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An organic compound (A) (C(10)H(20)) on ...

An organic compound (A) `(C_(10)H_(20))` on reductive ozonolysis gives `2-` methyl butanal. Based on this information, answer the following question.
The total number of stereoisomers possible for (A) is :

A

8

B

7

C

6

D

4

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem, we need to determine the total number of stereoisomers possible for the organic compound (A) with the formula \( C_{10}H_{20} \), which on reductive ozonolysis gives 2-methylbutanal. Here’s a step-by-step breakdown: ### Step 1: Identify the structure of the product The product of the ozonolysis is 2-methylbutanal. The structure of 2-methylbutanal can be represented as follows: ``` CH3 | CH3-CH-CHO | CH2-CH3 ``` ### Step 2: Determine the structure of compound (A) Since ozonolysis cleaves double bonds, compound (A) must have a structure that can yield two moles of 2-methylbutanal. The simplest structure that can achieve this is a compound with a double bond that, when cleaved, results in two identical aldehyde products. A possible structure for compound (A) could be: ``` CH3 | CH3-CH=CH-CH2-CH3 ``` This structure has a double bond between the second and third carbon atoms. ### Step 3: Identify chiral centers in compound (A) Next, we need to identify if there are any chiral centers in compound (A). A chiral center is typically a carbon atom that is bonded to four different groups. In the structure of compound (A): - The second carbon (C2) has the following groups: \( CH3, CH, CH2, H \) (which are different). - The third carbon (C3) also has the following groups: \( CH3, CH2, CH, H \) (which are different). Thus, both C2 and C3 are chiral centers. ### Step 4: Calculate the number of stereoisomers The formula to calculate the number of stereoisomers based on the number of chiral centers (n) is given by: \[ \text{Number of stereoisomers} = 2^n \] Here, \( n = 2 \) (since we have two chiral centers). Thus, the number of stereoisomers is: \[ 2^2 = 4 \] ### Step 5: Consider geometric isomerism Since compound (A) has a double bond, it can also exhibit geometric (cis/trans) isomerism. Each geometric isomer can also have the stereoisomers calculated previously. For each of the 4 stereoisomers, there are 2 possible geometric isomers (cis and trans). Therefore, the total number of stereoisomers becomes: \[ 4 \text{ (from chiral centers)} \times 2 \text{ (from geometric isomerism)} = 8 \] ### Final Answer The total number of stereoisomers possible for compound (A) is **8**. ---
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