Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 9, Problem 9.28P
Draw the products formed when
relationshipbetween the starting alcohol and the final product?
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Students have asked these similar questions
Alkenes can be converted to alcohols by reaction with mercuric acetate to form a ß-hydroxyalkylmercury(II) acetate compound,
a reaction called oxymercuration. Subsequent reduction with NaBH reduces the C-Hg bond to a C-H bond, forming the alkyl
alcohol, a reaction called demercuration. Draw the structure of the Hg-containing compound and the final alcohol product
formed in the reaction sequence.
CH3
Hg(OOCCH3)2
NaBH4
HO™
Oxymercuration
product
Demercuration
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H₂O, THF
Draw the alcohol product of demercuration.
Draw the neutral product of oxymercuration.
Omit byproducts.
OH
Hg
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When 3-bromo-2,4-dimethylpentane is treated with sodium hydroxide, only one alkene is formed. Draw the product.
Determine the products formed when butanal (CH3CH₂CH₂CHO) is treated with each reagent.
OH
H₂00,C
H
CÓ CHI
DOCH,
COCH
CHO
OH
L
OH
CHO
OH
H
CH, CO, C
NaOCH, CH₂OH
HO
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NaBH
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Chapter 9 Solutions
Organic Chemistry-Package(Custom)
Ch. 9 - Draw all constitutional isomers having molecular...Ch. 9 - Prob. 9.2PCh. 9 - Give the IUPAC name for each compound.Ch. 9 - Problem 9.3 Give the structure corresponding to...Ch. 9 - Prob. 9.5PCh. 9 - Name CH33COCH3, a gasoline additive commonly...Ch. 9 - Name each epoxide.
a. (two ways) b. c. (two...Ch. 9 - Problem 9.6 Rank the following compounds in order...Ch. 9 - Which mechanism is favored by the use of crown...Ch. 9 - Draw the organic product of each reaction.
Ch. 9 - Prob. 9.11PCh. 9 - Prob. 9.12PCh. 9 - Prob. 9.13PCh. 9 - Prob. 9.14PCh. 9 - Problem 9.13 Draw the structure of each...Ch. 9 - What other alkene is also formed along with Y in...Ch. 9 - Prob. 9.17PCh. 9 - Explain how the reaction of CH32CHCHCl CH3 with...Ch. 9 - Prob. 9.19PCh. 9 - Draw the products of each reaction, indicating the...Ch. 9 - Problem 9.19 What is the major product formed...Ch. 9 - Prob. 9.22PCh. 9 - Prob. 9.23PCh. 9 - Problem 9.22 Draw the organic products formed in...Ch. 9 - Problem 9.23 Draw two steps to convert into each...Ch. 9 - Draw the products of each reaction, and indicate...Ch. 9 - Draw the products of each reaction, and include...Ch. 9 - Draw the products formed when (S)-butan-2-ol is...Ch. 9 - Prob. 9.29PCh. 9 - Prob. 9.30PCh. 9 - Explain why the treatment of anisole with HBr...Ch. 9 - Prob. 9.32PCh. 9 - The cis and trans isomers of 2, 3-dimethyloxirane...Ch. 9 - Problem 9.36 Draw the product of each...Ch. 9 - 9.37 Name each compound depicted in the...Ch. 9 - Answer each question using the ball-and-stick...Ch. 9 - Prob. 9.37PCh. 9 - a. Draw the structure of 1, 2, and 3 alcohol with...Ch. 9 - Give IUPAC name for each alcohol. a....Ch. 9 - Name each ether and epoxide. a.b.c.d.Ch. 9 - Prob. 9.41PCh. 9 - Draw the eight constitutional isomers with...Ch. 9 - Rank each group of compounds in order of: a....Ch. 9 - Prob. 9.44PCh. 9 - 9.44 Why is the boiling point of higher than...Ch. 9 - Draw the organic products formed when CH3CH2CH2OH...Ch. 9 - Draw the organic products formed when 1-methyl...Ch. 9 - What alkenes are formed when each alcohol is...Ch. 9 - Prob. 9.49PCh. 9 - Prob. 9.50PCh. 9 - 9.48 Draw the