Concept explainers
(a)
Interpretation: Each double bond in lejimalide B is to be labeled as
Concept introduction: Stereochemistry is defined as the arrangement of molecule in three dimensional and its impact on
The use of prefix
(b)
Interpretation: Each tetrahedral stereogenic center in the given drug is to be labeled as
Concept introduction: Rules for assigning R and S configuration are as follows:
1. The groups are prioritized on the basis of their
2. If the atoms that are attached to the chiral centre are similar to each other, then the priority is given on the basis of the next atom attached.
3. The molecule is oriented in such a manner that the lowest priority group comes at the dashed wedge.
4. If the first three high priority groups are present in a clockwise manner then the molecule is assigned R configuration but if these are present in an anticlockwise manner then the molecule is assigned with S configuration.
(c)
Interpretation: The number of stereoisomers possible for lejimalide B is to be predicted.
Concept introduction: A compound exhibits number of stereoisomers when it contains more than one stereogenic centers. The maximum number of stereoisomers a compound with n number of stereogenic centers can show is
Want to see the full answer?
Check out a sample textbook solutionChapter 10 Solutions
Organic Chemistry (6th Edition)
- Quinapril (trade name Accupril) is used to treat high blood pressure and congestive heart failure. One step in the synthesis of quinapril involves reaction of the racemic alkyl bromide A with a single enantiomer of the amino ester B. (a) What two products are formed in this reaction? (b) Given the structure of quinapril, which one of these two products is needed to synthesize the drug?arrow_forward1arrow_forward4G. 4G 7:41 PM 27 4. Draw structures corresponding to the following names: (a) 2,2-Dimethylpropanoyl chloride (c) 5,5-Dimethylhexanenitrile (e) trans-2-Methylcyclohexanecarboxamide (f p-Methylbenzoic anhydride (b) N-Methylbenzamide (d) tert-Butyl butanoatearrow_forward
- (a) Explain why an alkylamine is more basic than ammonia?(b) How would you convert(i) Aniline to nitrobenzene (ii) Aniline to iodobenzenearrow_forwardWhich compound will undergo nucleophilic aromatic substitution faster when treated with CH3NH₂? (a) CI (b) CIarrow_forwardConsider the tetracyclic compound with rings labeled A–D. (a) Which ring is the most reactive in electrophilic aromatic substitution? (b) Which ring is the least reactive in electrophilic aromatic substitution?arrow_forward
- Draw the mechanisms leading to the major organic product(s) for each of the following reactions. Do all A,B and C with work showing how.arrow_forwardRank the compounds in each of the following groups in order of their reactiv- ity to electrophilic substitution: (b) Phenol, benzene, chlorobenzene, benzoic acid (c) Benzene, bromobenzene, benzaldehyde, anilinearrow_forward(a) Draw two different halo ketones that can form A by an intramolecular alkylation reaction. (b) How can A be synthesized by an acetoacetic ester synthesis? of Aarrow_forward
- (a) Why are alkyl halides insoluble in water? (b) Why is Butan-l-ol optically inactive but Butan-2-ol is optically active? (c) Although chlorine is an electron withdrawing group, yet it is ortho-, Para- directing in electrophilic aromatic substitution reaction. Why?arrow_forwardRank the compounds in each of the following groups in order of their reactivity to electrophilic substitution: (a) Nitrobenzene, phenol, toluene, benzene (b) Phenol, benzene, chlorobenzene, benzoic acid (c) Benzene, bromobenzene, benzaldehyde, anilinearrow_forwardPractice Problem 19.54 Z Your answer is partially correct. Try again. Predict the major product(s) (A - K) from the treatment of acetone with the following compounds (a-c): NH2 HO Eto OEt A: B: C: D: E: F: OH OH но CN G: H: I: J: (a) [H*], excess EtOH, (-H20) Major Product(s): (ь) NaBH4, Meон B Major Product(s): (c) LAH followed by H20 Major Product(s): SHOW HINTarrow_forward
- 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