Draw the structure of the organic product or products formed in the following reaction.

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Question

Draw the structure of the organic product or products formed in the following reaction.

Draw the structure of the organic product or products formed in the following reaction. Include hydrogen atoms. H2C=CH-CH=CH-CH2-Mg-Br 1. H2C-O-CH2 2.H3O+

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Answer 1

Answer #1

?? 1. H2C-CH2 (E)-hepta-4,6-dien-1-ol 2.H, O 3 OH 3-vinylpent-4-en-1-ol

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Answer 2

Answer #2

Concepts and reason

The concepts for the given organic problem are reaction with Grignard reagent and then followed by acidic hydrolysis.

Grignard reagents are organomagnesium halides having the general formula ${\rm{R - MgX}}$ where ${\rm{X}}$ can be ${\rm{Cl,}}\,{\rm{Br,}}\,{\rm{or}}\,{\rm{I}}$ and ${\rm{R}}$ can be an alkyl, alkenyl, alkynl, aralkyl or aryl group or may also be an alicyclic or a heterocyclic group.

The carbon-magnesium bond in a Grignard reagent is a highly polar covalent bond. The magnesium-halogen bond is essentially ionic.

$\mathop {\rm{R}}\limits^{{{\rm{\delta }}^{\rm{ - }}}} {\rm{ - }}\mathop {{\rm{Mg}}}\limits^{{{\rm{\delta }}^{\rm{ + }}}} {\rm{X}}$

Fundamentals

Grignard reagents exhibit nucleophilic substitution and nucleophilic addition reaction, due to the presences of highly polar covalent bond and the ${\rm{R}}$ part of the compound has carbanion character and thus it acts as nucleophile.

Epoxide reacts with Grignard reagents to form addition products which on acidic hydrolysis give primary alcohols.

Mg-Br
H2C CH
CH2
CH
CH
H2C CH CH CH_CH2-MgBr

А.
Mg
Br
НаС
CH2
H2с— сн—сH-— сH—сHа— Mg— Вr
Н2С— сн—сH— CH—СH-—CH2—CH2
А
Нас — сН2—о Mg— Br
Mg-Br
Нас-
CH2
CH CH CH2
-СH—CH—

ОН
Нао*
Нас—сн—сн— сH—сH2—сH—сH2
-CH2— СH2
H2С— сн—сн— сн—сH-
+
- о Mg-
Hас
Hас — сН2-
Br
-CH—ОН
Нао
-СH—СH CH
HаС— сн-
-CН-

Ans:

The structural formulas for the organic products formed in the given reaction are as follows:

ОН
Нас — сН2—он
Нас—сн—сH— CH—CH2—CH2
and
HаС— Cн
CH=CH2
-CH2
-Cн-

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Answer 3

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