Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 18, Problem 18.58SP
When LiAIH4 reduces 3-methylcyclopentanone, the product mixture contains 60% cis-3-methylcydopentanol and 40% trans-3-methylcyclopentanol. Use your models, and make three-dimensional drawings to explain this preference for the cis isomer.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Draw the principal organic product for the reaction of 2-bromohexane with lithium in diethyl ether, followed by formaldehyde in diethyl ether, and then followed
by dilute acid.
Click and drag to start drawing a
structure.
X
A
G
P
Describe how 1-ethylcyclohexanol can be prepared from cyclohexane. You can use any inorganic reagents, any solvents, and any organic reagents as long as they contain no more than two carbons.
3. Imitation vanilla extract contains vanillin and propylene glycol. Analysis via GC-MS shows a small
quantity of a racemic mixture of a vanillin-propylene glycol acetal. Draw the structure of this acetal
(considering stereochemistry) and briefly explain why it is racemic.
HO
H3CO
vanillin
H
HO
OH
propylene glycol
Chapter 18 Solutions
Organic Chemistry (9th Edition)
Ch. 18.3 - Give the IUPAC name and (if possible) a common...Ch. 18.5D - NMR spectra for two compounds are given here,...Ch. 18.5D - Why were no products from the McLafferty...Ch. 18.5D - Use equations to show the fragmentation leading to...Ch. 18.5E - Prob. 18.5PCh. 18.7D - Show how you would synthesize each compound from...Ch. 18.8 - Prob. 18.7PCh. 18.9 - Predict the products of the following reactions....Ch. 18.9 - Show how the following transformations may be...Ch. 18.10 - Prob. 18.10P
Ch. 18.11 - Show how you would accomplish the following...Ch. 18.11 - Prob. 18.12PCh. 18.12 - Propose mechanisms for a. the acid-catalyzed...Ch. 18.12 - Rank the following compounds in order of...Ch. 18.13 - Prob. 18.15PCh. 18.13 - Show how you would accomplish the following...Ch. 18.14 - Prob. 18.17PCh. 18.14 - Prob. 18.18PCh. 18.14 - Prob. 18.19PCh. 18.14 - Prob. 18.20PCh. 18.15 - 2,4-Dinitrophenylhydrazine is frequently used for...Ch. 18.15 - Prob. 18.22PCh. 18.15 - Prob. 18.23PCh. 18.16 - Prob. 18.24PCh. 18.16 - Prob. 18.25PCh. 18.16 - Show what alcohols and carbonyl compounds give the...Ch. 18.16 - In the mechanism for acetal hydrolysis shown, the...Ch. 18.16 - Prob. 18.28PCh. 18.17 - Show how you would accomplish the following...Ch. 18.18 - Prob. 18.30PCh. 18.18 - Prob. 18.31PCh. 18.18 - Prob. 18.32PCh. 18.18 - Show how Wittig reactions might be used to...Ch. 18.19 - Predict the major products of the following...Ch. 18.20C - Prob. 18.35PCh. 18.20C - Predict the major products of the following...Ch. 18 - Draw structures of the following derivatives. a....Ch. 18 - Prob. 18.38SPCh. 18 - Predict the major products of the following...Ch. 18 - Rank the following carbonyl compounds in order of...Ch. 18 - Acetals can serve as protecting groups for...Ch. 18 - Sketch the expected proton NMR spectrum of...Ch. 18 - A compound of formula C6H10O2 shows only two...Ch. 18 - The proton NMR spectrum of a compound of formula...Ch. 18 - The following compounds undergo McLafferty...Ch. 18 - An unknown compound gives a molecular ion of m/z...Ch. 18 - Show how you would accomplish the following...Ch. 18 - Prob. 18.48SPCh. 18 - Prob. 18.49SPCh. 18 - Propose mechanisms for the following reactions.Ch. 18 - Show how you would accomplish the following...Ch. 18 - Show how you would synthesize the following...Ch. 18 - Predict the products formed when cyclohexanone...Ch. 18 - Predict the products formed when...Ch. 18 - Show how you would synthesize octan-2-one from...Ch. 18 - Prob. 18.56SPCh. 18 - Both NaBH4 and NaBD4 are commercially available,...Ch. 18 - When LiAIH4 reduces 3-methylcyclopentanone, the...Ch. 18 - Prob. 18.59SPCh. 18 - Show how you would accomplish the following...Ch. 18 - There are three dioxane isomers 1,2-dioxane,...Ch. 18 - Two structures for the sugar glucose are shown on...Ch. 18 - Prob. 18.63SPCh. 18 - Prob. 18.64SPCh. 18 - Prob. 18.65SPCh. 18 - Prob. 18.66SPCh. 18 - Within each set of structures, indicate which will...Ch. 18 - Prob. 18.68SPCh. 18 - Prob. 18.69SPCh. 18 - Prob. 18.70SPCh. 18 - The UV spectrum of an unknown compound shows...Ch. 18 - a. Simple aminoacetals hydrolyze quickly and...Ch. 18 - The mass spectrum of unknown compound A shows a...Ch. 18 - Prob. 18.74SPCh. 18 - Prob. 18.75SPCh. 18 - Prob. 18.76SPCh. 18 - Prob. 18.77SP
