Draw the final product from the following six-step reaction sequence.

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Answer 1

Answer #1

Concepts and reason

The concept of nucleophilic substitution reaction, reduction of ester and acetal formation are used in this question.

Initially, explain the stepwise mechanism of the formation of the final product of the given reaction. Then, write the complete reaction and then draw the structure of the final product.

Fundamentals

Nucleophilic substitution reaction:

In this type of reactions, an electron-rich species will attack at the electron-deficient site of an electrophile, and substitute the leaving group.

Reduction of esters:

Carboxylic acids or esters reduced to corresponding alcohol by a strong reducing reagent like lithium aluminum hydride (LiAlH,) .

LiAlH4
R
OH + ROH
K OR
Carboxylic acid
H30+
Alcohol
or
Ester

Acetal formation:

Ketones or aldehydes react with ethylene glycol to form acetal. The general reaction of the formation of an acetal is given as shown below.

НО,
R
R
R
R
Acetal
Ketone
or
Aldehyde

The curved arrow mechanism for the formation of the final product of the six-step reaction is as follow:

--
OCH;
OCH
0
0
14. LiAIH
5. HO
HO
HO
xx
HO*

The complete reaction of the formation of the final product shown below.

1. NaOCH
2. Br
Br
x
3. NaOCH;
4. LiAlH4
5. HO
dimethyl malonate
3,3-dimethyl-2,4-dioxaspiro[5.5 Jundecane
, H3O+ (cat.)

Ans:

The structure of the final product of the given reaction is as follows:

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Answer 2

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Draw the final product from the following six-step reaction sequence.

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