PKG ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259963667
Author: SMITH
Publisher: MCG
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Chapter 10, Problem 10.61P
Interpretation Introduction
Interpretation: The mechanism for the formation of two constitutional isomers when
Concept introduction: The reaction of hydrogen halide with
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Draw the products formed when the following alkynes are treated with each set of reagents: [1] H2O, H2SO4, HgSO4; or [2] R2BH followed by H2O2, −OH.
Draw 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.
When 2-pentene is treated with Cl, in methanol, three products are formed. Account for
the formation of each product (you need not explain their relative percentages).
CI OCH3
H,CO CI
CI CI
Cle
CH;CHCHCH,CH, + CH;CHCHCH,CH3 + CH,CHČHCH,CH,
CH;OH
CH;CH=CHCH,CH,
50%
35%
15%
Chapter 10 Solutions
PKG ORGANIC CHEMISTRY
Ch. 10 - Prob. 10.1PCh. 10 - Problem 10.2 How many degrees of unsaturation are...Ch. 10 -
Problem 10.3 How many degrees of unsaturation...Ch. 10 - Give the IUPAC name for each alkene. abcdeCh. 10 - Give the IUPAC name for each polyfunctional...Ch. 10 - Problem 10.6 Label each C-C double bond as E or Z....Ch. 10 - Prob. 10.7PCh. 10 - Prob. 10.8PCh. 10 - Prob. 10.9PCh. 10 - Problem 10.10 Rank the following isomers in order...
Ch. 10 - Linolenic acidTable 10.2 and stearidonic acid are...Ch. 10 - Prob. 10.12PCh. 10 - Problem 10.13 What product is formed when each...Ch. 10 - Prob. 10.14PCh. 10 - Problem 10.15 Draw the products formed when each...Ch. 10 - Prob. 10.16PCh. 10 - Prob. 10.17PCh. 10 - Addition of HBr to which of the following alkenes...Ch. 10 - Problem 10.19 Draw the products, including...Ch. 10 - Prob. 10.20PCh. 10 - Problem 10.21 What two alkenes give rise to each...Ch. 10 - Prob. 10.22PCh. 10 - Problem 10.23 Draw the products of each reaction,...Ch. 10 - Problem 10.24 Draw all stereoisomers formed in...Ch. 10 - Prob. 10.25PCh. 10 - Problem 10.26 What alkylborane is formed from...Ch. 10 - Draw the products formed when each alkene is...Ch. 10 - What alkene can be used to prepare each alcohol as...Ch. 10 - Prob. 10.29PCh. 10 - Draw the products of each reaction using the two...Ch. 10 - Problem 10.31 Devise a synthesis of each compound...Ch. 10 - Give the IUPAC name for each compound. a.b.Ch. 10 - a Label the carbon-carbon double bond in A as E or...Ch. 10 - Prob. 10.34PCh. 10 - 10.35 Calculate the number of degrees of...Ch. 10 - Prob. 10.36PCh. 10 - Label the alkene in each drug as E or Z....Ch. 10 - Give the IUPAC name for each compound. a. c. e. b....Ch. 10 - Prob. 10.39PCh. 10 - 10.40 (a) Draw all possible stereoisomers of, and...Ch. 10 - Prob. 10.41PCh. 10 - 10.42 Now that you have learned how to name...Ch. 10 - Prob. 10.43PCh. 10 - Prob. 10.44PCh. 10 - Prob. 10.45PCh. 10 - Draw the products formed when (CH3)2C=CH2 is...Ch. 10 - What alkene can be used to prepare each alkyl...Ch. 10 - Prob. 10.48PCh. 10 - Draw the constitutional isomer formed in each...Ch. 10 - Prob. 10.50PCh. 10 - Draw all stereoisomers formed in each reaction. a....Ch. 10 - Draw the products of each reaction, including...Ch. 10 - Prob. 10.53PCh. 10 - Prob. 10.54PCh. 10 - Prob. 10.55PCh. 10 - 10.56 Draw a stepwise mechanism for the following...Ch. 10 - Prob. 10.57PCh. 10 - Draw a stepwise mechanism for the conversion of...Ch. 10 - Draw a stepwise mechanism that shows how all three...Ch. 10 - Less stable alkenes can be isomerized to more...Ch. 10 - Prob. 10.61PCh. 10 - Prob. 10.62PCh. 10 - Bromoetherification, the addition of the elements...Ch. 10 - Devise a synthesis of each product from the given...Ch. 10 - 10.65 Draw a synthesis of each compound from...Ch. 10 - 10.66 Explain why A is a stable compound but B is...Ch. 10 - Prob. 10.67PCh. 10 - Prob. 10.68PCh. 10 - 10.69 Lactones, cyclic esters such as compound A,...Ch. 10 - 10.70 Draw a stepwise mechanism for the following...Ch. 10 - 10.71 Like other electrophiles, carbocations add...Ch. 10 - 10.72 Draw a stepwise mechanism for the...
