![ORGANIC CHEMISTRY](https://www.bartleby.com/isbn_cover_images/9781259977596/9781259977596_largeCoverImage.gif)
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
expand_more
expand_more
format_list_bulleted
Question
Chapter 21, Problem 21.82P
Interpretation Introduction
(a)
Interpretation: The structure of brevicomin is to be drawn.
Concept introduction: The acid-catalyzed cyclization of
Interpretation Introduction
(b)
Interpretation: The synthesis of
Concept introduction: The nucleophilic addition reactions are the common reactions, which form products like imines,
Expert Solution & Answer
![Check Mark](/static/check-mark.png)
Want to see the full answer?
Check out a sample textbook solution![Blurred answer](/static/blurred-answer.jpg)
Students have asked these similar questions
Brevicomin, the aggregation pheromone of the western pine bark beetle, contains a bicyclic bridged ring system and is prepared by the acidcatalyzed cyclization of 6,7-dihydroxy-nonan-2-one. a. Suggest a structure for brevicomin. b. Devise a synthesis of 6,7-dihydroxynonan-2-one from 6-bromohexan-2- one. You may also use three-carbon alcohols and any required organic or inorganic reagents.
Brevicomin, the aggregation pheromone of the western pine bark beetle, contains a bicyclic bridged ring system and is prepared by the acid-catalyzed cyclization of 6,7-dihydroxynonan- 2-one.
a. Suggest a structure for brevicomin.
b. Devise a synthesis of 6,7-dihydroxynonan-2-one from 6-bromohexan-2-one. You may also use three-carbon alcohols and any required organic or inorganic reagents.
VI.
VII.
X.
IX.
o-chlorocyanobenzene
p-chlorocyanobenzene
C. mixture of o-and p-chlorocyanobenzene
D. m-chlorocyanobenzene
E. mixture of m-and o-chlorocyanobenzene
VIII. The nitration reaction of acetophenone provides:
o-nitroacetophenone
p-nitroacetophenone
mixture of o-and p-nitroacetophenone
D. m-nitroacetophenone
No reaction occurred
During the reaction of benzene with n-propyl chloride and aluminum chloride as
catalyst, the electrophilic species undergoing reaction with benzene is:
A.
B.
C.
iso-propyl carbocation
D.
sec-butyl carbocation
E.
iso-butyl carbocation
The reaction of benzonitrile with chlorine in the presence of iron(III) chloride as a
catalyst provides:
A.
B.
ARCDE
A.
B.
C.
E.
Conversion of benzene into m-bromoaniline is achieved with the following sets of
reagents arranged in right order:
A.
C.
B.
D.
A.
B.
C.
n-propyl carbocation
tert-butyl carbocation
bromine and iron(III) bromide, nitric acid and sulfuric acid, tin, hydrochloric acid,
heat
nitric acid and sulfuric…
Chapter 21 Solutions
ORGANIC CHEMISTRY
Ch. 21 - Rank the following compounds in order of...Ch. 21 - Prob. 21.2PCh. 21 - Give the IUPAC name for each aldehyde.Ch. 21 - Prob. 21.4PCh. 21 - Give the IUPAC name for each ketone.Ch. 21 - Prob. 21.6PCh. 21 - Prob. 21.7PCh. 21 - The boiling point of is significantly higher than...Ch. 21 - Which carbonyl group in each pair absorbs at a...Ch. 21 - Problem 21.10 Draw the structure of all...
