ORGANIC CHEMISTRY
9th Edition
ISBN: 9780134645704
Author: WADE AND SIMEK
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 18, Problem 18.72SP
- a. Simple aminoacetals hydrolyze quickly and easily in dilute acid. Propose a mechanism for hydrolysis of the following aminoacetal:
- b. The nucleosides that make up DNA have heterocyclic rings linked to deoxyribose by an aminoacetal
functional group . Point out the amnioacetal linkages in deoxycytidine and deoxyadenosine.
- c. The stability of our genetic code depends on the stability of DNA. We are fortunate that the aminoacetal linkages of DNA are not easily cleaved. Show why your mechanism for part (a) does not work so well with deoxycytidine and deoxyadenosine.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Comparison of experimental data to “known” value. Monna and co-workers used radioactive isotopes to date sediments from lakes and estuaries.21 To verify this method they analyzed a 208Po standard known to have an activity of 77.5 decays/min, obtaining the following results.
77.09, 75.37, 72.42, 76.84, 77.84, 76.69, 78.03, 74.96, 77.54, 76.09, 81.12, 75.75
Do the results differ from the expected results at the 95% confidence interval?
Explain the difference between the propagated uncertainty and the standard deviation. Which number would you use to describe the uncertainty in the measurement? if the standard deviation is 0.01 and the propagated uncertainty is 0.03
Propagation of uncertainty. Find the absolute and percent relative uncertainty assuming the ±-values are random error.
7.65±0.04 + 5.28±0.02 – 1.12±0.01
85.6±0.9 × 50.2±0.7 ÷ 13.8±0.5
[4.88±0.07 + 3.22±0.05] / 1.53±0.02
Chapter 18 Solutions
ORGANIC CHEMISTRY
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
- Explain the difference between the propagated uncertainty and the standard deviation. Which number would you use to describe the uncertainty in the measurement?arrow_forwardCircle the compound in each pair where the indicated bond vibrates at higher frequency. WHY IS THIS? Provide thorough explanation to tie topic.arrow_forwardHow can you distinguish between each pair of compounds below using IR? Cite a bond and frequency that can be used to distinguish. Provide thorough steps and explanation.arrow_forward
- Propagation of uncertainty. Find the absolute and percent relative uncertainty assuming the ±-values are random error. 65±0.04 + 5.28±0.02 – 1.12±0.01 6±0.9 × 50.2±0.7 ÷ 13.8±0.5 [4.88±0.07 + 3.22±0.05] / 1.53±0.02arrow_forwardMatch to correct spectrum and explain the bonds and frequencies used to tell what spectrum connected to the given option. Thanks.arrow_forwardDraw the virtual orbitals for the planar and pyramidal forms of CH3 and for the linear and bent forms of CH2arrow_forward
- Q2: Draw the molecules based on the provided nomenclatures below: (2R,3S)-2-chloro-3-methylpentane: (2S, 2R)-2-hydroxyl-3,6-dimethylheptane:arrow_forwardQ3: Describes the relationship (identical, constitutional isomers, enantiomers or diastereomers) of each pair of compounds below. ག H CH3 OH OH CH3 H3C OH OH OH ////////// C CH3 CH3 CH3 CH3 H3C CH 3 C/III..... Physics & Astronomy www.physics.northweste COOH H нош..... H 2 OH HO CH3 HOOC H CH3 CH3 CH3 Br. H H Br and H H H Harrow_forwardQ1: For each molecule, assign each stereocenter as R or S. Circle the meso compounds. Label each compound as chiral or achiral. OH HO CI Br H CI CI Br CI CI Xf x f g Br D OH Br Br H₂N R. IN Ill I -N S OMe D II H CO₂H 1/111 DuckDuckGarrow_forward
- These are synthesis questions. You need to show how the starting material can be converted into the product(s) shown. You may use any reactions we have learned. Show all the reagents you need. Show each molecule synthesized along the way and be sure to pay attention to the regiochemistry and stereochemistry preferences for each reaction. If a racemic molecule is made along the way, you need to draw both enantiomers and label the mixture as "racemic". All of the carbon atoms of the products must come from the starting material! ? H Harrow_forwardQ5: Draw every stereoisomer for 1-bromo-2-chloro-1,2-difluorocyclopentane. Clearly show stereochemistry by drawing the wedge-and-dashed bonds. Describe the relationship between each pair of the stereoisomers you have drawn.arrow_forwardClassify each pair of molecules according to whether or not they can participate in hydrogen bonding with one another. Participate in hydrogen bonding CH3COCH3 and CH3COCH2CH3 H2O and (CH3CH2)2CO CH3COCH3 and CH₂ CHO Answer Bank Do not participate in hydrogen bonding CH3CH2OH and HCHO CH3COCH2CH3 and CH3OHarrow_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
Chemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Lipids - Fatty Acids, Triglycerides, Phospholipids, Terpenes, Waxes, Eicosanoids; Author: The Organic Chemistry Tutor;https://www.youtube.com/watch?v=7dmoH5dAvpY;License: Standard YouTube License, CC-BY