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- draw the two possible carbocations that can form when this alkene reacts with a strong acid (such as HBr or H3O+). of the two structures you drew, circle the more stable carbocationarrow_forwardAn alkene with the molecular formula C10H18 is treated with ozone and then with zinc and acetic acid. The only product isolated from these reactions is: What is the structure of the alkene?arrow_forwardOne compound that contributes to the “seashore smell” at beaches in Hawai‘i is dictyopterene D', a component of a brown edible seaweed called limu lipoa. Hydrogenation of dictyopterene D' with excess H2 in the presence of a Pd catalyst forms butylcycloheptane. Ozonolysis with O3 followed by (CH3)2S forms CH2(CHO)2, HCOCH2CH(CHO)2, and CH3CH2CHO. What are possible structures of dictyopterene D'?arrow_forward
- Name the alkene below. Use ONLY E/Z designators to indicate stereochemistry. H H H3C CH3 CH;CH2CH2 CH3arrow_forwardIdentify two alkenes that react with HBr to form 1-bromo-1-methylcyclohexane without undergoing a carbocation rearrangement.arrow_forwardPropose a synthesis for the systemic agricultural fungicide tridemorph from dodecanoic acid (lauric acid), propene, and a one-carbon building block. How many stereoisomers are possible for tridemorph? CH3 →CH3(CH2)10COOH + CH3CH=CH, H3C (CH2) 12CH3 Tridemorph Dodecanoic acid Propene (Lauric acid)arrow_forward
- what is the condensed formula of the products obtained from halogenation with Cl?arrow_forwardDraw a structural formula for the major organic product of the following reaction: CH3 CH3 ● CH3 CH3 AAVIL + Br₂ Show product stereochemistry IF the reactant alkene has both carbons of the double bond within a ring. • Do not show stereochemistry in other cases. ● If enantiomers are formed, just draw one. CH₂Cl₂ Sn [F ? ChemDoodleⓇarrow_forwardDraw the products of the three step reaction sequence shown below. Ignore inorganic byproducts. If the reaction results in a mixture of ortho and para isomers, draw only the para-product.arrow_forward
- The addition reaction of an acid (HBr) to an alkene (CH3CH=CH2) follows Markovnikov's rule and involves: A) initial attack by Br– B) initial attack by Br• C) isomerization of CH3CH2CH2Br D) formation of a primary carbocation. E) formation of a secondary carbonation. (F) Formation of allyl carbocationarrow_forwardWhen an unsymmetrical alkene such as propene is treated with N-bromosuccinimide in aqueous dimethyl sulfoxide, the major product has the bromine atom bonded to the less highly substituted carbon atom. Is this Markovnikov or non-Markovnikov orientation? Show its reaction mechanism. OH Brz, H,O CH;CH=CH, CH;CHCH,Br What products would you expect from oxymercuration-demercuration of 1-hexene? Show the reaction mechanism. 1.Hg(AOc), H,0 CH;CH,CH,CH,CH=CH; 2. NaBH, hex-1-enearrow_forwardWhat reagent/reagents is/are necessary to transform the starting molecule into the desired product? OH ? CH;CHCH,CH || CH3CHarrow_forward
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