Ch. 21 - Prob. 21.11PCh. 21 - Prob. 21.12PCh. 21 - Prob. 21.13PCh. 21 - Prob. 21.14PCh. 21 - Problem 21.15 Draw the product of each...Ch. 21 - Prob. 21.16PCh. 21 - Problem 21.17 Draw the products of the following...Ch. 21 - Problem 21.18 Outline a synthesis of each Wittig...Ch. 21 - Problem 21.19 Draw the products (including...Ch. 21 - Problem 21.20 What starting materials are needed...Ch. 21 - Prob. 21.21PCh. 21 - Problem 21.22 The product formed when reacts with...Ch. 21 - Prob. 21.23PCh. 21 - Prob. 21.24PCh. 21 - Prob. 21.25PCh. 21 - Prob. 21.26PCh. 21 - Prob. 21.27PCh. 21 - Problem 21.28 Draw a stepwise mechanism for the...Ch. 21 - Problem 21.29 Draw the products of each...Ch. 21 - Problem 21.30 Label each compound as an acetal, a...Ch. 21 - Problem 21.31 Draw a stepwise mechanism for the...Ch. 21 - Problem 21.32 Draw the products of each...Ch. 21 - Problem 21.33 Safrole is a naturally occurring...Ch. 21 - Prob. 21.34PCh. 21 - Problem 21.35 How would you use a protecting group...Ch. 21 - Prob. 21.36PCh. 21 - Problem 21.37 Two naturally occurring compounds...Ch. 21 - Problem 21.38 Draw the products of each...Ch. 21 - Prob. 21.39PCh. 21 - Problem 21.40 (a) Give the IUPAC name for A and B....Ch. 21 - 21.41 Rank the following compounds in order of...Ch. 21 - Prob. 21.42PCh. 21 - 21.43 Give the IUPAC name for each compound.
a....Ch. 21 - 21.44 Give the structure corresponding to each...Ch. 21 - Prob. 21.45PCh. 21 - 21.46 Draw the products of each reaction.
a. e....Ch. 21 - Prob. 21.47PCh. 21 - 21.48 Draw all stereoisomers formed in each...Ch. 21 - Prob. 21.49PCh. 21 - What products are formed when each acetal is...Ch. 21 - Prob. 21.51PCh. 21 - Prob. 21.52PCh. 21 - Which compound forms the higher concentration of...Ch. 21 - Prob. 21.54PCh. 21 - Prob. 21.55PCh. 21 - Prob. 21.56PCh. 21 - Prob. 21.57PCh. 21 - Devise a synthesis of each alkene using a Wittig...Ch. 21 - Devise a synthesis of each compound from...Ch. 21 - Prob. 21.60PCh. 21 - Devise a synthesis of each compound from ethanol...Ch. 21 - Prob. 21.62PCh. 21 - Prob. 21.63PCh. 21 - 21.64 Draw a stepwise mechanism for the following...Ch. 21 - 21.65 Draw a stepwise mechanism f or the following...Ch. 21 - Prob. 21.66PCh. 21 - 21.67 Draw a stepwise mechanism for each...Ch. 21 - 21.68 Draw a stepwise mechanism for the following...Ch. 21 - Prob. 21.69PCh. 21 - Prob. 21.70PCh. 21 - Prob. 21.71PCh. 21 - Prob. 21.72PCh. 21 - 21.73 Although the carbonyl absorption of cyclic...Ch. 21 - 21.74 Use the and data to determine the...Ch. 21 - 21.75 A solution of acetone in ethanol in the...Ch. 21 - Compounds A and B have molecular formula ....Ch. 21 - 21.77 An unknown compound C of molecular formula ...Ch. 21 - 21.78 An unknown compound D exhibits a strong...Ch. 21 - Prob. 21.79PCh. 21 - -D-Glucose, a hemiacetal, can be converted to a...Ch. 21 - 21.81 Draw a stepwise mechanism for the following...Ch. 21 - Prob. 21.82PCh. 21 - 21.83 Draw a stepwise mechanism f or the...Ch. 21 - Prob. 21.84PCh. 21 - Prob. 21.85PCh. 21 - 21.86 Draw stepwise mechanism for the following...
