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 24.21P
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
The 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
C4H16
What are the products of the catalytic hydrogenation reactions shown below? Explain the
differences using key intermediates as needed.
Na / NH3
H2
Lindlar Catalyst
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
- Draw the structure of zinc 3,7,11- trimethyldodecanoate. • Consider E/Z stereochemistry of alkenes. opy aste ノ/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_forwardQ1/Do as required: 1-The role of H2SO4 in Preparation of Nitrobenzene. Explain 2- Preparation of Nitrobenzene in cool phase. 3-In an experiment Hydrolysis of Acetanilide What color does the litmus paper change to and why? 4-When acetanilide reacts with bromine (x), acctanilide gives p-bromo acetanil 5- why used strongly alkaline (NaOH)in Preparation of Aniline?arrow_forward
- Optically active (R)-2-bromobutane can be converted to 2-butanol under either conditions A or conditions B. Describe the stereochemistry of the product solutions for the two different conditions.arrow_forward7. For each pair of compounds, say which compound is the best SN2 substrate.(a) 2-methyl-1-iodopropane or tert-butyl iodide(b) cyclohexyl bromide or 1-bromo-1-methylcyclohexane(c) 2-bromobutane or isopropyl bromide(d) 1-chloro-2,2-dimethylbutane or 2-chlorobutane(e) 1-iodobutane or 2-iodopropanearrow_forwardDraw the major organic product you would expect to isolate from the reaction of 3-ethyl-5-methyl-4- oxohexanoic acid with a complex of borane with THE followed by H3O+H3O+.arrow_forward
- The specific angle of rotation of (R)-2-bromobutane is -23.1°. Treatment of (R)-2-bromobutane with potassium bromide produces a racemic mixture of (R)- and (S)-2-bromobutane, which is optically inactive. The rate at which the product's angle of rotation decreases is directly proportional to the concentration of KBr. Does this suggest that the reaction takes place by an SN1 or an SŅ2 mechanism? Explain.arrow_forwardExplain the difference of reactivities for solvolysis of cis and trans - 4 -t - butyl cyclohexyl tosylate with the help of energy profile diagram. Draw an energy profile diagram Pleasearrow_forwardThe reaction of 1- methylcyclopentene with mercuric trifluoroacetate in ethanol followed by reduction with sodium borohydride gives 1-ethoxy-1- methylcyclopentane. The -OH peak in the IR shows up at 1700 cm-1 as a sharp peak. (S)-2-bromohexane is the product of the reaction of (S)-2-hexanol with PBr3. The 1H NMR spectrum of 1- pentanol will show a peak for the H atom of the -OH group at 10 ppm delta. A tosylate is a great protecting group for an alcohol. The Williamson ether synthesis is an SN2 reaction of an alkoxide ion with a primary alkyl halide. Thionyl chloride converts ketones into alkyl halides. In an oxidation reaction, the oxygen content of our organic molecule decreases. ✓ [Choose ] False True [Choose ] [Choose ] [Choose ] [Choose ] [Choose ] [Choose ] [Choose ]arrow_forward
- In the acid-catalyzed dehydration of 2-methyl-1-propanol, what carbocation would be formed if a hydride shift accompanied cleavage of the carbon–oxygen bond in the alkyloxonium ion? What ion would be formed as a result of a methyl shift? Which pathway do you think will predominate, a hydride shift or a methyl shift?arrow_forward1. Bicyclic keto compounds such as camphor react predictably with nucleophiles according to steric influences; this effect has been termed steric approach control. In contrast, the reaction of nucleophiles with simple acyclic and monocyclic keto compounds are influenced primarily by thermodynamic factors; this effect has been termed product development control. Given the following reaction, predict the identity of the major product and provide a rationale for your selection. ОН NABH4 t-Bu. t-Bu t-Bu. ELOH 1 2arrow_forwardDraw the sigma complex for the formation of the bromonium electrophile with proper resonance forms for the meta bromination of toluene and for the para bromination of toluene.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
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning