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Show how you would synthesize from each compound. You may use any necessary reagents.

(a)octan - 1 - ol

(b)non - 1 - ene

(c)oct - 1 - yne

(d)1 - bromoheptane

(e)1 - bromohexane

(f)octanoicacid

(g)ethyloctanoate

Short Answer

Expert verified

The structure of is shown below.

octanal

Step by step solution

01

Octanal

The structure of is shown below.

octanal

02

Synthetic methodology

(a) PCC (pyridinium chlorochromate) oxidizes the primary alcohol ( octan - 1 - ol) to aldehyde ( octanal)

localid="1664867875553" reactiona

(b) Ozone cleaves the double bonds similar to permanganate to give ketones and aldehydes. non - 1 - eneundergoes ozonolysis to give the products as octanal andformaldehyde

reactionb

(c) Hydration of alkyne ( oct - 1 - yne) takes place on treatment with disiamylborane

Sia2BH) in presence of hydrogen peroxide (
H2O2) to give

localid="1664868086642" reactionc

(d) 1 - bromoheptaneon treatment with sodium cyanide followed by acid-catalyzed hydration forms octanal .

reactiond

(e) 1 - bromohexaneon treatment with magnesium in ether forms a Grignard product which further reacts with an epoxide (oxirane) and H3O+gives the product as octanal

reactione

(f) Octanoicacid undergoes reduction with lithium aluminum hydride(LiAlH4) followed by oxidation with PCC (pyridinium chlorochromate) gives the final product asoctanal .

reactionf

(g) DIBAL-H reduces ethyloctanoate to an aldehyde (octanal ).

reactiong

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Most popular questions from this chapter

The IR spectrum of trans-oct-2-enoic acid is shown. Point out the spectral characteristics that allow you to tell that this is a carboxylic acid, and show which features lead you to conclude that the acid is unsaturated and conjugated.

Glutathione (GSH) is a tripeptide that serves as a mild reducing agent to detoxify peroxides and maintain the cysteine residues of hemoglobin and other red blood cell proteins in the reduced state. Complete hydrolysis of glutathione gives Gly, Glu, and Cys. Treatment of glutathione with carboxypeptidase gives glycine as the first free amino acid released. Treatment of glutathione with 2,4-dinitrofluorobenzene (Sanger reagent, Problem 24-21, page 1282), followed by complete hydrolysis, gives the 2,4-dinitrophenyl derivative of glutamic acid. Treatment of glutathione with phenyl isothiocyanate does not give a recognizable phenylthiohydantoin, however.

(a) Propose a structure for glutathione consistent with this information. Why would glutathione fail to give a normal product from Edman degradation, even though it gives a normal product from the Sanger reagent followed by hydrolysis?

(b) Oxidation of glutathione forms glutathione disulfide(GSSG). Propose a structure for glutathione disulfide, and write a balanced equation for the reaction of glutathione with hydrogen peroxide.

Question: Predict the products (if any) of the following acid-base reactions.

  1. formic acid + ammonia
  2. terphthalic acid + excess NaOH
  3. p-toluic acid + sodium trifluoroacetate
  4. α-chloropropionic acid + sodium propionate
  5. benzoic acid + potassium phenoxide

Question: Oxidation of a primary alcohol to an aldehyde usually gives some over-oxidation to the carboxylic acid. Assume you have used PCC to oxidize pentan-1-ol to pentanal.

(b). Which of the expected impurities cannot be removed from pentanal by acid-base extractions? How would you remove this impurity?

Question: Propose a mechanism for conversion of the dianion to the ketone under mildly acidic conditions.

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