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Chapter 22: 29P (page 868)

What organocuprate reagent is needed to convert CH3CH2COCIto each ketone?

a.

b.

c.

Short Answer

Expert verified

Answer

The organocuprate reagents needed to convert CH3CH2COCI to each ketone are shown in the following method:

a.

b.

c.

Step by step solution

01

Step-by-Step Solution Step 1: Use of organocuprate

The organocuprate is used in many nucleophilic substitution reactions to get products such as aldehydes and ketones.

They attack the electrophilic carbon center of any acid chloride structure where chlorine is a powerful leaving group.

02

Choosing the right organocuprate

To obtain the correct organocuprate reagent, you require the retrosynthetic pathway.

The ester and Grignard reagent needed to prepare ketone a. are:

Synthesis of a.

The ester and Grignard reagent needed to prepare ketone b. are:

Synthesis of b.

The ester and Grignard reagent needed to prepare ketone c. are:

Synthesis of c.

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Most popular questions from this chapter

Review the oxidation reactions using Cr+6 reagents in Section 12.12. Then, draw the product formed when compound B is treated with each reagent.

a. NaBH4, CH3OH

b. [1] LiAlH4 ; [2]H2O

c. PCC

d.Ag2O, NH4OH

e. CrO3, H2SO4, H2O

Draw the product formed when the α,β-unsaturated ketone A is treated with each reagent.

(a) NaBH4, CH3OH

(b) H2 (1 equiv), Pd-C

(c) H2 (excess), Pd-C

(d) [1] CH3Li ; [2]H2O

(e) [1] CH3CH2MgBr ; [2]H2O

(f) [1] (CH2=CH2)2; [2]H2O

Question: With reference to the structures of acetylsalicylic acid (aspirin, Chapter 2 opening molecule) and acetaminophen (the active ingredient in Tylenol), explain why acetaminophen tablets can be stored in the medicine cabinet for years, but aspirin slowly decomposes over time.

Question: How do the following experimental results support the resonance description of the relative stability of acid chlorides compared to amides? The C-Cl bond lengths in CH3Cl and CH3COCl are identical (178 pm), but the C-N bond in HCONH2 is shorter than the C-N bond in CH3NH2(135 pm versus 147 pm).

What Grignard reagent and carbonyl compound are needed to prepare each alcohol? As shown in part (d), 3o alcohols with three different R groups on the carbon bonded to the OH group can be prepared by three different Grignard reactions.
See all solutions

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