Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card
5th Edition
ISBN: 9781260170405
Author: SMITH
Publisher: MCG
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Chapter 12, Problem 12.49P
What
a. and c. and
b. and two equivalents of
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What Wittig reagent and carbonyl compound are needed to prepare each alkene? When two routes are possible, indicate which route, if any, is preferred.
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OCH3
a.
C.
OH
b.
d.
Epoxidation is typically achieved by treating an alkene with:
a. bromine
b. NBS
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O d. BH3, then NaOH
Chapter 12 Solutions
Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card
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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- Show two methods to synthesize each alkene: a one-step method using a Wittig reagent, and a two-step method that forms a carbon–carbon bond with an organometallic reagent in one of the steps.arrow_forward5. What reagents are needed to convert toluene (C,H,CH,) to each compound? a. C.H.COOH b. C.H₂CH₂Br c. p-bromotoluene d. o-nitrotoluene e. p-ethyltoluene f.arrow_forwardDevise a synthesis of each compound from cyclohexene as the starting material. More than one step is needed.arrow_forward
- 13arrow_forwardDevise a synthesis of each alkene using a Wittig reaction to form the double bond. You may use benzene and organic alcohols having four or fewer carbons as starting materials and any required reagents. a. CH,CH2CH2CH=CHCH3 b. GgH;CH=CHCH2CH¿CH3 c. (CHa2C=CHCH(CH)2arrow_forwardDraw the products formed when (CH3)2C=CH2 is treated with each reagent. a.HBr b. H2O, H2SO4 c. CH3CH2OH, H2SO4 d. Cl2 e.Br2, H2O f.NBS (aqueous DMSO) g.[1] BH3; [2] H2O2, HO−arrow_forward
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- 10. What products are formed when the following compound is treated with each reagent? If no reaction occurs, write NR. a. H₂/Pd b. K₂Cr2O7 c. Tollen's reagent d. 2 equiv. CH3OH, H+ e. 2 equiv. CH3CH₂OH, H+ f. Product of (e), then H₂O/H*arrow_forwardWhich alkene cannot be converted into an alkyl bromide with HBr, ROOR, hv, A? III IV A. B. C. D. E. All react Which synthetic route is best to give the major product shown below. ? x XA OH A. 1. BH3; 2. H₂O2, NaOH; 3. HBr; 4. CH3CO₂H B. 1. Br₂, 2. NaCCH; H₂, Lindlar's; 3. O3; 4. H₂O C. 1. NBS, hv, A; 2. H₂, Pd; 3. NaO₂CCH3 D. 1. NBS, hv, A; 2. NaCCH; 3. H₂2, Pd; 4. O3; 5. H₂O E. 1. NBS, hv, A; 2. H₂, Pd; 3. NaCCH; 4. 03; 5. H₂O Which synthetic route is best for the transformation shown below? OH ? OH A. 1. H₂SO4/heat; 2. HgOAC2, H₂O; 3. NaBH4 B. 1. HBr; 2. NaOH, DMSO C. 1. TsCl, pyr; 2. NaOH, DMSO D. 1. TsCl, pyr; 2. KOtBu; 3. BH3-THF; 4. H₂O2, NaOH E. 1. H₂SO4/heat; 2. BH3-THF; 3. H₂O2, NaOH =Barrow_forwardWhat products (including stereoisomers, if applicable) are formed from the reaction of 3-bromo-3-methylpentane: a. with HO-? b. with H2O?arrow_forward
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Chapter 4 Alkanes and Cycloalkanes Lesson 2; Author: Linda Hanson;https://www.youtube.com/watch?v=AL_CM_Btef4;License: Standard YouTube License, CC-BY
Chapter 4 Alkanes and Cycloalkanes Lesson 1; Author: Linda Hanson;https://www.youtube.com/watch?v=PPIa6EHJMJw;License: Standard Youtube License