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) HC≡C:^–
(b) CH₃CH₂–C≡C:^–

Show how to make these deuterium-labeled compounds, using CD₃MgBr and D₂O as your sources of deuterium, and any non-deuterated starting materials you wish.

d. Ph(CD₃)₂COD

Show how to make these deuterium-labeled compounds, using CD₃MgBr and D₂O as your sources of deuterium, and any non-deuterated starting materials you wish.

b. CH₃C(OH)(CD₃)₂

Show how to make these deuterium-labeled compounds, using CD₃MgBr and D₂O as your sources of deuterium, and any non-deuterated starting materials you wish.

a. CH₃CH(OD)CD₃

Show how you would synthesize the following:

a. 2-phenylethanol by the addition of formaldehyde to a suitable Grignard reagent

Show how you would synthesize the following alcohol by adding Grignard reagents to ethylene oxide.

(a) 2-phenylethanol

Show how you would add Grignard reagent to acid chloride or ester to synthesize the following alcohols.

a. Ph₃C–OH

Show how you would synthesize following tertiary alcohol by adding an appropriate Grignard reagent to a ketone.

b. Ph₃COH

Show two ways you could synthesize each of the following secondary alcohol by adding an appropriate Grignard reagent to an aldehyde.

(a)