Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Question
Chapter 24.SE, Problem 76AP
Interpretation Introduction
Interpretation:
How to convert tropidene in to tropilidene (1,3,5-cycloheptatriene) is to be shown.
Concept introduction:
Two successive Hofmann elimination reactions of with quarternary ammonium salt of tropidene will yield tropilidene.
To show:
How to convert tropidene in to tropilidene (1,3,5-cycloheptatriene).
Answer:
The conversion of tropidene in to tropilidene (1,3,5-cycloheptatriene) is given below.
Explanation:
Tropidene when treated with excess of methyl iodide yields a quartenary ammonium salt which undergoes Hofmann elimination when heated with Ag2O and water to produce N,N-dimethylcycloheptadiene. Methylation of the diene with excess of methyl iodide yields another quartenary ammonium salt which undergoes Hofmann elimination reaction to yield tropilidene.
Conclusion:
The conversion of tropidene in to tropilidene (1,3,5-cycloheptatriene) is given below.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Q5.
What product is formed when cyclohexanone is reacted with each of the
following reagents?
MgBr
KCN
H30*
H30
NABH4
H;O*
Ch19-5: Which of the compounds is the intermediate called hemiacetal of the
following reaction?
요
HO OH H₂SO
(-H₂O)
OH
HO
OH
HO
HOO
O
OH
OH
The following isomerization reaction, drawn using D-glucose as starting material, occurs with all aldohexoses in the presence of
base. Draw a stepwise mechanism that illustrates how each compound is formed.
сно
сно
сно
CH2OH
C=0
H-
OH
H-
-OH
но-
H-
но
H-
"OH
но
H-
Но
H-
но
H-
H-
-H-
H20
H-
HO-
O-
H-
-O-
H-
-OH
-O-
OH
ČHOH
CH,OH
ČH2OH
ČH2OH
(recovered
starting material)
D-glucose
Chapter 24 Solutions
Organic Chemistry
Ch. 24.1 - Name the following compounds:Ch. 24.1 - Prob. 2PCh. 24.1 - Prob. 3PCh. 24.3 - Prob. 4PCh. 24.3 - The benzylammonium ion (C6H5CH2NH3+) has pKa =...Ch. 24.4 - Prob. 6PCh. 24.5 - Prob. 7PCh. 24.6 - Prob. 8PCh. 24.6 - Prob. 9PCh. 24.6 - Show two methods for the synthesis of dopamine, a...
Ch. 24.6 - Prob. 11PCh. 24.6 - Prob. 12PCh. 24.6 - Prob. 13PCh. 24.7 - Prob. 14PCh. 24.7 - Prob. 15PCh. 24.8 - Prob. 16PCh. 24.8 - Propose syntheses of the following compounds from...Ch. 24.8 - How would you prepare the following compounds from...Ch. 24.8 - Prob. 19PCh. 24.9 - Draw an orbital picture of thiazole. Assume that...Ch. 24.9 - Prob. 21PCh. 24.9 - Prob. 22PCh. 24.9 - Which nitrogen atom in the hallucinogenic indole...Ch. 24.9 - Prob. 24PCh. 24.10 - Prob. 25PCh. 24.SE - Name the following amines, and identify each as...Ch. 24.SE - The following compound contains three nitrogen...Ch. 24.SE - Name the following amine, including R, S...Ch. 24.SE - Prob. 29VCCh. 24.SE - Predict the product(s) for each reaction below and...Ch. 24.SE - Predict the product(s) and provide the complete...Ch. 24.SE - Prob. 32MPCh. 24.SE - Predict the product(s) and provide the mechanism...Ch. 24.SE - The diazotization of aniline first involves the...Ch. 24.SE - Prob. 35MPCh. 24.SE - Prob. 36MPCh. 24.SE - Prob. 37MPCh. 24.SE - Prob. 38MPCh. 24.SE - Choline, a component of the phospholipids in cell...Ch. 24.SE - Prob. 40MPCh. 24.SE - -Amino acids can be prepared by the Strecker...Ch. 24.SE - Prob. 42MPCh. 24.SE - Prob. 43MPCh. 24.SE - Prob. 44MPCh. 24.SE - Propose a mechanism for the following reaction:Ch. 24.SE - Prob. 46MPCh. 24.SE - Name the following compounds:Ch. 24.SE - Prob. 48APCh. 24.SE - Prob. 49APCh. 24.SE - Prob. 50APCh. 24.SE - Histamine, whose release in the body triggers...Ch. 24.SE - Prob. 52APCh. 24.SE - Prob. 53APCh. 24.SE - Prob. 54APCh. 24.SE - Prob. 55APCh. 24.SE - Prob. 56APCh. 24.SE - Prob. 57APCh. 24.SE - Prob. 58APCh. 24.SE - Prob. 59APCh. 24.SE - Prob. 60APCh. 24.SE - Show the products from reaction of p-bromoaniline...Ch. 24.SE - Prob. 62APCh. 24.SE - How would you