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Chapter 10: Q11P (page 513)

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

Short Answer

Expert verified

The suitable solvents for Grignard reagents the correct options are (b)

, CH3-O-CH3(f) CH3OCH2CH2OCH3,g.and h

Step by step solution

01

Grignard reactions

A Grignard reaction uses Mg metal with alkyl halides in the presence of a suitable solvent such as ether. When we take aldehyde and ketone compounds, Grignard reagents act as nucleophiles.

02

Suitable solvents for Grignard reactions

The Grignard reaction occurs in a solvent that contains an ether functional group. In the given solvents, (b), (f), (g), and (h) are possible solvents because they contain an ether (R-O-R) functional group. In the case of dimethyl ether(b), it needs to be liquefied first at low temperature to use as a solvent because it is in gaseous form at room temperature.

  1. So, the correct options are (b)CH3-O-CH3

, (f)CH3OCH2CH2OCH3,

(g)

and h

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Most popular questions from this chapter

Compound A (C7H11Br) is treated with magnesium in ether to give B (C7H11MgBr) , which reacts violently with D2O to give 1-methylcyclohexene with a deuterium atom on the methyl group (C). Reaction of B with acetone (CH3COCH3) followed by hydrolysis gives D(C10H18O). Heating D with concentrated H2SO4 gives E (C10H16) , which decolorizes two equivalents of Br2 to give F(C10H16Br4) . E undergoes hydrogenation with excess H2 and a Pt catalyst to give isobutylcyclohexane. Determine the structures of compounds A through F, and show your reasoning throughout.

Devise a synthesis for each compound, starting with methylenecyclohexane and any other reagents you need.

(a) 1-methylcyclohexanol (b) cyclohexylmethanol

(c) 1-(hydroxymethyl)cyclohexanol (d) trans-2-methylcyclohexanol

(e) 2-chloro-1-methylcyclohexanol (f) 1-(phenylmethyl)cyclohexanol

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

Compare the properties of propan-2-ol (I) and the hexafluoro analog II

(I) mol. wt. 60 g/mole boiling point 82 °C

dipole moment 1.66 D

pKa16.5

(II)mol. wt. 168 g/mole boiling point 58 °C

dipole moment 0.32 D

pKa9.3

(a) Compound II has almost triple the molecular weight of I, but II has a lower boiling point. Explain.

(b) Explain why the dipole moment of Compound II is much lower than the dipole moment of I, despite the presence of the six electronegative fluorine atoms.

(c) Why is II a stronger acid than I?

Grignard reagents react slowly with oxetane to produce primary alcohols. Propose a mechanism for this reaction, and suggest why oxetane reacts with Grignard reagents even though most ethers do not.
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