Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 22, Problem 44P
The following reaction sequence represents an elegant method of synthesis of 2-deoxy-D-ribose, IV, published by D. C. C. Smith in 1955:
(a) What are the structures of II and III?
(b) Propose a mechanism for the conversion of III to IV.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
A key step in the hydrolysis of acetamide in aqueous acid proceeds by nucleophilic addition of
* OH
(a) H3O* to CH3Ĉ NH2
(b) H2O to CH3ČNH2
+ OH
+OH
(c) H3O* to CH,ČNH2
(d) HO¯ to CH3CNH2
(a) Dichloroalkane 3 undergoes an SÃ1 reaction with H₂O to give either 4
or 5. Answer BOTH parts (i) and (ii)
CI
ga
3
H₂O
OH
CI
OR
OH
4
5
(i) Draw mechanisms for the SN1 reaction of compound 3 to form
each compound 4 and 5.
(ii) With reference to your mechanisms explain why 4 is the major
product of this reaction.
50501
(11)
A
OB
C
D
A solution of which of the following alkyl halides in methanol will be optically active
to begin but slowly lose most or all of its optical activity when heated?
H
H
Br
H3CBr
Br
(B)
(A)
T
Br
(C)
(D)
Chapter 22 Solutions
Organic Chemistry
Ch. 22 - Prob. 1PPCh. 22 - Prob. 2PPCh. 22 - Prob. 3PPCh. 22 - Prob. 4PPCh. 22 - Prob. 5PPCh. 22 - Prob. 6PPCh. 22 - Prob. 7PPCh. 22 - Prob. 8PPCh. 22 - Practice Problem 22.9 What products would you...Ch. 22 - Prob. 10PP
Ch. 22 - Prob. 11PPCh. 22 - Prob. 12PPCh. 22 - Prob. 13PPCh. 22 - Prob. 14PPCh. 22 - Prob. 15PPCh. 22 - Prob. 16PPCh. 22 - Prob. 17PPCh. 22 - Prob. 18PPCh. 22 - Prob. 19PPCh. 22 - Prob. 20PCh. 22 - Prob. 21PCh. 22 - Prob. 22PCh. 22 - Prob. 23PCh. 22 - Prob. 24PCh. 22 - Prob. 25PCh. 22 - Prob. 26PCh. 22 - Prob. 27PCh. 22 - Prob. 28PCh. 22 - Prob. 29PCh. 22 - Prob. 30PCh. 22 - Prob. 31PCh. 22 - Prob. 32PCh. 22 - Prob. 33PCh. 22 - Prob. 34PCh. 22 - Prob. 35PCh. 22 - Prob. 36PCh. 22 - Prob. 37PCh. 22 - Prob. 38PCh. 22 - Arbutin, a compound that can be isolated from the...Ch. 22 - Prob. 40PCh. 22 - Prob. 41PCh. 22 - Prob. 42PCh. 22 - Prob. 43PCh. 22 - 22.44 The following reaction sequence represents...Ch. 22 - 22.45
The NMR data for the two anomers...Ch. 22 - Shikimic acid is a key biosynthetic intermediate...
Additional Science Textbook Solutions
Find more solutions based on key concepts
Whether a triglyceride from olive oil or from beef fat has higher melting point should be explained with reason...
Chemistry: Matter and Change
The smell of an active ingredient in muscle ointment needs to be determined. The method by which nose can detec...
Living by Chemistry
3.1 The reaction between reactant A (blue spheres) and reactant B (red spheres) is shown in the
following diag...
Chemistry: The Central Science (13th Edition)
Calculate the lattice energy of CaCl2 using a Born-Haber cycle and data from Appendices F and L and Table 7.5. ...
Chemistry & Chemical Reactivity
When a solid mixture consisting of 10.500 g calcium hydroxide and 11.125 g ammonium chloride is strongly heated...
General Chemistry: Principles and Modern Applications (11th Edition)
Draw the mechanism for the reaction of cyclohexene with HCl.
