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Chapter 10: Q13P (page 516)

Question: Show how you would synthesize the following primary alcohols by adding an appropriate Grignard reagent to formaldehyde.

a.

b.

c.

Short Answer

Expert verified

Answer

a.

b.

c.

Step by step solution

01

Synthesis of alcohol

The primary alcohol is synthesized when the Grignard reagent is added to formaldehyde, but the secondary alcohol is formed when aldehyde other than formaldehyde is added to the Grignard reagent.These reactions take place in the presence of solvents like ether.

02

Synthesis of a primary alcohol in (a)

a. When Grignard reagent ( ) is added to formaldehyde (HCHO) in the presence of ether and the second step with , it results in the formation of primary alcohol.


Synthesis of primary alcohol

03

Synthesis of a primary alcohol in (b)

b. When Grignard reagent ( ) is added to formaldehyde (HCHO) in the presence of ether, and then with , it forms primary alcohol.


Synthesis of primary alcohol

04

Synthesis of primary alcohol in (c)

c. When Grignard reagent ( ) is added to formaldehyde (HCHO) in the presence of ether, and then with H3O+, it forms primary alcohol.


Synthesis of primary alcohol

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Most popular questions from this chapter

Show how you would synthesize the following:

  1. 2-phenylethanol by the addition of formaldehyde to a suitable Grignard reagent
  2. 2-phenylethanol from a suitable alkene
  3. cyclohexylmethanol from an alkyl halide using an SN2 reaction
  4. 3-cyclohexylpropan-1-ol by the addition of ethylene oxide to a suitable Grignard reagent
  5. cis-pent-2-en-1-thiol from a suitable alkenyl halide
  6. 2,5-dimethylhexane from a four-carbon alkyl halide

Give the IUPAC name of the following alcohols.

Question: Which of the._ following compounds are suitable solvents for Grignard -reactions?

a. n-hexane

b. CH3-O-CH3

c. CHCI3

d. Cyclohexane

e. Benzene

f.CH3OCH2CH2OCH3

g.

h

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

In Section 9-7B, we saw how acetylide ions add to carbonyl groups in much the same way as Grignard and organolithium reagents. Acetylide ions also add to ethylene oxide much like Grignard and organolithium reagents. Predict the products obtained by adding the following acetylide ions to ethylene oxide, followed by a dilute acid workup.

a.

b.
See all solutions

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