Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Question
Chapter 24, Problem 24.22P
Interpretation Introduction
Interpretation:
Concept Introduction:
In catalytic allylic alkylation, a nucleophile, enolate of a doubly activated
Stereochemistry at the alkylation carbon is retained.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
b) Optical isomers can often be formed during these reactions. For products A-H
indicate how many different optical isomers you expect to form for each
from these reactions (you do not have to indicate whether they are diastereomers/enantiomers).
c) In the preparation of substance D by ozonolysis, the second step is necessary treatment of the reaction
mixture with zinc in acetic acid. If we forgot this step, we would get substance V instead of substance D, which
would probably explode when isolated. What is the structure of substance V?
*24
X
1: ozone
V
e) What products do you expect to form if they react with alkene X: I - HBr in diethyl ether; II - Brl in methanol; III -
PhSCI in diethyl ether; IV - Selectfluor in methanol.
P
M
EtOH
NA
EtONa
PhSNa
EtOH E
H+
O
TsCl
Pyridín
F-
T2, Pd/C
G4
mCPBA
H₂SO4
10 %, H₂O
1: BH3
H◄
2: H₂O₂
ill
X
Br₂
cyclohexane
HCI
A
> В
B
HBr
warmth,
benzoylperoxid
1: ozone
2: Zn, ACOH
Mg
THF
с
D
D₂O
K
I + J
NaOH
4) In a two-step reaction of [PtCl4]² with NO₂¯followed by NH3, what will be the
disposition of the two remaining chlorides in the product (cis or trans?). Explain your
answer.
3. It is required to introduce a halogen group to a five membered ring, thiophene. Discuss
the reaction mechanism involved in the reaction by selecting a suitable halogen group and
analyze why a particular substituted product obtained after the reaction is predominant
over the other possible product(s) with the help of reactions.
To meet the ever increasing demand of global population, the demand for textile products and
consumption of dyes by these industries is increasing.
Chapter 24 Solutions
Organic Chemistry
Ch. 24.3 - Prob. 24.1PCh. 24.3 - Prob. 24.2PCh. 24.4 - Prob. 24.3PCh. 24.5 - Show how the following compound can be prepared...Ch. 24.5 - Prob. 24.5PCh. 24.5 - Prob. 24.6PCh. 24.6 - Prob. 24.7PCh. 24 - Prob. 24.8PCh. 24 - Prob. 24.9PCh. 24 - Prob. 24.10P
Ch. 24 - Treatment of cyclohexene with iodobenzene under...Ch. 24 - Prob. 24.12PCh. 24 - Prob. 24.13PCh. 24 - The aryl diene undergoes sequential Heck reactions...Ch. 24 - Heck reactions take place with alkynes as well as...Ch. 24 - Prob. 24.16PCh. 24 - The following transformation involves a series of...Ch. 24 - Show the sequence of Heck reactions by which the...Ch. 24 - Prob. 24.19PCh. 24 - Write the steps that are critical in the following...Ch. 24 - Prob. 24.21PCh. 24 - Prob. 24.22PCh. 24 - Prob. 24.23PCh. 24 - Show how the following compound could be prepared...Ch. 24 - It is typically very difficult to do a...Ch. 24 - The compound eutypine is an antibacterial agent...Ch. 24 - Prob. 24.27PCh. 24 - Prob. 24.28PCh. 24 - Prob. 24.29PCh. 24 - Prob. 24.30PCh. 24 - Prob. 24.31PCh. 24 - Prob. 24.32PCh. 24 - Prob. 24.33PCh. 24 - The following transformation can be accomplished...Ch. 24 - Prob. 24.35PCh. 24 - Prob. 24.36PCh. 24 - Prob. 24.37PCh. 24 - Prob. 24.38PCh. 24 - E. J. Coreys 1964 total synthesis of...Ch. 24 - Prob. 24.40P
Knowledge Booster
Similar questions
- Possible alternative brominations include: Veratrole (1,2-dimethoxybenzene) to 1,2-dibromo-4,5-dimethoxybenzene; 4-Methylacetanilide to 2-bromo-4-methylacetanilide; 2-Methylacetanilide (made in experiment S.1) to 4-bromo-2-methylacetanilide; Vanillin to 5-bromovanillin; Acetanilide to 4-bromoacetanilide; a. b. C. d. e. EXPERIMENT S4: BROMINATION OF AROMATIC COMPOUNDS Certain other acetanilides made in experiment S.1 may also be used as precursors in this experiment. Estimated time: 1 afternoon Associated learning goals: Section 6, LG 6.6; Section 7, LG 7.2 and 7.4 Pre-lab report: complete the standard report form, and answer the following questions. In this experiment, molecular bromine (Br2) is generated from the redox reaction of potassium bromate with hydrobromic acid. Write a balanced equation for this process. Briefly outline the mechanism by which Br2 brominates your aromatic compound. Why do the bromine atoms end up at the positions indicated rather than anywhere else in the…arrow_forward3. cyclohexanone to cyclohexane. A second year chemistry student is assigned a task to prepare compound 2 from compound 1 using lithium aluminium hydride as a reducing agent. However, from the reaction mixture, no traces of product 2 were detected. Explain this observation in detail and suggest an alternative route that will lead to product 2. H 1 CH3 LiAllH4 H O: 2 CH3 quearrow_forwardWhich one of the following statements is FALSE? O The formation of a Grignard reagent requires use of 1 molecule of magnesium metal for every 1 molecule of alkyl bromide used. Organometallic compounds undergo transmetallation to form a less polar carbon-metal bond. O Reductive elimination is the last step in a Pd-mediated cross-coupling reaction. Oxidative addition is when a metal inserts between a carbon-halogen bond. The formation of an organolithium reagent requires use of 1 molecule of lithium metal for every 1 molecule of alkyl bromide used.arrow_forward
