Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 9, Problem 9.36P
Interpretation Introduction
(a)
Interpretation:
The product formed by the reaction of cyclopentene with chloroform in the presence of potassium tert-butoxide is to be predicted.
Concept introduction:
Interpretation Introduction
(b)
Interpretation:
The products formed by the reaction of
Concept introduction:
Alkenes on reaction with alkyl halide in the presence of a strong base give derivative of cyclopropane. The
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a) When (Z)-3-methylhex-3-ene undergoes hydroboration–oxidation, two isomeric products are formed. Give their structures, and label each asymmetric carbon atom as (R) or (S). What is the relationship between these isomers?
Disiamylborane adds only once to alkynes by virtue of its two bulky secondary isoamylgroups. Disiamylborane is prepared by the reaction of BH3 # THF with an alkene.(a) Draw the structural formulas of the reagents and the products in the preparation ofdisiamylborane.(b) Explain why the reaction in part (a) goes only as far as the dialkylborane. Why isSia3B not formed?
Draw the organic product obtained on treatment of each of the following two alkenes with bromine: (a) trans-2-pentene and (b) 1-
methylcyclohexene. Having done this, draw the product of the reaction of these same alkenes with bromine in aqueous solution.
Chapter 9 Solutions
Organic Chemistry
Ch. 9 - Prob. 9.1PCh. 9 - Prob. 9.2PCh. 9 - Prob. 9.3PCh. 9 - Prob. 9.4PCh. 9 - Prob. 9.5PCh. 9 - Prob. 9.6PCh. 9 - Prob. 9.7PCh. 9 - Prob. 9.8PCh. 9 - Prob. 9.9PCh. 9 - Prob. 9.10P
Ch. 9 - Prob. 9.11PCh. 9 - Prob. 9.12PCh. 9 - Prob. 9.13PCh. 9 - Prob. 9.14PCh. 9 - Prob. 9.15PCh. 9 - Prob. 9.16PCh. 9 - Prob. 9.17PCh. 9 - Prob. 9.18PCh. 9 - Prob. 9.19PCh. 9 - Prob. 9.20PCh. 9 - Prob. 9.21PCh. 9 - Prob. 9.22PCh. 9 - Prob. 9.23PCh. 9 - Prob. 9.24PCh. 9 - Prob. 9.25PCh. 9 - Prob. 9.26PCh. 9 - Prob. 9.27PCh. 9 - Prob. 9.28PCh. 9 - Prob. 9.29PCh. 9 - Prob. 9.30PCh. 9 - Prob. 9.31PCh. 9 - Prob. 9.32PCh. 9 - Prob. 9.33PCh. 9 - Prob. 9.34PCh. 9 - Prob. 9.35PCh. 9 - Prob. 9.36PCh. 9 - Prob. 9.37PCh. 9 - Prob. 9.38PCh. 9 - Prob. 9.39PCh. 9 - Prob. 9.40PCh. 9 - Prob. 9.41PCh. 9 - Prob. 9.42PCh. 9 - Prob. 9.43PCh. 9 - Prob. 9.44APCh. 9 - Prob. 9.45APCh. 9 - Prob. 9.46APCh. 9 - Prob. 9.47APCh. 9 - Prob. 9.48APCh. 9 - Prob. 9.49APCh. 9 - Prob. 9.50APCh. 9 - Prob. 9.51APCh. 9 - Prob. 9.52APCh. 9 - Prob. 9.53APCh. 9 - Prob. 9.54APCh. 9 - Prob. 9.55APCh. 9 - Prob. 9.56APCh. 9 - Prob. 9.57APCh. 9 - Prob. 9.58APCh. 9 - Prob. 9.59APCh. 9 - Prob. 9.60APCh. 9 - Prob. 9.61APCh. 9 - Prob. 9.62APCh. 9 - Prob. 9.63APCh. 9 - Prob. 9.64APCh. 9 - Prob. 9.65APCh. 9 - Prob. 9.66APCh. 9 - Prob. 9.67APCh. 9 - Prob. 9.68APCh. 9 - Prob. 9.69APCh. 9 - Prob. 9.70APCh. 9 - Prob. 9.71APCh. 9 - Prob. 9.72APCh. 9 - Prob. 9.73APCh. 9 - Prob. 9.74APCh. 9 - Prob. 9.75APCh. 9 - Prob. 9.76APCh. 9 - Prob. 9.77APCh. 9 - Prob. 9.78APCh. 9 - Prob. 9.79APCh. 9 - Prob. 9.80APCh. 9 - Prob. 9.81APCh. 9 - Prob. 9.82APCh. 9 - Prob. 9.83APCh. 9 - Prob. 9.84APCh. 9 - Prob. 9.85APCh. 9 - Prob. 9.86APCh. 9 - Prob. 9.87AP
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- Arrange the alkenes in each set in order of increasing rate of reaction with HI and explain the basis for your ranking. Draw the structural formula of the major product formed in each case. (a) and (b) H3CH₂CHC=CH₂ and (H3C) 2C=CHCH3arrow_forwardThe reaction of 1-bromopropane and sodium hydroxide in ethanol occurs by an SN2mechanism. What happens to the rate of this reaction under the following conditions?(a) The concentration of NaOH is doubled.(b) The concentrations of both NaOH and 1-bromopropane are doubled.(c) The volume of the solution in which the reaction is carried out is doubled.arrow_forwardWrite the structure of the major organic product formed in the reaction of 1-pentene with each of the following: (a) Hydrogen chloride (b) Dilute sulfuric acid (c) Diborane in diglyme, followed by basic hydrogen peroxide (d) Bromine in carbon tetrachloride (e) Bromine in water (f) Peroxyacetic acid (g) Ozone (h) Product of part (g) treated with zinc and water (i) Product of part (g) treated with dimethyl sulfide (CH3)2Sarrow_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_forwardProvide the IUPAC name for each of the following compounds. Pay close attention to stereochemistry. (a) (b) -NH2 (c) OH ОН NH2 NH2 НО .CI Br. NH2 O,N"arrow_forwardUsing cyclohexane as your starting material, show how you would synthesize each of the following compounds. (Onceyou have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.)(a) bromocyclohexane (b) cyclohexene (c) ethoxycyclohexane(d) 3-bromocyclohex-1-ene (e) cyclohexa-1,3-diene (f) cyclohexanolarrow_forward
- 2. (a) Reaction of an alkene with ozone followed by an oxidative workup gives the product shown. What is the structure of alkene A? A (b) Compounds B and C both have the formula C10H16. Hydrogenation of either compound over Pt gives the same product, cis-1-isopropyl-4-methylcyclohexane. Ozonolysis with reductive workup fragments the two compounds differently, as shown below. What are the structures of C B and C? (CHCl3, chloroform, is the solvent.) B 1) 03, CHCI 3 2) (CH3)2S 1) 03, CHC13 2) (CH3)2S H O 1) 03 2) H₂O2, H₂O H3C- H O CH3 3. (a) Draw the structures of all enols that would spontaneously form this ketone, including stereoisomers. + + I HO₂C H + La CH3CH₂-C-CH(CH3)2 O= (b) Would alkyne hydration be a good preparative method for this compound? If so, give the reaction. If not, explain why.arrow_forwardDeduce the structure of each compound from the information given. All unknowns in this problem have molecularformula C8H12.(a) Upon catalytic hydrogenation, unknown W gives cyclooctane. Ozonolysis of W, followed by reduction with dimethylsulfide, gives octanedioic acid, HOOC¬(CH2)6¬COOH. Draw the structure of W.(b) Upon catalytic hydrogenation, unknown X gives cyclooctane. Ozonolysis of X, followed by reduction with dimethylsulfide, gives two equivalents of butanedial, O“CH¬CH2CH2¬CH“O. Draw the structure of X.(c) Upon catalytic hydrogenation, unknown Y gives cyclooctane. Ozonolysis of Y, followed by reduction with dimethylsulfide, gives a three-carbon dialdehyde and a five-carbon dialdehyde. Draw the structure of Y.arrow_forwardDeduce the structure of each compound from the information given. All unknowns in this problem have molecularformula C8H12.(a) Upon catalytic hydrogenation, unknown W gives cyclooctane. Ozonolysis of W, followed by reduction with dimethylsulfide, gives octanedioic acid, HOOC¬(CH2)6¬COOH. Draw the structure of W.(b) Upon catalytic hydrogenation, unknown X gives cyclooctane. Ozonolysis of X, followed by reduction with dimethylsulfide, gives two equivalents of butanedial, O“CH¬CH2CH2¬CH“O. Draw the structure of X.(c) Upon catalytic hydrogenation, unknown Y gives cyclooctane. Ozonolysis of Y, followed by reduction with dimethylsulfide, gives a three-carbon dialdehyde and a five-carbon dialdehyde. Draw the structure of Y.*(d) Upon catalytic hydrogenation, unknown Z gives cis-bicyclo[4.2.0]octane. Ozonolysis of Z, followed by reductionwith dimethyl sulfide, gives a cyclobutane with a three-carbon aldehyde (¬CH2¬CH2¬CHO) group on C1 and aone-carbon aldehyde (¬CHO) group on C2. Draw the…arrow_forward
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