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Four compounds have the formula C4H8O, identify possible compounds.

Four compounds have the formula C4H8O. Identify possible compounds (by name or structure). Compounds A and C have similar boiling points; Compounds B and D have significantly lower boiling points than A and C.

A Reacts with oxidizing agents; reacts immediately with bromine; negative Iodoform Test; negative Lucas Test.
B Negative result with oxidizing agents; reacts with bromine only with uv-light; negative Iodoform test; as previously mentioned, has relatively low boiling point.
C Reacts with oxidizing agents; reacts immediately with bromine; gives a positive result to Lucas Test after 8 minutes; shows yellow precipitate result in Iodoform Test
D No reaction with oxidizers; reacts with bromine only when uv-light is present; has positive Iodoform test.

Solution This solution is FREE courtesy of BrainMass!

C4H8O -> Compounds can be aldehyde, ketone, ether, and alcohol
-> Double bond(C=C) or ring or C=O bond

Lucas test = (+) -> secondary or tertiary alcohol

Lodoform test = (+) -> methyl ketone, secondary alcohol(R-CH(OH)-CH3)

A -> Reacts with oxidizing agents -> NOT ketone, ether, or tertiary alcohol
-> Reacts immediately with bromine ? Double bond(C=C)? NOT aldehyde
-> Negative Iodoform Test ? NOT secondary alcohol, ketone
-> Negative Lucas Test ? NOT secondary or tertiary alcohol (again)

Therefore, it can be primary alcohol and there is C=C bond inside the structure.

B -> Negative result with oxidizing agents -> NOT primary or secondary alcohol, or
aldehyde
-> Reacts with bromine only with uv-light -> NO Double bond(C=C)
-> Negative Iodoform Test ? NOT tertiary alcohol, or ketone

Therefore, it can be ether and there is ring in the structure.

C -> Reacts with oxidizing agents -> NOT ketone, ether, or tertiary alcohol
-> Reacts immediately with bromine -> Double bond(C=C) -> NOT aldehyde
-> A positive result to Lucas Test -> secondary alcohol
-> Yellow precipitate result in Iodoform Test -> R-CH(OH)-CH3

Therefore, it can be secondary alcohol and there is C=C bond inside the structure.

D -> No reaction with oxidizers -> NOT primary or secondary alcohol, or aldehyde
-> Reacts with bromine only when uv-light is present -> NO Double bond(C=C)
-> Positive Iodoform test -> methyl ketone

Therefore, it can be ether and there is ring in the structure.

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