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Chapter 18: Q26P (page 950)

Show what alcohols and carbonyl compounds give the following derivatives.

(a)

(b)

(c)

(d)

(e)

(f)

Short Answer

Expert verified

(a)Generally in presence of base like TsOH this is formed.


(b)This is obtained in presence of H+,

(c)This is produced in presence acid catalyst like H+,


(d)This is also formed in presence of H+,


(e)This is formed in presence of H+,


(f) This is results in presence of H+,



Fig (6)

Step by step solution

01

Details explanation of reactants

(a)

Ketones and aldehydes react with water to form hydrates, they also react with alcohols to form acetals.

02

Details explanation of reactants

(b)

03

Details explanation of reactants 

(c)

In the formation of an acetal, two molecules of alcohol add to the carbonyl group, and one molecule of water is eliminated.

04

Details explanation of reactants 

(d)

Acid catalysed hydration gives this product.

05

Details explanation of reactants 

(e)

In the reaction of tetrahydro-2H-pyran-2-one and cyclohexanol in presence of H+, produced this product.

06

Details explanation of reactant

(f)

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Most popular questions from this chapter

Question: Within each set of structures, indicate which will react fastest, and which slowest, toward nucleophilic addition in basic conditions.

Like other strong nucleophiles, triphenylphosphine attacks and opens epoxides. The initial product (a betaine) quickly cyclizes to an oxaphosphetane that collapses alkene and triphenylphospine oxide.

  1. Show each step in the reaction of trans-2,3-epoxybutane with triphenylphospine to give but-2-ene. What is the stereochemistry of the double bond in the product?
  2. Show how this sequence might be used to convert cis-cyclooctene to trans-cyclooctene.

Sodium triacetoxyborohydride, NaBHOAc3, is a mild reducing agent that reduces aldehydes more quickly than ketones. It can be used to reduce aldehydes in the presence of ketones, such as in the following reaction:

(a) Draw a complete Lewis structure for sodium triacetoxyborohydride.

(b) Propose a mechanism for the reduction of an aldehyde by sodium triacetoxyborohydride.

Question. The mass spectrum of unknown compound A shows a molecular ion at m/z 116 and prominent peaks at m/z 87 and m/z 101. Its UV spectrum shows no maximum above 200 nm. The IR and NMR spectra of A follow. When A is washed with dilute aqueous acid, extracted into dichloromethane , and the solvent evaporated, it gives a product B. B shows a strong carbonyl signal at 1715 cm-1in the IR spectrum and a weak maximum at 274nm(E =16) in the UV spectrum. The mass spectrum of B shows a molecular ion of m/z 72. Determine the structures of A and B, and show the fragmentation to account for the peaks at m/z 87 and 101.

Which of the following compounds would give a positive Tollens test? (Remember that the Tollens test involves mild basic aqueous conditions)

(a) CH3CH2COCH3

(b) CH3CH2CHO

(c) CH3CH2CH=CHCH=CHOH

(d) CH3CH2 CH2CH(OH)OCH3

(e) CH3CH2 CH2CH(OCH3)2

(f)

See all solutions

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