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Number of optically active compounds among the products of ozonolysis

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2

$begingroup$

The number of optically active compound(s) obtained upon complete ozonolysis of
the following optically active compound is

In the question, I broke all the double bonds and added a $ce{-CHO}$ group according to the question (ozonolysis).
Checking for the optically active compounds I found two of them:

But the solution has given only one compound! Can you please help me with this?

organic-chemistry stereochemistry ozone

share|improve this question

edited 4 hours ago

andselisk♦

21.6k77 gold badges7575 silver badges144144 bronze badges

asked 13 hours ago

Asad AhmadAsad Ahmad

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$endgroup$

add a comment | 

2

$begingroup$

The number of optically active compound(s) obtained upon complete ozonolysis of
the following optically active compound is

In the question, I broke all the double bonds and added a $ce{-CHO}$ group according to the question (ozonolysis).
Checking for the optically active compounds I found two of them:

But the solution has given only one compound! Can you please help me with this?

organic-chemistry stereochemistry ozone

share|improve this question

edited 4 hours ago

andselisk♦

21.6k77 gold badges7575 silver badges144144 bronze badges

asked 13 hours ago

Asad AhmadAsad Ahmad

1633 bronze badges

$endgroup$

add a comment | 

$begingroup$

The number of optically active compound(s) obtained upon complete ozonolysis of
the following optically active compound is

In the question, I broke all the double bonds and added a $ce{-CHO}$ group according to the question (ozonolysis).
Checking for the optically active compounds I found two of them:

But the solution has given only one compound! Can you please help me with this?

organic-chemistry stereochemistry ozone

share|improve this question

edited 4 hours ago

andselisk♦

21.6k77 gold badges7575 silver badges144144 bronze badges

asked 13 hours ago

Asad AhmadAsad Ahmad

1633 bronze badges

$endgroup$

share|improve this question

edited 4 hours ago

andselisk♦

21.6k77 gold badges7575 silver badges144144 bronze badges

asked 13 hours ago

Asad AhmadAsad Ahmad

1633 bronze badges

share|improve this question

edited 4 hours ago

andselisk♦

21.6k77 gold badges7575 silver badges144144 bronze badges

asked 13 hours ago

Asad AhmadAsad Ahmad

1633 bronze badges

edited 4 hours ago

andselisk♦

21.6k77 gold badges7575 silver badges144144 bronze badges

edited 4 hours ago

andselisk♦

21.6k77 gold badges7575 silver badges144144 bronze badges

asked 13 hours ago

Asad AhmadAsad Ahmad

1633 bronze badges

asked 13 hours ago

Asad AhmadAsad Ahmad

1633 bronze badges

2 Answers
2

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4

$begingroup$

The given answer is correct. The product scheme you drew is correct as well. However, as I marked in your scheme (see below), products A and B are essentially the same enanthiomer (both have (2S)-configuration). The compounds you have drown in right-hand side are also an identical compound, which is not optically active. Therefore, ozonolysis has given only one optically active compound.

share|improve this answer

edited 10 hours ago

answered 10 hours ago

Mathew MahindaratneMathew Mahindaratne

10.3k11 gold badge1212 silver badges3737 bronze badges

$endgroup$

add a comment | 

3

$begingroup$

Ozonolysis of the given compound gives $ce{I}$ , $ce{II}$ , $ce{III}$ and $ce{IV}$.

• 
  $ce{I}$ and $ce{II}$ are Homomers and have same configuration "S" and therefore identical (as shown in the figure).


• 
  $ce{III}$ and $ce{IV}$ are achiral . Therefore , the total number of optically
  active compounds formed after ozonolysis is $ce{= 1}$.

share|improve this answer

edited 2 hours ago

answered 2 hours ago

Chakravarthy KalyanChakravarthy Kalyan

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$endgroup$

add a comment | 

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4

$begingroup$

The given answer is correct. The product scheme you drew is correct as well. However, as I marked in your scheme (see below), products A and B are essentially the same enanthiomer (both have (2S)-configuration). The compounds you have drown in right-hand side are also an identical compound, which is not optically active. Therefore, ozonolysis has given only one optically active compound.

