Organic Chemistry

Section 18.4 Reactions of Carbonyl Compounds with Carbon Nucleophiles 741 substituents come from the Grignard reagent. Alcohols ...

Compared with other carbon nucleophiles, cyanide ion is a relatively weak base (the of is 9.14, the of is 25, the of is 50), whi ...

SOLUTION TO 13a The starting material for the synthesis of the two-carbon com- pound must be formaldehyde. Addition of hydrogen ...

diisobutylaluminum hydride DIBALH CH 3 CHCH 2 Al CH 2 CHCH 3 CH 3 H CH 3 744 CHAPTER 18 Carbonyl Compounds II Esters undergo two ...

Section 18.5 Reactions of Carbonyl Compounds with Hydride Ion 745 The reaction is carried out at (the temperature of a dry ice–a ...

746 CHAPTER 18 Carbonyl Compounds II of the amide. Overall, the reaction converts a carbonyl group into a methylene group. (Noti ...

Section 18.6 Reactions of Aldehydes and Ketones with Nitrogen Nucleophiles 747 18.6 Reactions of Aldehydes and Ketones with Nitr ...

748 CHAPTER 18 Carbonyl Compounds II represents any species in the solution that is capable of donating a proton, and represents ...

1.5 1.0 0.5 1 pH kobsd (min −^1 ) 234567 Figure 18.2 Dependence of the rate of the reaction of acetone with hydroxylamine on th ...

750 CHAPTER 18 Carbonyl Compounds II The mechanism for enamine formation is exactly the same as that for imine forma- tion, unti ...

Section 18.6 Reactions of Aldehydes and Ketones with Nitrogen Nucleophiles 751 3-D Molecules: The N-methylimine of acetone; The ...

752 CHAPTER 18 Carbonyl Compounds II NONSPECTROPHOTOMETRIC IDENTIFICATION OF ALDEHYDES AND KETONES Before spectrophotometric tec ...

PROBLEM 23 Hydration of an aldehyde can also be catalyzed by hydroxide ion. Propose a mechanism for hydroxide-ion-catalyzed hydr ...

754 CHAPTER 18 Carbonyl Compounds II The extent to which an aldehyde or a ketone is hydrated in an aqueous solution de- pends on ...

Section 18.7 Reactions of Aldehydes and Ketones with Oxygen Nucleophiles 755 PRESERVING BIOLOGICAL SPECIMENS A 37% solution of f ...

756 CHAPTER 18 Carbonyl Compounds II When the carbonyl compound is a ketone instead of an aldehyde, the addition products are ca ...

PROBLEM 26 Show the mechanism for the acid-catalyzed hydrolysis of an acetal. PROBLEM 27 Explain mechanistically why an acetal o ...

758 CHAPTER 18 Carbonyl Compounds II PROBLEM 28 a. Would you expect hemiacetals to be stable in basic solutions? Explain your a ...

Section 18.8 Protecting Groups 759 PROBLEM 29 a. What would have been the product of the preceding reaction with if the keto gro ...

760 CHAPTER 18 Carbonyl Compounds II An amino group can be protected by being converted into an amide (Section 17.8). The acetyl ...