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- From the table of available reagents select the one(s) you would use to convert:3-pentanol to 3-bromopentane:cyclopentanol to trans-2-methylcyclopentanol:Use the minimum number of steps; in no case are more than four steps necessary.List reagents by letter in the order that they are used; example: fa.arrow_forwardDraw the line-angle formula of the enol formed in the following alkyne hydration reaction and then draw the structural formula of the carbonyl compound with which this enol is in equilibrium. -C=CH 1. (sia)2BH 2. NaOH/H₂O₂ an enol carbonyl compound • You do not have to consider stereochemistry. • Draw both the enol and the carbonyl forms. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures using the sign from the drop-down menu. ChemDoodleⓇ <arrow_forwardChoose reagents to convert 2-cyclohexenone to the following compounds. Syntheses may require several steps. Use letters from the table to list reagents in the order used (first at the left). Reagents 1. Li(CH3)2Cu 2. H30* 1. Li(CeHs)2Cu 2. H30* 1. Li(CH2=CH)2Cu 2. H3O* a b. 1. NaBH, CH2l2 / Zn(Cu) / ether (CgHs)3P*-CH2 2. H,O* NH3 / KOH 1. CH3M9B / dry ether 2 H30* H2 over Pd/C H2NNH2 / KOH h HN(CH3)2 KMNO4 / H30* CH3 b) Submit Answer Try Another Verslon 1 item attempt remainingarrow_forward
- Which of the following aldehydes has the highest solubility in water? A) CH₃CH₂C(=O)H B) CH₃CH₂CH₂CH₂C(=O)H C) CH₃(CH₂)₅C(=O)H D) CH₃(CH₂)₁₀C(=O)H E) All of these have equal solubility.arrow_forwardA lab technician planned to synthesize 2-bromopentane using 2-pentanol, heat, and HBr. However, the labtechnician did not have HBr in the lab. What other reagent(s) can the technician use to synthesize 2-bromopentane using 2-pentanol as the starting material?arrow_forwardDraw the principal organic product for the reaction when 2-bromopropane is treated with lithium in diethyl ether, followed by copper(I) iodide and then 1-bromoethane. Click and drag to start drawing a structure. Xarrow_forward
- Convert 2-pentanol into 2,3-dibromopentane. Draw structures of the starting material (2-pentanol) and final product (2,3-dibromopentane), and show the two reactions needed for this synthesis. Include the structure of the intermediate compound, and the reagents and conditions for each reaction. Then explain why 1,2-dibromopentane would not be a significant product of this synthesis.arrow_forwardFrom the table of available reagents select the one(s) you would use to convert: 3-pentanol to 3-bromopentane. 3-pentanol to 3-methylpentane. Use the minimum number of steps; in no case are more than four steps necessary. List reagents by letter in the order that they are used; example: fa. Reagents available а. ВН3, ТHF; then H2O2, OH f. Н2, Pd b. Br2 g. Mg c. CH3MgBr; then H30+ h. NABH4; then H3O+ d. i. PB13 CrO3, H, SO4, H20 e. CH2=0; then H3O+ j. POC1 , pyridinearrow_forward8) Show how the following conversions might be accomplished, including all reagents and intermediates. Br Y. OHarrow_forward
- 4. Draw the organic products of the reactions of (R)-2-iodobutane with azide ion and methanol. Draw allstereoisomers expected to form. (R)-2-iodobutane Na*N3* CH3OHarrow_forwardGive the systematic (IUPAC) names for these molecules. Boononon cnolonongron. НаСНз CHОССH2СH2СНCHЗ CH3 phenyl propanoate |4-methyl pentane methanoat Incorrect. You mixed up the acyl and alkoxy portions of the molecule. Name the alkoxy part first, followed by the acyl part.arrow_forward5. Describe an efficient synthesis of 1-methyl-1-cyclohexanol from cyclohexanol. Show the structure of the reagents, reactants and products from each step. Cyclohexanol -------> -----> 1-methyl-1-cyclohexanolarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
IR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=_TmevMf-Zgs;License: Standard YouTube License, CC-BY