Organic Chemistry
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
- 4. (a) Outline the steps in the following transformation with corresponding structures : H?ICH1or C6H100 -H* Tautomerism Adipic acid Oxydation C6H100arrow_forward(a) Beginning with 100% (R)-2-chlorobutane, upon reaction with NaOH in polar aprotic solvent, what is the major product? OH (b) OH (c) a racemic mixture of a and b (d) there is no reactionarrow_forwardThe formation of Br2 from NBS first involves the reaction of NBS with HBr to form an iminol intermediate and molecular bromine. The intermediate then undergoes acid-catalyzed tautomerism to form succinimide, the byproduct of the reaction. Propose a curved-arrow mechanism for the conversion of NBS into succinimide that also accounts for the formation of Br2.arrow_forward
- (a) Give reasons :(i) CH3—CHO is more reactive than CH3COCH3 towards HCN.(ii) 4-nitrobenzoic acid is more acidic than benzoic acid.(b) Describe the following :(i) Acetylation (ii) Cannizzaro reaction (iii) Cross aldol condensationarrow_forward(b) Describe the hazards of (i) trioxygen: (ii) hydroxide ion; (ii) hydrogen sulfide. (c) Explain why an aqueous solution of sodium sulfide has an odor of hydrogen sulfide. (d) (11) Reduction of H,CCHCHO with NABH4 gives a product different from that of catalytic hydrogenation (H2 /Ni). What are the products?arrow_forward(c) Answer ALL parts (i) to (v). (i) Draw the structure of the enolate ion 5 formed by deprotonation of the ester 4 by the base NaOEt. (ii) Suggest a mechanism for the formation of the enolate 5 and for its reaction with ethanol to produce the diastereoisomeric ester 6. (iii) For each diastereoisomer (4 and 6) draw the two chair conformations (4 chair diagrams in total). (iv) By referring to your chair diagrams, predict which diastereoisomer (4 or 6) will predominate when equilibrium has been reached. (v) What do you think the result would be if the reaction was instead performed using NaOMe in MeOH? NaOEt O H он OEt OEt Ме. Me Ме Ме. Me- Me 4. 9arrow_forward
- Following compounds are given to you:2-Bromopentane, 2-Bromo-2-methylbutane, 1-Bromopentane(i) Write the compound which is most reactive towards SN2 reaction.(ii) Write the compound which is optically active.(iii) Write the compound which is most reactive towards β – elimination reactionarrow_forwardDraw the organic products formed in each of the following reactions. (i). (ii) (iii) (iv) +:C=C-H + H₂O CH₂C=CCH₂CH3 HgSO4, H₂SO4 Na, NH3 2 equiv Br₂ (1) Sia₂BH.THF (2) H₂O₂ NaOHarrow_forward(a) Give the products expected when (+)@glyceraldehyde reacts with HCN.(b) What is the relationship between the products? How might they be separated?(arrow_forward
- (10pts) Compound A, C10H16, was found to be optically active. On catalytic reduction over a palladium catalyst, 2 equivalents of hydrogen were absorbed, yielding compound B, CioH2o. On ozonolysis of A, two fragments were obtained. One fragment was identified as acetic acid (CHCOOH). The other fragment, compound C, was an optically active carboxylic acid, C8H14O2. Write reactions, and draw the correct structures for A-C, explain your answer in detail.arrow_forwardWhich one of the following statements best describes the chemistry of ring A? E B OH он, A H Oleandrin is a toxic cardiac glycoside found in the poisonous plant, oleander (Nerium oleander L). It has a very long IUPAC name: acetic acid [(35,5R, 10S,13R,14S, 16S, 17'R)-14-hydroxy-3-[[(2R,4S,5S,65)-5-hydroxy-4-methoxy-6-methyl- 2-tetrahydropyranyl]oxy]-10,13-dimethyl-17-(5-oxo-2H-furan-3-y)-1,2,3,4,5,6,7,8,9,11,12,15,16,17- tetradecahydrocyclopenta[a]phenanthren-16-yl] ester Ring-A can act as a reducing sugar Ring-A can undergo mutarotation Ring-A is non-reducing O Ring-A is a furanosearrow_forwardA key step in the synthesis of a natural product is shown below. Answer sections (iv) and (v) related to this reaction. OH R CO₂Me + S S P CO₂Me Heat H H CO₂Me (iv) Give a curly arrow reaction mechanism for the formation of compound Q and suggest why the formation of the given diastereomer is favoured. (v) Compound P can be formed from S and R. Suggest the identity of S and state what type of reaction can be used to form P.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Coenzymes and cofactors; Author: CH15 SWAYAM Prabha IIT Madras;https://www.youtube.com/watch?v=bubY2Nm7hVM;License: Standard YouTube License, CC-BY
Aromaticity and Huckel's Rule; Author: Professor Dave Explains;https://www.youtube.com/watch?v=7-BguH4_WBQ;License: Standard Youtube License