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Full Mechanism of Tollen's Test with the following compounds: 1. Heptaldehyde (heptanal) 2. Acetone (dimethyl ketone)...

Full Mechanism of Tollen's Test with the following compounds:

1. Heptaldehyde (heptanal)

2. Acetone (dimethyl ketone)

3. Benzaldehyde

4. Ethyl acetate

5. Benzoic acid

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Answer #1

Tollen's reagent is mild oxidizing agent, it oxidizes aldehydes, terminal alkykne, alpha-hydroxy ketone because hydrogen is active easily replace and oxidizes even with mild ox. agent.

But ketones do not oxidize by mildox. agent due to low reactivity =, 2 alkyl groups are attached (+I effect).

ester and benzoic acid do not give this test.

1. Heptanal oxidizes to its acid.

Acetone does not react with this.

3. Benzaldehyde also oxidizes to benzoic acid.

4. ethyl acetate do not give this test.

5. benzoic acid do not give this test.

Aldehyde treats with T.R., forms silver mirror means silver ion is reduced to silver precipitate (Grey-silver)

same mechanism occurs for heptanal and benzaldehyde, redox reaction both oxidizes and T.R. will be reduced.

Here R= -C6H13 for heptanal

R= -C6H5 phenyl for benzaldehyde

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