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 18.62SP
Two structures for the sugar glucose are shown on page 914. Interconversion of the open-chain and cyclic hemiacetal forms is catalyzed by either acid or base.
- a. Propose a mechanism for the cyclization, assuming a trace of acid is present.
- b. The cyclic hemiacetal is more stable than the open-chain form, so very little of the open-chain form is present at equilibrium. Will an aqueous solution of glucose reduce. Tollens reagent and give a positive Tollens test? Explain.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
The reaction will produce which of the following results?
A. Decolorization of a brown solution
B. Production of a brown precipitate
C. Acidification of a solution
D. Production of fumes
What property is expected in the organic product in the reaction?
A.Solubility in alcohol is increased
B.Polarity of the compound is decreased
C.A cis-configuration is expected.
D. The electrophile becomes a nucleophile.
Which among the reactants is a reducing agent?
A.Alkene
B.MnO4, anion
C.Water
D. All of the Above
Which base would be best for promoting elimination over substitution?
a. H20
b. CH3O-
c.(CH3)3CO-
d. CN-
46. Which carbonyl group of the given compound is most reactive for nucleophilic addition reaction?
A. Carbonyl Group 1
B. Carbonyl Group 2
C.Carbonyl Group 3
D. All have equal reactivity
47. Which of the following does NOT give a brick red precipitate with Fehling solution?
A Acetone
B. Acetaldehyde
C. Formalin
D. D-glucose
48. Which of the following structures contains a hemiacetal group
CO
OH
H₂C
0
OCH,
A
OH
OCH
H₂C-C-CH₂
C C.H. CH
OCH
OCH,
b
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
- Draw the organic products in each of the following reactions.arrow_forward2. Each of 10 stereoisomeric sugar derivatives can be prepared via a multiple-step synthesis starting from either glucuronolactone 1D or its enantiomer 1L. (J. Org. Chem. 2012, 77, 7777-7792). 1L A. Draw the structure of 1L. 1D OH HO N OH HO OH sugar derivative B. How many stereoisomers of 1D are possible? C. Now consider the 10 stereoisomeric sugar derivatives. Draw the structures of the eight chiral products (as pairs of enantiomers) and the two achiral products (hint: meso).arrow_forwardWhich coupling reaction(s) will successfully form the indicated bond? Choose one or more: A. organocuprate reaction B. Suzuki coupling reaction C. Heck coupling reaction D. alkene metathesis reactionarrow_forward
- Paused Complete the following reactions. 1. +H₂O NaBH mild oxidation Complete the following reactions. 1. Base cat. H3CH2C CH₂CH + H3CH2C- C -CH2CH3 2. OCH3 H3C-C -CH2CH3 + H₂O OCH3 3. 4. CH3 NaBH4 H3CH2C C CH2CH3 + CH3CH2OH 5. mild oxidationarrow_forwardi. LIAIH4 i. deprotection J ii. dehydration .CO2Me CH2=CHCOCH3 protection ii. H30* K The synthesis of K from H involves a 3-steps reaction as shown above. Hydrolysis of H followed by heating produces compound L. Give IUPAC name for L. Write the reaction mechanism involved during the heating process that brought iii. to the formation of L.arrow_forwardI 13. For the following transformation how many H atoms were added or lost? ■ a. Lost one b. Lost two c. Added one 144 d. Added two OH a. Ester b. Carboxylic acid c. Alcohol d. Alkyne ■ c. localizes d. stabilizes - 14. What functional group is present in the following compound? ■ - ■ MÜNA ■ 15. Delocalization of charge over two or more atoms a. destabilizes b. delocalizes " ■ O HEI! ■ a molecule. ■arrow_forward
- Draw the structure of the ff. aldehydes and ketones. a. 3-chlorobutanal 6. 8,8-dibromo -4-cthylcyclo hexanone C. 2,4-dimetnylpontanone • Draw the structure of the ff. compounds. a. oyclobutanecarboxylic acid b. 3,8-dimcthylpontancdioic acid C. 4-aminopcntanoic acid d. 2-mothylcycloheranecarooxylic acid m- chlorobėnzoic acidarrow_forwardQUESTION 18 The transformation of I to II is best accomplished by treating I with: NH3 Cl NH2 II O A. KOH O B. NH3 OC. HCI O D.H2 0 QUESTION 19 Click Save and Submit to save and submit. Click Save All Answers to save all answers. nere to search Esc F1 F2 F3 F4 F5 F7 F8 F9 %23 & 1 3 7 8 CO 5arrow_forward62. What are the possible products in Claisen condensation reaction. A. Beta hydroxyl ketone and an alcohol B. Beta hydroxyl ketone and a ketone C. Beta keto ester and an alcohol D. Beta keto ester and a ketone For Nos. 63-70 Choose: A -if the indicated property/behavior in item I is greater than in item II B-if the indicated property/behavior in item I is less than in item II. C- if the indicated property/behavior is equal in item I and item II. D- if the indicated data is insufficient to make a comparison.arrow_forward
- What statements correctly describe organometallic compounds? A. They have an ionic bond because the bond is between a metal and a nonmetal B. They are transformed into hydrocarbons by reacting with CH3OH or CH3COOH C. They have a polar covalent bond which makes carbon a nucleophile and an electrophile D. They react with epoxides to give an alcohol after hydrolysis. E. They are prepared by reacting an arene, alkene or alkane with alkali metals or group II and some transition. F. All are prepared by direct reaction of the metal of interest with any organic halide.arrow_forwardInstructions: Give an acceptable name for eachester. A. CH, CH2)CO,CH, B. COCHỊCH, C. CH₂CH₂CH₂CH₂COOCH₂CH₂CH₂ Instructions: Give the structure corresponding to each name. a. propyl propanoate b. butyl acetate c. ethyl hexanoate d. methyl benzoate Instructions: Give an acceptable name for each amide A. CH₂CH₂CH₂CH₂ NH₂ Instructions: Draw the structure of each amide. A. N,N-dimethylacetamidearrow_forwardAmino acids such as glycine are the building blocks of large molecule.called proteins that give structure to muscle, tendon, hair, and nails.a.Explain why glycine does not actually exist in the form with all atoms uncharged, but actually exists as a salt called a zwitterion. b.What product is formed when glycine is treated with concentrated HCl? c. What product is formed when glycine is treated with NaOH?arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY
Enzymes - Effect of cofactors on enzyme; Author: Tutorials Point (India) Ltd;https://www.youtube.com/watch?v=AkAbIwxyUs4;License: Standard YouTube License, CC-BY
Enzyme Catalysis Part-I; Author: NPTEL-NOC IITM;https://www.youtube.com/watch?v=aZE740JWZuQ;License: Standard Youtube License