prepare the following compounds from...Ch. 24.SE - Prob. 64APCh. 24.SE - Phenacetin, a substance formerly used in...Ch. 24.SE - Prob. 66APCh. 24.SE - Draw the structure of the amine that produced the...Ch. 24.SE - Fill in the missing reagents a-e in the following...Ch. 24.SE - Prob. 69APCh. 24.SE - Prob. 70APCh. 24.SE - Deduce the structure of the compound with formula...Ch. 24.SE - Prob. 72APCh. 24.SE - Prob. 73APCh. 24.SE - Prob. 74APCh. 24.SE - Prob. 75APCh. 24.SE - Prob. 76APCh. 24.SE - Propose a structure for the product with formula...Ch. 24.SE - Prob. 78APCh. 24.SE - Prob. 79APCh. 24.SE - Prob. 80APCh. 24.SE - Prob. 81APCh. 24.SE - Prob. 82APCh. 24.SE - Prob. 83APCh. 24.SE - Prob. 84AP
Knowledge Booster
Similar questions
- 19 Which of the following ketoesters can be formed by Dieckmann cyclization? D E B C بلا سلامarrow_forwardTamoxifen is a drug used to prevent and treat breast cancer. What are all the possible metabolic reactions for this drug? Aromatic hydroxylation Epoxidation ON-dealkylation Benzylic hydroxylation O Epoxidation followed by epoxide hydrolysisarrow_forwardDraw the product formed when CH3CH2C=CH is treated with each of the following sets of reagents: (a) H2O, H2SO4, HgSO4; and (b) R2BH, followed by H2O2, HO−.arrow_forward
- Q5. What product is formed when cyclohexanone is reacted with each of the following reagents? MgBr KCN H30 H30 NABH, H30*arrow_forwardH3C a с e H3C -CH2NH2 Provide the missing reagents (a, c, e) and intermediate products (b, d) formed as toluene is converted to the final product.arrow_forwardWhat product is formed when each compound is treated with either Ag2O, NH4OH or Na2Cr2O7, H2SO4, H2O?arrow_forward
- Prostaglandins are a class of eicosanoids, fatty acid derivatives involved in a variety of important phenomena, including fever, inflammation, and pain. The first step in prostaglandin synthesis involves the conversion of the 20-carbon fatty acid arachidonic acid to PGG2 by the enzyme prostaglandin endoperoxide synthase, or cyclooxy: Ibuprofen is one of several inhibitors of cyclooxogenase used therapeutically. Arachidonic acid 20₂ 0.5 1.0 1.5 2.5 3.5 cyclooxrygenase PGG₂ JOH محمد The following kinetic data were obtained for the enzyme cyclooxygenase in the absence of any inhibitor (1), and in the presence of ibuprofen (2) at a concentration of 48 [arachidonic acid] (uM) (1) v(uM/min) (2) v(uM/min) 23.5 32.2 36.9 41.8 44.0 16.67 25.25 30.49 37.04 38.91 Ibuprofen A. Plot the data in standard Michaelis-Menten form as well as in double-reciprocal form. B. Determine Vmax and Km for the enzyme. C. Based on this limited data set, what type of inhibition does ibuprofen likely exhibit?…arrow_forwardH3C₁ a b d e H3C Provide the missing reagents (a, c, e) and intermediate products (b, d) formed as toluene is converted to the final product. CH, NHarrow_forwardH2N Orcinol но A но он a.arrow_forward
- Which of the following is a hemiacetal? ОН ОН A) H;C-C-OH В) Н,С-С—ОСH Н н ОН нс- OCH3 D) H,C-С—ОСН, С) НС-С—ОН ÓCH3 н A Darrow_forwardB-D-Glucose, a hemiacetal, can be converted to a mixture of acetals on treatment with CH,OH in the presence of acid. Draw a stepwise mechanism for this reaction. Explain why two acetals are formed from a single starting material. он он OH CH;OH, HCI HO Но HO HO но + Но + H20 OH OCH3 OH OHOCHS но B-D-glucosearrow_forwardDraw the structure of the following organic compounds. ▪ 7-fluorohept-4-yn-2-ol 3-methoxycyclopent-3-en-1-one 5-ethyl-6-fluoro-7-propoxyhept-2-yne 5-amino-3,3-dimethylcyclohexan-1-one 3-ethoxy-N,N-diethyl-5-oxoheptanamide - ☐ ☐ ■ 1-ethoxy-3-ethyl-N-methylpent-4-en-2-araine 2-amino-5-fluorocyclopentane-1-carboxylic acid acetic 4-fluoro-3-hydroxy-2-methylpentanoic anhydridearrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher: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