What does the ozonolysis followed by hydrolysis of an unsymmetrical, unbranched alkene form?

I believe the answer is aldehydes but get a second opinion. Branched gives, I believe, an aldehyde and a ketone.

a very poisonous compound found in certain plants. it molecular formula is C23H22N2Cl2. how many degrees of unsaturation does it contain?

A.)14
B.)12
C.)13
D.)6
E.)none of these

14

To determine the product of the ozonolysis followed by hydrolysis of an unsymmetrical, unbranched alkene, we need to understand the reaction steps involved.

Ozonolysis is a chemical reaction that involves the cleavage of carbon-carbon double bonds using ozone (O3). It generates ozonides, which are unstable intermediates. In the case of an unsymmetrical, unbranched alkene, ozonolysis gives an ozonide mixture, consisting of two different fragments.

The next step is the hydrolysis of the ozonide mixture. This step involves treating the ozonide with a reducing agent, typically dimethyl sulfide (CH3)2S, to convert it into two separate carbonyl compounds.

The specific products obtained from the ozonolysis followed by hydrolysis of an unsymmetrical, unbranched alkene depend on the alkene's structure. However, we can analyze the possibilities using a generic unsymmetrical, unbranched alkene, R1R2C=CR3R4, where R represents any substituent or hydrogen atom.

Let's consider the possible scenarios:

1. If R1 and R2 are different and R3 and R4 are different:

The ozonolysis step will result in the formation of two ozonide fragments: R1R2CO and R3R4C=O. The subsequent hydrolysis step will convert these ozonides into two separate carbonyl compounds: R1R2COH and R3R4CHO.

2. If R1 and R2 are different but R3 and R4 are the same (or vice versa):

In this case, the ozonolysis step will generate one ozonide fragment and one aldehyde. For example, if R1 and R2 differ, the ozonides produced will be R1R2CO and R4C=O. The hydrolysis step will then convert R1R2CO into an acid: R1R2COOH.

3. If both R1 and R2 are the same and both R3 and R4 are the same:

In this scenario, the ozonolysis step will yield two identical ozonide fragments: R1R2CO. After hydrolysis, both ozonides will be converted into the same carbonyl compound: R1R2COOH.

So, the final products of ozonolysis followed by hydrolysis will depend on the specific alkene's structure. The reaction's outcome can be determined by identifying the substituents on the carbon atoms involved and following the ozonolysis and hydrolysis reaction steps described above.