12.10P
Ch. 12 - Problem 12.11 (a) Draw the structure of a compound...Ch. 12 - Prob. 12.12PCh. 12 - Prob. 12.13PCh. 12 - Problem 12.14 Draw the products of each...Ch. 12 - Prob. 12.15PCh. 12 - Problem 12.16 Draw all stereoisomers formed when...Ch. 12 - Prob. 12.17PCh. 12 - Problem 12.18 Draw the products formed when both...Ch. 12 - Problem 12.19 Draw the products formed when each...Ch. 12 - Prob. 12.20PCh. 12 - Prob. 12.21PCh. 12 - Problem 12.22 Draw the products formed when each...Ch. 12 - Prob. 12.23PCh. 12 - Problem 12.24 Draw the organic products in each of...Ch. 12 - Prob. 12.25PCh. 12 - Prob. 12.26PCh. 12 - Problem 12.27 Draw the products of each Sharpless...Ch. 12 - Prob. 12.28PCh. 12 - 12.29 Draw the products formed when A is treated...Ch. 12 - Prob. 12.30PCh. 12 - 12.31 Devise a synthesis of the following compound...Ch. 12 - Prob. 12.32PCh. 12 - Prob. 12.33PCh. 12 - Prob. 12.34PCh. 12 - Prob. 12.35PCh. 12 - Prob. 12.36PCh. 12 - 12.37 Stearidonic acid (C18H28O2) is an...Ch. 12 - Draw the organic products formed when cyclopentene...Ch. 12 - Draw the organic products formed when allylic...Ch. 12 - Draw the organic products formed in each reaction....Ch. 12 - Prob. 12.41PCh. 12 - Prob. 12.42PCh. 12 - Prob. 12.43PCh. 12 - What alkene is needed to synthesize each 1,2-diol...Ch. 12 - Prob. 12.45PCh. 12 - 12.46 (a)What product is formed in Step [1] of the...Ch. 12 - Draw the products formed after Steps 1 and 2 in...Ch. 12 - 12.48 Draw the products formed in each oxidative...Ch. 12 - What alkene or alkyne yields each set of products...Ch. 12 - Prob. 12.50PCh. 12 - Prob. 12.51PCh. 12 - Prob. 12.52PCh. 12 - Prob. 12.53PCh. 12 - 12.54 An unknown compound A of molecular formula ...Ch. 12 - 12.55 DHA is a fatty acid derived from fish oil...Ch. 12 - Prob. 12.56PCh. 12 - 12.57 Draw the product of each asymmetric...Ch. 12 - 12.58 Epoxidation of the following allylic alcohol...Ch. 12 - Prob. 12.59PCh. 12 - 12.60 Identify A in the following reaction...Ch. 12 - Prob. 12.61PCh. 12 - 12.62 It is sometimes necessary to isomerize a cis...Ch. 12 - 12.63 Devise a synthesis of each compound from...Ch. 12 - Prob. 12.64PCh. 12 - Prob. 12.65PCh. 12 - 12.66 Devise a synthesis of each compound from the...Ch. 12 - Prob. 12.67PCh. 12 - Prob. 12.68PCh. 12 - 12.69 Devise a synthesis of each compound from as...Ch. 12 - Prob. 12.70PCh. 12 - Prob. 12.71PCh. 12 - 12.72 Draw a stepwise mechanism for the following...Ch. 12 - Prob. 12.73PCh. 12 - Prob. 12.74PCh. 12 - 12.75 Sharpless epoxidation of allylic alcohol X...
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- The sex attractant of the female tiger moth is an alkane of molecular formula C 18H 38. Is this molecule an acyclic alkane or a cycloalkane?arrow_forwardThe heat of combustion of decahydronaphthalene(C10H18) is -6286 kJ/mol. The heat of combustion ofnaphthalene (C10H8) is -5157 kJ/mol. (In both casesCO2(g) and H2O(l) are the products.) Calculate the heat of hydrogenationand the resonance energy of naphthalene.arrow_forwardwhat is the smallest alkane, the smallest terminal alkene, and the smallest terminal alkyne that are liquids at room temperature, which is generally taken to be 20 °C to 25 °C?arrow_forward
- a. What alkane, with molecular formula C5H12, forms only one monochlorinated product when it is heated with Cl2? b. What alkane, with molecular formula C7H16, forms seven monochlorinated products (disregarding stereoisomers) when heated with Cl2?arrow_forwardWhat compound is CH3-CH(CH3)-CH2-CH2-CHO ?arrow_forwardCan someone help me estimate the percentage of ethylcyclohexane molecules that have their substituents in an axial orientation at room temperature? I know how to draw a ethylcyclohexane molecule but I don't know how to go about this problem.arrow_forward
- How many unsaturations are present in C7H12?arrow_forwardDraw the constitutional isomer formed when the attached alkenes are treated with each set of reagents: [1] H2O, H2SO4; or [2] BH3 followed by H2O2, −OH.arrow_forwardWhich of these bonds to carbon would you expect to be rela-tively reactive: C—H, C—C, C—I, C=O, C—Li? Explainarrow_forward
- Which is the most stable: 3,4-dimethyl-2-hexene, 2,3-dimethyl-2-hexene, or 4,5-dimethyl-2-hexene? a. Which compound has the largest heat of hydrogenation? b. Which compound has the smallest heat of hydrogenation?arrow_forwarda. Which is the most stable: 3,4-dimethyl-2-hexene, 2,3-dimethyl-2-hexene, or 4,5-dimethyl-2-hexene? b. Which compound has the largest heat of hydrogenation? c. Which compound has the smallest heat of hydrogenation?arrow_forwardWhat hydrocarbon with the molecular formula C4H10 forms three monochlorinated products? One is achiral and two are chiral.arrow_forward
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