Knowledge Booster
Similar questions
- Three arene oxides can be obtained from phenanthrene. a. Draw the structures of the three phenanthrene oxides.b. Draw the structures of the phenols that can be obtained from each phenanthrene oxide.c. If a phenanthrene oxide can lead to the formation of more than one phenol, which phenol will be obtainedin greater yield?d. Which of the three phenanthrene oxides is most likely to be carcinogenic?arrow_forwardDevise a synthesis of each compound from benzene. You may use any other organic or inorganic reagents. NC. Br a. Br NHCOCH3 C. е. Но -соон OH b. I- -CH3 d. f. -N=N- Brarrow_forwardGalantamine, a natural product produced by the amaryllis family of flowering plants, has been used in the early treatment of Alzheimer's disease. In a synthesis of galantamine and related compounds (J. Org. Chem. 2015, 80, 1952-1956), compound 1 was converted into compound 2. Propose an efficient synthesis for the conversion of 1 to 2 A. NaOH MeO D. DMP or PCC G. HBr MeO B. H₂SO4, H₂O, HgSO4 E. Na2Cr₂O7, H₂SO4, H₂O H. 1) O3; 2) DMS H 2 The conversion of 1 to 2 can be performed with some reagent or combination of the reagents listed below. Give the necessary reagents in the correct order for each transformation, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. C. 1) BH3-THF; 2) H₂O2, NaOH F.HBr, ROOR I. TsCl, py Meo I₁, N Me Galanthamine OHarrow_forward
- The biosynthesis of lanosterol from squalene has intrigued chemistssince its discovery. It is now possible, for example, to synthesizepolycyclic compounds from acyclic or monocyclic precursors byreactions that form several C—C bonds in a single reaction mixture.a.) Draw a stepwise mechanism for the following reaction. b.) Show how X can be converted to 16,17-dehydroprogesterone.arrow_forwardIdentify products A and B from the given 1H NMR data.a. Treatment of CH2 = CHCOCH3 with one equivalent of HCl forms compound A. A exhibits the following absorptions in its 1H NMR spectrum: 2.2 (singlet, 3 H), 3.05 (triplet, 2 H), and 3.6 (triplet, 2 H) ppm. What is the structure of A?b. Treatment of acetone [(CH3)2C = O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1 H) ppm. What is the structure of B?arrow_forwardThe biosynthesis of lanosterol from squalene has intrigued chemists since its discovery. It is now possible, for example, to synthesize polycyclic compounds from acyclic or monocyclic precursors by reactions that form several C—C bonds in a single reaction mixture. a. Draw a stepwise mechanism for the following reaction.b. Show how X can be converted to 16,17-dehydroprogesterone.arrow_forward
- Devise a synthesis of each compound from benzene. You may use any other organic or inorganic reagents. NC. Br a. Br е. НО -COOH C. `NHCOCH3 OH b. I- -CH3 d. f. -N=N- -H- Brarrow_forwardPlease provide the reagent (A) and the product (B) of the following scheme. A H3O* HO. Eto. EtO. H. B A HO. А: LIAIH4, B: HO. A: LIAIH4, B: HO, А: NaBH4, B: HO. А: NaBH4, B:arrow_forwardhelp me pleasearrow_forward
- Which compound will react most rapidly with acetaldehyde? A.propylmagnesium chloride B.cyclopropyl magnesium iodide C.propenylmagnesium bromide D.propynylmagnesium bromidearrow_forwardGalantamine, a natural product produced by the amaryllis family of flowering plants, has been used in the early treatment of Alzheimer's disease. In a synthesis of galantamine and related compounds (J. Org. Chem. 2015, 80, 1952-1956), compound 1 was converted into compound 2. Propose an efficient synthesis for the conversion of 1 to 2 A. NaOH MeO D. DMP or PCC G. HBr 1 MeO B. H₂SO4, H₂O, HgSO4 E. Na₂Cr₂O7, H₂SO4, H₂O H. 1) O3; 2) DMS H 2 x I. TsCl, py The conversion of 1 to 2 can be performed with some reagent or combination of the reagents listed below. Give the necessary reagents in the correct order for each transformation, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. C. 1) BH3-THF; 2) H₂O2, NaOH F.HBr, ROOR = MeO Ill. N Me Galanthamine OHarrow_forwardChoose the reagents that can be used to perform the following transformation: Select one: a. "OH, H₂O ...OH e. OH b. H3O+ X c. Na₂Cr₂O7, H₂SO4 d. KMnO4, OH Both -OH, H₂O and H3O+ (separately) will work.arrow_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 LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
![Text book image](https://www.bartleby.com/isbn_cover_images/9781305580350/9781305580350_smallCoverImage.gif)
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
![Text book image](https://www.bartleby.com/isbn_cover_images/9780618974122/9780618974122_smallCoverImage.gif)
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
![Text book image](https://www.bartleby.com/isbn_cover_images/9781305080485/9781305080485_smallCoverImage.gif)