Under basic conditions, in nucleophilic acyl substitution,Answer A. protonation of...

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Under basic conditions, in nucleophilic acyl substitution,Answer  	 		 			 			A. 			protonation of the carbonyl group is followed by nucleophilic attack. 		 		 			 			B. 			loss of the leaving group is followed by formation of an acylium ion. 		 		 			 			C. 			an SN2 mechanism is followed. 		 		 			 			D. 			the nucleophile must be a weaker base than the leaving group. 		 		 			 			E. 			nucleophilic addition to the carbonyl is followed by loss of a leaving group. 		 	 
	
Document Preview: Homework 8What is the IUPAC name for the following compound? A.propanoic anhydrideB.propanoic propanoic anhydrideC.formyl formateD.butanoic anhydrideE.dipropyl etherUnder basic conditions, in nucleophilic acyl substitution,AnswerA.protonation of the carbonyl group is followed by nucleophilic attack.B.loss of the leaving group is followed by formation of an acylium ion.C.an SN2 mechanism is followed.D.the nucleophile must be a weaker base than the leaving group.E.nucleophilic addition to the carbonyl is followed by loss of a leaving group.What is the major organic product of the following reaction? A.B.C.D.E.Which of the following conditions will drive the equilibrium of the Fischer esterification towards ester formation?AnswerA.addition of waterB.removal of water as it is formedC.addition of alcoholD.both B and CWhich of the following intermediates is present in the acid-catalyzed hydrolysis of t-butyl ethanoate but not in the acid-catalyzed hydrolysis of methyl ethanoate?AnswerA.a protonated carbonylB.a carbocationC.a carbanionD.a carboxylate anionE.1-propanolWhat is the IUPAC name for the following compound? AnswerA.5-chloro-3-methylhexanoneB.1-chloro-1,3-dimethyl-4-pentanoneC.5-chloro-3,5-dimethyl-2-pentanoneD.5-chloro-3-methyl-2-hexanoneE.2-chloro-4-methyl-5-hexanone2 points   Question 7Why do aldehydes undergo nucleophilic addition reactions while esters undergo nucleophilic acyl substitution reactions?AnswerA.The carbonyl carbon of an ester is more electrophilic than that of an aldehyde.B.Aldehydes are more sterically hindered than esters.C.Once the nucleophile adds to an aldehyde, the tetrahedral intermediate is too sterically hindered to eliminate one of the attached groups.D.The ester carbonyl carbon is sp3 hybridized while the aldehyde carbon is sp2 hybridized.E.Once the nucleophile...

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Solution TTs270513_78951_13 
Homework 8 
1. D. butanoic anhydride
An acid anhydride is formed on elimination of a water molecule from two molecules of 
carboxylic acids. 
O
O    H
Butanoic acid
O
HO
Butanoic acid
O
O
O
Butanoic anhydride
+ H2O

2. E. Nucleophilic addition to the carbonyl is followed by loss of a leaving group.
R
C
O
Y Nu
R C
O
Y
Nu
R
C
O
Nu
+ Y
Nucleophilic attack tetrahedral intermediate
expulsion of
leaving group
 
 
3. E. 
Mechanism:

Under basic conditions, in nucleophilic acyl substitution, Answer A. protonation of the carbonyl group is followed by nucleophilic attack. B. loss of the leaving group is followed by formation of an...

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A.	protonation of the carbonyl group is followed by nucleophilic attack.
B.	loss of the leaving group is followed by formation of an acylium ion.
C.	an SN2 mechanism is followed.
D.	the nucleophile must be a weaker base than the leaving group.
E.	nucleophilic addition to the carbonyl is followed by loss of a leaving group.