products of each reaction and...Ch. 9 - Prob. 9.52PCh. 9 - 9.52 Draw a stepwise mechanism for the following...Ch. 9 - 9.53 Although alcohol V gives a single alkene W...Ch. 9 - Prob. 9.55PCh. 9 - Prob. 9.56PCh. 9 - Prob. 9.57PCh. 9 - When CH3CH2CH2CH2OH is treated with H2SO4 NaBr,...Ch. 9 - 9.57 Draw a stepwise, detailed mechanism for the...Ch. 9 - Prob. 9.60PCh. 9 - Draw two different routes to each of the following...Ch. 9 - Prob. 9.62PCh. 9 - Prob. 9.63PCh. 9 - 9.62 Draw a stepwise mechanism for each...Ch. 9 - Draw a stepwise, detailed mechanism for the...Ch. 9 - Prob. 9.66PCh. 9 - Draw the products of each reaction. a.c. b.d.Ch. 9 - When each halohydrin is treated with, a product of...Ch. 9 - Prob. 9.69PCh. 9 - Devise a stepwise mechanism for the following...Ch. 9 - Draw the products of each reaction, and indicate...Ch. 9 - Prepare each compound from CH3CH2CH2CH2OH. More...Ch. 9 - Prepare each compound from cyclopentanol. More...Ch. 9 - 9.72 Identify the reagents (a–h) needed to carry...Ch. 9 - Prob. 9.75PCh. 9 - 9.74 Treatment of with affords compound A and ....Ch. 9 - Prob. 9.77PCh. 9 - Prob. 9.78PCh. 9 - 9.77 Draw a stepwise, detailed mechanism for the...Ch. 9 - Dehydration of 1, 2, 2-trimethylcyclohexanol with...Ch. 9 - Prob. 9.81PCh. 9 - 9.80 Draw a stepwise mechanism for the following...Ch. 9 -
9.81 Aziridines are heterocycles that contain an...
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- Two diastereomeric sets of enantiomers, A/B and C/D, exist for 3-bromo-2-butanol. When enantiomer A or B is treated with HBr, only racemic 2,3-dibromobutane is formed; no meso isomer is formed. When enantiomer C or D is treated with HBr, only meso 2,3-dibromobutane is formed; no racemic 2,3-dibromobutane is formed. Account for these observations.arrow_forwardGive the IUPAC name for the following compound. Be sure to indicate stereochemistry where necessary.arrow_forwardDraw the products formed when ethylene oxide is treated with following reagent. [1] HC=C−; [2] H2Oarrow_forward
- Convert propan-2-ol [(CH3)2CHOH] into each compound. You may use any other organic or inorganic compoundsarrow_forwardWhich alcohol is the most soluble in water? A CH;CH,CHOHCH3 B CH;CH2CH2CH2OH (c) (CH3)2CHCH2OH D (CH3)3COHarrow_forwardA 2-bromobutane react with methanol and form a enantiomeric pair of 2-methoxybutane. Draw the structures of the enntiomeric pairs of ethers.arrow_forward
- Draw a structural formula for the alkene you would use to prepare the alcohol shown by hydroboration/oxidation. CH3 HO CH3 •You do not have to consider stereochemistry. •You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. H3C-CH3 n [ ?arrow_forwardDraw the products formed when alkene reacts with these reagents: (i) H2 in the presence of Pd catalyst, (ii) HCl.arrow_forwardDraw the products formed when phenol (C6H5OH) is treated with following set of reagents. [1] CH3CH2Cl, AlCl3; [2] Br2, hνarrow_forward
- Dehydration of 1,2,2-trimethylcyclohexanol with H2SO4 affords 1-tert-butylcyclopentene as a minor product. (a) Draw a stepwise mechanism that shows how this alkene is formed. (b) Draw other alkenes formed in this dehydration. At least one must contain a five-membered ring.arrow_forwarddraw 2-cyclohexene-1-olarrow_forwardDraw a structural formula for the major product of the reaction shown. -CH₂CH3 Br₂ H₂O • 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 the reaction produces a racemic mixture, just draw one stereoisomer.arrow_forward
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