EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 9781260475685
Author: SMITH
Publisher: MCGRAW-HILL HIGHER EDUCATION
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Chapter 9, Problem 75P
Interpretation Introduction
Interpretation: A stepwise mechanism for the dehydration of
Concept introduction: The dehydration of
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7. Draw the condensed structural formula of the product for each reaction. Name the reactant and the
product.
아
HS
OH
140°C
or th lall
180
Ho
CH CH3
CHy-CH -CH-CH + PE
CH3
What is the major organic product obtained from the following
reaction?
OH
OH
H,0
CH;CH,CH,CH,C=CH
OH
HgSO,
H,SO,
ÓH
O 1
O 2
O 3
O 4
Draw the alkene that can form the alcohol shown via an acid-catalyzed hydration reaction that does NOT require
a rearrangement.
Draw the starting alkene.
OH
H3O*
Chapter 9 Solutions
EBK ORGANIC CHEMISTRY
Ch. 9.1 - Problem 9.1 Label each ether and alcohol in...Ch. 9.3 - Give the IUPAC name for each compound.Ch. 9.3 - Problem 9.3 Give the structure corresponding to...Ch. 9.3 - Name each of the following ethers.Ch. 9.3 - Name each epoxide.
a. (two ways) b. c. (two...Ch. 9.6 - Problem 9.8 Draw the organic product of each...Ch. 9.6 - Prob. 9PCh. 9.6 - Problem 9.10 Draw the products of each reaction.
...Ch. 9.8 - Problem 9.11 Draw the products formed when each...Ch. 9.8 - Prob. 12P
Ch. 9.11 - Problem 9.18 Draw the products of each reaction,...Ch. 9.11 - Problem 9.19 What is the major product formed...Ch. 9.12 - Prob. 19PCh. 9.12 - Prob. 20PCh. 9.12 - Problem 9.22 Draw the organic products formed in...Ch. 9.12 - Problem 9.23 Draw two steps to convert into each...Ch. 9.13 - Prob. 23PCh. 9.13 - Problem 9.25 Draw the products of each reaction,...Ch. 9.13 - Draw the products formed when (S)-butan-2-ol is...Ch. 9.13 - Draw the product formed when (CH3)2CHOH is treated...Ch. 9.14 - What alkyl halides are formed when each ether is...Ch. 9.14 - Explain why the treatment of anisole with HBr...Ch. 9.15 - Name each thiol.
a. b.
Ch. 9.15 - Draw the product of each reaction. ac b.d.Ch. 9.15 - Give the IUPAC name for each sulfide.
a. b.
Ch. 9.15 - Draw the product of each reaction.
a. b.
Ch. 9.16 - Prob. 33PCh. 9.16 - The cis and trans isomers of 2, 3-dimethyloxirane...Ch. 9.16 - 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. 38PCh. 9 - 9.40 Give IUPAC name for each...Ch. 9 - Prob. 40PCh. 9 - Prob. 41PCh. 9 - 9.46 What alkenes are formed when each alcohol is...Ch. 9 - Prob. 46PCh. 9 - Prob. 51PCh. 9 - 9.57 Draw a stepwise, detailed mechanism for the...Ch. 9 - Prob. 53PCh. 9 - 9.59 Draw two different routes to each of the...Ch. 9 - Prob. 55PCh. 9 -
9.61 Draw the products formed when each ether is...Ch. 9 - 9.62 Draw a stepwise mechanism for each...Ch. 9 - Draw a stepwise, detailed mechanism for the...Ch. 9 - Prob. 59PCh. 9 - Draw the products of each reaction. a.c. b.d.Ch. 9 - Prob. 64PCh. 9 - Prob. 75P
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- Draw the product(s) formed by heating the compound shown in acidic methanol. CH;OH H* heatarrow_forwardWhat is the systematic name of the product P of this chemical reaction? 1 CH3-C-OH + NaOH P + H₂O X Śarrow_forwardAldehydes and ketones react with one molecule of an alcohol to form compounds called hemiacetals, in which there is one hydroxyl group and one ether-like group. Reaction of a hemiacetal with a second molecule of alcohol gives an acetal and a molecule of water. ROH, H+ OH OR Aldehyde/ketone Alcohol ROH, H+ Draw the structural formulas for the hemiacetal and the acetal formed between the following compounds: OH OH OR OR • Use the wedge/hash bond tools to indicate stereochemistry where it exists. + H₂Oarrow_forward
- Acid-catalyzed dehydration of secondary and tertiary alcohols proceeds through an E1 mechanism. The first step is the protonation of the alcohol oxygen to form an oxonium ion. Dehydration of 3-methyl-2-butanol forms one major and two minor organic products. Draw the structures, including hydrogen atoms, of the three organic products of this reaction. н н :бн н Нас. Нас. CHз CH3 ČH3 CH3 3-methyl-2-butanol an oxonium ion Major Product Minor Product Minor Productarrow_forwardדבקוו Draw the structure of the product formed in the reaction. 2 O H NaOH, ethanol heatarrow_forwardWhich one of these choices is the formula for an aldehyde? CH3CHO CH3OCH 3 CH3COCH 3 O CH3COOH O HC=CHarrow_forward
- Which of the following reagents converts an alcohol to an alkoxide? NaH HC1 Mg(OH)2 H₂SO4arrow_forwardCH,CH,CH,-OH Draw the structure of the product expected when each of the following alcohols is reacted with a sulfuric acid catalyst au the temperature indicated. H,SO, CH,-CH-CH, 180°C a. OH H,SO, CH, — CH—СH,—ОН 180°C b. CH; H,SO, CH-CH-OH 140°C с. CH, CH,-CH-CH,-CH, H,SO, d. 140°C d. OHarrow_forwardWhich of the following reagents converts an alcohol to an alkoxide? O NaH O HCI O H₂SO4 O Mg(OH)2arrow_forward
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