Ch16 - 320 S olutions C hapter 15: O rganometallic...

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321 CI-i:J (c) Solutions CHAPTER 16 Solutions to the Problems Chapter 16: Aldehydes and Ketones frillliem 16.1 Write the IUPAC names for each compound. Specify the configuration in (c). -3,3:Dimethylbutanal 1,3-Cyclohexanedione (R)-2.Phenylpropanal ,Eroblem 16.2 Write structural formu1a~ for all aldenydes with the molecular formula C 6 H l2 0 and give each its IUPAC name. Which of these aldehydes are dural? . o 0 " " CH3-CH2-CH2-CH2-CH2-CH CH 3 -?H-CH 2 -CH 2 -CH CH 3 Hexanal 4-Methylpentanal Chapter 15: Organometallic Compounds 1. Me 2 CuLi Ether -78°C to . .40°C 2. H 2 0, HCI Solutions (racemic) 320 Once again, the starting material is a single enantiomer (S,S),the stereochemistry of which determines the stereochemistry of the sing~eenantiomerproduct. Problem 15.24 Gilman reagents are versatile reagents for making new carbon-carbon bonds. Complete the follQwing reacti use Gilman reagents. (a) M~CuLi Ether Leaving . .. group ~ (racemic) Me2CuLi (b) Ether -78°C to -40°C W -S-CF .' II . 3 o Leaving group In either case, the Gilman reagent is reacting with the leaving group, either the iodo atom, or trifluoromethyl sulll (triflate) group, to give a new carbon-carbon bond. o o CH -CH -CH-CH * 2 -CH CH -CH-CH " 3 2 I 3 2 2 I " CH 3 CH 3 3·Methylpentanal 2-Methylpentanal (chiral) (chiral) o CH 0 J 3 II CH -CH-CH-CH CH 3 -C-CH 2 3 I I " I . CH 3 CH 3 CH 3 2,3-Dimethylbutanal 3,3-Dimethylbutanal (chiral) Problem 16.3 Write the IUPAC name for each compound. o (b) . O (X (a) HO OH ~ a 1,3-Dihydroxy-2-propanone 1,2-Cyclohexanedione Problem 16.4 Show how these four products can be synthesized from the same Grignard reagent. V OH ~OH (c) (.loA (d) (b) V (racemic) (racemic) (racemic) (racemic) All of the products can be obtained using 3-cyclohexenylmagnesium bromide and the other reactants shown. Note that in each case at least one chiral center is produced so that racemic mixtures will be generated in the reactions. o CH 3 2 I " CH 2 I CH 3 2-EthylbutanaI CH 0 I 3" CH '-C-CH 3" 2 I CH 3 2,2-Dimethylbutanal (c) 4-Aminobutanal
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~OH ai There are two combi~ations of Wittig reagent and carbonyl compound that could be used to make this alke~e. There are also two combinations of Wittig reagent and carboriyl compound that could be used to make this alkyl halide is used in the SN2 reaction with PPh;3' 322 Solutions 16 ' Aldehydes and Ketones Solutions 323 Chapter . The other involves the Wittig reagent prepared from bromomethane w CHp-t 2. HCI +-0==0 '~ 1. PPI1J - + ~e-PPh3 ~O ... '+D=~ CH:!Br 2. BuLi W 1. HOi The second synthesis is better because the more reactive CH 3 Br is used in the SN2 r'eaction with PPh3· _2_. H_C_'_. .. ~O V In the above examples, illkyl bromides were used. In fact, alkyl chlorides and iodides could have also been 00 utilized. 1. oblem 16.6 Hydrolysis of an acetal in aqueous acid gives an aldehyde or k~tone and two molecule~ of alcohol or one 1~2.HCI ~Iecule of a diol. Draw the structural formulas for the products of hydrolysIs of each 111 aqueous aCId.
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This note was uploaded on 07/09/2011 for the course CHE 301 taught by Professor Diver during the Spring '08 term at SUNY Buffalo.

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Ch16 - 320 S olutions C hapter 15: O rganometallic...

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