(a)
Interpretation: The reagents that can be used to achieve the following transformation are to be identified.
Concept introduction: The given compound is a terminal
(b)
Interpretation: The reagents that can be used to achieve each of the following transformations are to be identified.
Concept introduction: The starting alkyne is a compound with five carbon atoms, which to be converted into a seven carbon-containing terminal alkyne, needs to undergo a reaction with such reagents which can facilitate this reaction. Reduction using a poisoned catalyst such as Lindlar’s catalyst, followed by bromination and reaction with an alkynide can yield the desired product.
(c)
Interpretation: The reagents that can be used to achieve each of the following transformations are to be identified.
Concept introduction: The starting material has one more carbon atom than the product. This means the synthesis must have an ozonolysis process, to cleave a carbon-carbon bond. Also, since the product is a
(d)
Interpretation: The reagents that can be used to achieve each of the following transformations are to be identified.
Concept introduction: The starting material has six carbon atoms, and the product has nine carbon atoms. So the synthesis must involve the installation of three carbon atoms and also, the location of the
(e)
Interpretation: The reagents that can be used to achieve each of the following transformations is to be identified.
Concept introduction: The product has two more carbon atoms than the starting material, and the location of the functional group has changed. So, bromination followed by dehydrohalogenation can give a terminal alkene, which on further bromination followed by reaction with an alkynide would yield the desired product.
(f)
Interpretation: The reagents that can be used to achieve each of the following transformation is to be identified.
Concept introduction: The starting material has one more carbon atom than the product. Therefore, the synthesis must employ an ozonolysis process, to cleave a carbon-carbon bond. For the formation of an aldehyde product, an alkene is also required. For this alkene to be formed, the alcohol must be converted to a tosylate, and then after the alkene is formed, it can undergo ozonolysis to yield the product.

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Chapter 11 Solutions
ORGANIC CHEMISTRY-PRINT MULTI TERM
- Q5: Label each chiral carbon in the following molecules as R or S. Make sure the stereocenter to which each of your R/S assignments belong is perfectly clear to the grader. (8pts) R OCH 3 CI H S 2pts for each R/S HO R H !!! I OH CI HN CI R Harrow_forwardCalculate the proton and carbon chemical shifts for this structurearrow_forwardA. B. b. Now consider the two bicyclic molecules A. and B. Note that A. is a dianion and B. is a neutral molecule. One of these molecules is a highly reactive compound first characterized in frozen noble gas matrices, that self-reacts rapidly at temperatures above liquid nitrogen temperature. The other compound was isolated at room temperature in the early 1960s, and is a stable ligand used in organometallic chemistry. Which molecule is the more stable molecule, and why?arrow_forward
- A mixture of C7H12O2, C9H9OCl, biphenyl and acetone was put together in a gas chromatography tube. Please decide from the GC resutls which correspond to the peak for C7,C9 and biphenyl and explain the reasoning based on GC results. Eliminate unnecessary peaks from Gas Chromatography results.arrow_forwardIs the molecule chiral, meso, or achiral? CI .CH3 H₂C CIarrow_forwardPLEASE HELP ! URGENT!arrow_forward
- Identify priority of the substituents: CH3arrow_forwardHow many chiral carbons are in the molecule? OH F CI Brarrow_forwardA mixture of three compounds Phen-A, Acet-B and Rin-C was analyzed using TLC with 1:9 ethanol: hexane as the mobile phase. The TLC plate showed three spots of R, 0.1 and 0.2 and 0.3. Which of the three compounds (Phen-A; Acet-B or Rin-C) would have the highest (Blank 1), middle (Blank 2) and lowest (Blank 3) spot respectively? 0 CH: 0 CH, 0 H.C OH H.CN OH Acet-B Rin-C phen-A A A <arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningIntroduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning


