Disclaimer The questions contained within this file were given as Exam 3 in Spring 2020 These questions are being provided so that you can get a feel for different types of questions that could be asked This is NOT meant to represent the exam that you will be receiving There will be similarities to some questions but it is not a guarantee of exact format Please see the syllabus for more information about our exam A Key will be posted Monday April 26 D sp C sp3 B spd 1 What is the hybridization of the carbonyl oxygen atom of an aldehyde or ketone A sp2 2 The carbonyl oxygen of an aldehyde is A Weakly basic B Strongly basic C May or may not be basic D Not basic at all 3 An aldehyde and ketone that are isomers can be differentiated by A UV vis spectroscopy B Mass spectrometry C Infrared IR spectroscopy D 13C NMR spectroscopy 4 Nucleophilic addition to an aldehyde or ketone is more favorable A If electron donating group s are attached to the C O B If electron0withdrawing group s are near the C O C If bulky group s is are near the C O D If bulky group s is are attached to the C O 5 Give the common or substitutive name s of the major organic product s of the following reaction 6 What is the product of the following reaction 7 Please give the common and or substitutive names for the organic products of the following reaction 8 Please give the substitutive name of the final main organic product of the following reaction Do not include byproducts 9 Give the substitutive name of the following compound 10 Rank the following compounds in order of increasing reactivity in nucleophilic addition A I II III IV B IV III II I C III II I IV D III IV I II 11 Indicate the reagent s needed for the following transformation Provide molecular formulas 12 Indicate the alkyl provide needed for preparing the following Wittig reagent ylide by using the compound name common or systematic or condensed formula PH3P C CH3 2 13 The high boiling points of carboxylic acids are due to A The high polarity of carboxylic acids B The strong hydrogen bonds involving carboxylic acids C The high polarity of the carboxyl group and the formation of hydrogen bonded dimers D The special general structure of carboxylic acids 14 The acidity of a carboxylic acid is enhanced by A Any substituent attached near the carbonyl carbon B An electron donating group attached near the carbonyl carbon C The hydrogen bonding ability of the carboxyl group D An electron withdrawing group attached near the carbonyl carbon 15 Order the following compounds in order of increasing acidity putting the least acidic first as number 1 16 Indicate the product of the following reaction by giving its common or substitutive name 17 Indicate the organic product of the following reaction by giving its common or substitutive name 18 Provide the name or molecular formula of the missing reagent s for the following transformation 19 Give the substitutive name of the following compound 20 The C O stretching of an ester occurs at a much higher frequency than that of an amide because of A The electronegativity of the carboxylate oxygen atom B The polar effect of the carbonyl group C Less effective resonance structures of esters than that of amides D The high polarity of the carboxylate oxygen atom 21 Amides are esters A Less basic than B More basic than C As acidic as D As basic as 22 Nitriles are regarded as carboxylic acid derivatives because A Nitriles are very polar B Nitriles hydrolyze into carboxylic acids C The cyano carbon is electrophilic D The cyano carbon is nucleophilic 23 Typically esters will hydrolyze under conditions than anhydrides A Milder B More diluted C Less dilute D More vigorous 24 What is the first step in the mechanism for the hydrolysis of nitriles in acid A The attack of the CN carbon by a water molecule B The departure of ammonia as the leaving group C The protonation of the CN nitrogen atom D The cleavage of the CN bond 25 The hydrolysis of an ester is faster than the hydrolysis of an amide because i the ester gains less resonance than the amide ii the ester gains more resonance stabilization than the amide iii the transition state of the hydrolysis of an ester involves less polar stabilization iv the transition state of the hydrolysis of an ester involves more polar stabilization A i and iv B iii and iv C ii and iii D i and ii 26 What are the reactants for preparing the following compound under basic conditions C 27 What is the correct sequence for arranging the reactant product and intermediates for the mechanism for the following reaction Electron pushing is indicated by curved arrows A I IV I III C II I IV III 28 What is the organic product of the following reaction B I II III IV D II I IV III A PhCH2COO Na B PhCOO Na C PhCH2COCH3 D PhCOOH 29 What reagent s would be required to achieve the following transformation 30 What is are the principal organic product s of the following reaction The following question require submission of answers on paper 31 Using the curved arrow formalism write down a step by step mechanism for the substitution reaction shown below Please show all steps intermediates electron flow arrows and formal charges 32 Explain why anhydrides are more reactive than amides in nucleophilic acyl substitution reactions 33 Provide an efficient step by step synthesis from the given starting material Use any reagents and compounds in your synthesis More than one step may be required To get full credit you should show all reagents and the products formed in each step of the synthesis mechanisms are not required