share|improve this answer

edited 10 hours ago

answered 10 hours ago

Mathew MahindaratneMathew Mahindaratne

10.3k11 gold badge1212 silver badges3737 bronze badges

$endgroup$

add a comment | 

4

$begingroup$

The given answer is correct. The product scheme you drew is correct as well. However, as I marked in your scheme (see below), products A and B are essentially the same enanthiomer (both have (2S)-configuration). The compounds you have drown in right-hand side are also an identical compound, which is not optically active. Therefore, ozonolysis has given only one optically active compound.

share|improve this answer

edited 10 hours ago

answered 10 hours ago

Mathew MahindaratneMathew Mahindaratne

10.3k11 gold badge1212 silver badges3737 bronze badges

$endgroup$

add a comment | 

$begingroup$

The given answer is correct. The product scheme you drew is correct as well. However, as I marked in your scheme (see below), products A and B are essentially the same enanthiomer (both have (2S)-configuration). The compounds you have drown in right-hand side are also an identical compound, which is not optically active. Therefore, ozonolysis has given only one optically active compound.

share|improve this answer

edited 10 hours ago

answered 10 hours ago

Mathew MahindaratneMathew Mahindaratne

10.3k11 gold badge1212 silver badges3737 bronze badges

$endgroup$

share|improve this answer

edited 10 hours ago

answered 10 hours ago

Mathew MahindaratneMathew Mahindaratne

10.3k11 gold badge1212 silver badges3737 bronze badges

answered 10 hours ago

Mathew MahindaratneMathew Mahindaratne

10.3k11 gold badge1212 silver badges3737 bronze badges

answered 10 hours ago

Mathew MahindaratneMathew Mahindaratne

10.3k11 gold badge1212 silver badges3737 bronze badges

3

$begingroup$

Ozonolysis of the given compound gives $ce{I}$ , $ce{II}$ , $ce{III}$ and $ce{IV}$.

• 
  $ce{I}$ and $ce{II}$ are Homomers and have same configuration "S" and therefore identical (as shown in the figure).


• 
  $ce{III}$ and $ce{IV}$ are achiral . Therefore , the total number of optically
  active compounds formed after ozonolysis is $ce{= 1}$.

share|improve this answer

edited 2 hours ago

answered 2 hours ago

Chakravarthy KalyanChakravarthy Kalyan

2,67455 silver badges2323 bronze badges

$endgroup$

add a comment | 

3

$begingroup$

Ozonolysis of the given compound gives $ce{I}$ , $ce{II}$ , $ce{III}$ and $ce{IV}$.

• 
  $ce{I}$ and $ce{II}$ are Homomers and have same configuration "S" and therefore identical (as shown in the figure).


• 
  $ce{III}$ and $ce{IV}$ are achiral . Therefore , the total number of optically
  active compounds formed after ozonolysis is $ce{= 1}$.

share|improve this answer

edited 2 hours ago

answered 2 hours ago

Chakravarthy KalyanChakravarthy Kalyan

2,67455 silver badges2323 bronze badges

$endgroup$

add a comment | 

$begingroup$

Ozonolysis of the given compound gives $ce{I}$ , $ce{II}$ , $ce{III}$ and $ce{IV}$.

• 
  $ce{I}$ and $ce{II}$ are Homomers and have same configuration "S" and therefore identical (as shown in the figure).


• 
  $ce{III}$ and $ce{IV}$ are achiral . Therefore , the total number of optically
  active compounds formed after ozonolysis is $ce{= 1}$.

share|improve this answer

edited 2 hours ago

answered 2 hours ago

Chakravarthy KalyanChakravarthy Kalyan

2,67455 silver badges2323 bronze badges

$endgroup$

share|improve this answer

edited 2 hours ago

answered 2 hours ago

Chakravarthy KalyanChakravarthy Kalyan

2,67455 silver badges2323 bronze badges

answered 2 hours ago

Chakravarthy KalyanChakravarthy Kalyan

2,67455 silver badges2323 bronze badges

answered 2 hours ago

Chakravarthy KalyanChakravarthy Kalyan

2,67455 silver badges2323 bronze badges