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Chapter 10: Q16P (page 519)

Propose a mechanism for the reaction of acetyl chloride with phenylmagnesium bromide to give 1,1-diphenylethanol.

Short Answer

Expert verified

When acid chloride is added to 2 equivalents of Grignard reagent in an ether solvent, and after protonation, it forms tertiary alcohol. In acid chlorides, the OH group of the acid is replaced by a Cl atom.

Step by step solution

01

Addition of acid chloride to Grignard reagent

When acid chloride is added to 2 equivalents of Grignard reagent in an ether solvent, and after protonation, it forms tertiary alcohol. In acid chlorides, the OH group of the acid is replaced by a Cl atom.

02

Mechanism for the reaction between an acid chloride and phenylmagnesium bromide

The mechanism shows the nucleophilic substitution, and Cl is the leaving group. It takes place at carbonyl carbon, which is the unusual feature we see in this mechanism.

Mechanism of reaction between an acid chloride and Grignard reagent

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Most popular questions from this chapter

Describes a new method to perform ozonolysis reactions that used pyridine (py) to generate the final aldehydes and ketones in a non-aqueous reaction medium. In a subsequent publication (J. Org. Chem., 2013, 78, 42), Professor Dussault (U. of Nebraska at Lincoln) described a “tandem” process in which two reactions are performed sequentially without having to isolate the intermediate aldehyde or ketone. Show the final product from each sequence. (Hint: The isolated products were from the larger part of the structure. Ignore stereochemistry.)

A formate ester, such as ethyl formate, reacts with an excess of a Grignard reagent to give (after protonation) secondary alcohols with two identical alkyl groups.

a. Propose a mechanism to show how the reaction of ethyl formate with an excess of allylmagnesium bromide gives, after protonation, hepta-1,6-dien-4-ol.


b. Show how you would use reactions of Grignard reagents with ethyl formate to synthesize the following secondary alcohols.

i. pentan-3-ol

ii. diphenylmethanol

iii. trans, trans-nona-2,7-dien-5-ol

Draw the structures of the following compounds. (Includes both new and old names.)

(a) diphenylmethanol

(b) 3-(chloromethyl)heptan-3-ol

(c) 3-cyclohexen-1-ol

(d) 3-cyclopentylhexan-2-ol

(e) meso-3,5-heptanediol

(f) cyclohexene glycol

(g) 3-(bromomethyl)phenol

(h) (2R,3R)-2,3-pentanediol

(i) cyclohex-3-ene-1-thiol

(j) diethyl disulfide

(k) 2-methylhex-4-yn-2-ol

Question: Give both the IUPAC name and the common name for each alcohol.

(a)

(b)

(c)

(d)

Show how you would accomplish the following transformations. You may use any additional reagents you need.
See all solutions

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