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Chapter 22: Q34. (page 910)

Question: Draw the products of each reaction

a.

b.

Short Answer

Expert verified

Answer

a.

b.

Step by step solution

01

Step-by-Step Solution Step 1: Addition of Grignard and organolithium reagents to nitriles

Nitriles react with Grignard or organolithium reagent to give ketone via nucleophilic addition.

The mechanism of such a reaction is shown below:

Mechanism

02

Determination of product

Both the given reactions are examples of nitriles reacting with organometallic reagents. The products are given below:

a.

Product of reaction a.

b.

Product of reaction b.

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Most popular questions from this chapter

Question: What products are formed when all of the amide and ester bonds are hydrolyzed in each of the following compounds? Tamiflu [part (a)] is the trade name of the antiviral agent oseltamivir, thought to be the most effective agent in treating influenza. Aspartame [part (b)] is the artificial sweetener used in Equal and many diet beverages. One of the products of this hydrolysis reaction is the amino acid phenylalanine. Infants afflicted with phenylketonuria cannot metabolize this amino acid, so it accumulates, causing mental retardation. When the affliction is identified early, a diet limiting the consumption of phenylalanine (and compounds like aspartame that are converted to it) can make a normal life possible

a.

b.

stereochemistry of the products of reduction depends on the reagent used,as you learned in Sections 20.5 and 20.6. With this in mind, how would you convert3,3-dimethylbutan-2-one [CH3COC(CH3)3] to: (a) racemic 3,3-dimethylbutan-2-ol[CH3CH(OH)C (CH3)3] ;(b) only (R)-3,3-dimethylbutan-2-ol; (c) only (S)-3,3-dimethylbutan-2-ol?

Draw the product formed when pentanal (CH3CH2CH2CH2CHO ) is treated with each reagent. With some reagents, no reaction occurs.

a. NaBH4 , CH3OH

b. {1} LiAlH4 ; {2} H2O

c. H2,Pd-C

d. PCC

e. Na2Cr2O7, H2SO4, H2O

f. Ag2O, NH4OH

g. {1}CH3MgBr ; {2} H2O

h. {1} C6H5Li ; {2} H2O

i. {1} (CH3)2CuLi ; {2} H2O

j.[1]HC≡CNa;[2]H2Ok.[1]CH2C≡CLi;[2]H2O

l. The product in (a) , then TBDMS-Cl , imidazole

Question: Draw the structure corresponding to each name.

  1. 5-methylheptanoyl chloride
  2. isopropyl propanoate
  3. acetic formic anhydride
  4. N-isobutyl-N-methylbutanamide
  5. 3-methylpentanenitrile
  6. o-cyanobenzoic acid
  7. sec-butyl 2-methylhexanoate
  8. N-ethylhexanamide

Draw the products formed (including stereoisomers) when each compound is reduced with NaBH4in CH3OH.
See all solutions

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