- Draw the sigma complexes for the following reaction. Explain why the methoxy group is aN op director and aN activating group. You will have either NiNe or eleveN sigma complexes. осиз Навои HNO3arrow_forward1) л-allylpalladium complexes can provide an alternative to the direct displacement of allylic leaving groups, for the formation of carbon to carbon bonds. i) In regard to л-allylpalladium complexes, provide the reagents and conditions necessary for their preparation. DRAW a general mechanism for their formation and range of reactions. ii) For the below transformations, DRAW the way that it could be achieved using - allylpalladium chemistry. OHarrow_forwardWhen the three benzaldehydes shown below were exposed to HCN under identical conditions it was found that the equilibrium constants, K, for the three cyanohydrin formation reactions were different. Based on principles that govern equilibrium processes for reversible carbonyl addition reactions, place the K values for the three reactions in ascending order (smallest to largest). Briefly justify your answer. (Hint: Recall that electron deficient carbonyls tend to react faster with nucleophiles and have larger equilibrium constants for the addition reaction.) H X O + HCN pH ~ 9-10 X = H, NO₂, OCH 3 OH H+CN Xarrow_forward
- In the early age of the development of Organometallilc Chemistry, the preparation of Organometallic Compound containing M-R(R: alkyl group) bond always led to the decomposition of the M-R bond. It was later known to be caused by the so called “beta-hydrogen elimination” process. Which of the following statements is not correct? This process can be prevented by using all halogenated alkyl group. This process can be prevented by carrying out reaction at high temperature. The Grignard’s reagent, RMgX or R2Mg is stable and does not undergo “b-hydrogen elimination” process. The anti-knocking agent, Pb(C2H5)4 is stable and does not undergo “b-hydrogen elimination” process. The ferrocene, Cp2Fe, is free from the “b-hydrogen elimination” process.arrow_forwardThe Stille coupling reaction is another metal-catalyzed reaction that is a great way to form carbon-carbon bonds. What makes the Stille coupling unique is that it is a carbonylative reaction, meaning CO is inserted into the compound to make a carbonyl group. The mechanism involves oxidative addition, coordination, insertion, transmetallation, and reductive elimination. Suggest a mechanism for the following Stille coupling. OTf Me Si SnBu3 cat. Pd(PH3)4 LICI, 1.1 atm CO C12H20OSIarrow_forwardThe following reaction involves two sequential Heck reactions. Draw structural formu- las for each organopalladium intermediate formed in the sequence and show how the final product is formed. Note from the molecular formula given under each structural formula that this conversion corresponds to a loss of H and I from the starting material. Acetonitrile, CH,CN, is the solvent. 1% mol Pd(OAc), 4% mol Ph,P CH,CN C4H171 C4H16arrow_forward
- 2) Write the products of the following reactions and indicate if they are meso compounds or racemic mixtures. + KMNO4, KOH, cold Ph Ph Ph H2, 1 atm. RT Ni (cat) Pharrow_forwardGive the major organic product(s) for each step of the following reactionarrow_forwardUsing Friedel Crafts alkylation of benzene, a group of scientists discovered marks) compound A, C10H120, an optically inactive compound. They discovered that compound B, C10H12CIO, is produced during the halogenation process. When compound B is reacted with nitric acid, compound C, C10H16CINO3, is formed. While Friedel Crafts alkylation of compound A produces compound D. This compound D was oxidised to produce compound E, CH203 as a major product. Compound F, C12H1402, was produced by Friedel Crafts acylation of compound A. This compound F reacts positively with alkaline iodine and 2,4- dinitrophenylhydrazine. However, it returns negative results for Tollens' and Benedict's tests. Prolonged heating of compound F with acidified potassium manganite (VII) produces compound G, CH.04 (aromatic dicarboxylic acid compound) as a major product and minor products (carbon dioxide and water). Identify the possible structural formulae compounds A to G. How would you distinguish between compounds E…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 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
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning