ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 9, Problem 9.14P
What other alkene is also formed along with Y in Sample Problem 9.3? What
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Draw the alkene that would react with the reagent given to account for the product formed.
? + H₂O
H₂SO4
CH3
CH3 CHCCH3
OH 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.
Sn [F
ChemDoodle
Draw the alkene that would react with the reagent given to account for the product formed.
? + HCI
CH3
CH3CCH3
CI
• 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.
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ChemDoodle
What other alkene is also formed along with Y in Sample Problem 9.3? What alkenes would form from X if no carbocation rearrangement occurred?
Chapter 9 Solutions
ORGANIC CHEMISTRY
Ch. 9 - Problem 9.1 Label each ether and alcohol in...Ch. 9 - Give the IUPAC name for each compound.Ch. 9 - Problem 9.3 Give the structure corresponding to...Ch. 9 - Name each of the following ethers.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 - Problem 9.8 Draw the organic product of each...Ch. 9 - Prob. 9.9PCh. 9 - Problem 9.10 Draw the products of each reaction.
...
Ch. 9 - Problem 9.11 Draw the products formed when each...Ch. 9 - Prob. 9.12PCh. 9 - Problem 9.13 Draw the structure of each...Ch. 9 - What other alkene is also formed along with Y in...Ch. 9 - Prob. 9.15PCh. 9 - Explain why two substitution products are formed...Ch. 9 - Draw the products of each reaction. a. b. c.Ch. 9 - Problem 9.18 Draw the products of each reaction,...Ch. 9 - Problem 9.19 What is the major product formed...Ch. 9 - Prob. 9.20PCh. 9 - Prob. 9.21PCh. 9 - Problem 9.22 Draw the organic products formed in...Ch. 9 - Problem 9.23 Draw two steps to convert into each...Ch. 9 - Prob. 9.24PCh. 9 - Problem 9.25 Draw the products of each reaction,...Ch. 9 - Draw the products formed when (S)-butan-2-ol is...Ch. 9 - Draw the product formed when (CH3)2CHOH is treated...Ch. 9 - What alkyl halides are formed when each ether is...Ch. 9 - Explain why the treatment of anisole with HBr...Ch. 9 - Name each thiol.
a. b.
Ch. 9 - Draw the product of each reaction. ac b.d.Ch. 9 - Give the IUPAC name for each sulfide.
a. b.
Ch. 9 - Draw the product of each reaction.
a. b.
Ch. 9 - Prob. 9.34PCh. 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. 9.39PCh. 9 - 9.40 Give IUPAC name for each...Ch. 9 - Prob. 9.41PCh. 9 - Prob. 9.42PCh. 9 - Prob. 9.43PCh. 9 - 9.44 Why is the boiling point of higher than...Ch. 9 - 9.45 Draw the organic product(s) formed when is...Ch. 9 - 9.46 What alkenes are formed when each alcohol is...Ch. 9 - Prob. 9.47PCh. 9 - 9.48 Draw the products of each reaction and...Ch. 9 - 9.49 Draw the product of the following reaction,...Ch. 9 - Prob. 9.50PCh. 9 - Prob. 9.51PCh. 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. 9.54PCh. 9 - Prob. 9.55PCh. 9 - Prob. 9.56PCh. 9 - 9.57 Draw a stepwise, detailed mechanism for the...Ch. 9 - Prob. 9.58PCh. 9 - 9.59 Draw two different routes to each of the...Ch. 9 - Prob. 9.60PCh. 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. 9.64PCh. 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. 9.67PCh. 9 - Prob. 9.68PCh. 9 - Prob. 9.69PCh. 9 - Prob. 9.70PCh. 9 - Prepare each compound from cyclopentanol. More...Ch. 9 - 9.72 Identify the reagents (a–h) needed to carry...Ch. 9 - Prob. 9.73PCh. 9 - 9.74 Treatment of with affords compound A and ....Ch. 9 - Prob. 9.75PCh. 9 - Prob. 9.76PCh. 9 - 9.77 Draw a stepwise, detailed mechanism for the...Ch. 9 - 9.78 Dehydration of with affords
as a minor...Ch. 9 - Prob. 9.79PCh. 9 - 9.80 Draw a stepwise mechanism for the following...Ch. 9 -
9.81 Aziridines are heterocycles that contain an...
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- Draw the structure for an alkene that gives the following reaction product. CH3 HCI CH3CHCH2CHCH3 CI • Ignore alkene stereochemistry. •You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. P. opy aste ChemDoodle"arrow_forwardDraw the alkene that would react with the reagent given to account for the product formed. ? + + H₂O **** H₂S04 • 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. CH3 CH3 CHCCH3 | | OH CH3 +1arrow_forward2. Explain the selectivity of the following reaction, which produces a single product despite both alkene carbons being equally substituted. H3C CF3 HBr CF3 H3C CF3 H3C Br- H3C only product -H CF3arrow_forward
- Draw the alkene that would react with the reagent given to account for the product formed. ? + H₂O H₂SO4 CH3 CH3CCH3 OH 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. Sn [F ChemDoodleⓇarrow_forwardPredict the oxidation product of treating the given alkene with a peroxyacid reagent. Omit byproducts. Draw the oxidation product. H. Harrow_forwardBased on the stability of alkenes, and the stability of any intermediates, which alkene do you think should be the predominate product? (There may be more than one...) OH conc. H₂SOarrow_forward
- Rank the following alkenes from least to most stable. Then explain why you picked this order.arrow_forwardBased on the hydrogenation reaction information, how many different alkene structures can you draw that could be Compound X? (If enantiomers are possible, count each pair of enantiomers as one structure.)arrow_forwardRank the alkenes shown from least exothermic (1) to most exothermic (4) heat of hydrogenation. a. b. C. d.arrow_forward
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