Disclaimer The questions contained within this file were given as Exam 1 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 Chapter 18 was also contained on this question The questions covering that material have been removed A Key will be posted Monday March 22 Circle the correct answer for each of the following questions 1 What is the hybridization of the central carbon of CH2 C CH2 a sp b sp2 c sp3 d p 2 Which of the following compounds contains the shortest carbon carbon single bond a CH3 CH3 b CH3 CH CH2 c CH3CH2 CH CH2 d CH2 CH CH CH2 3 The Diels Alder reaction has a no intermediate c two intermediates 4 An allylic cation is a destabilized d resonance stabilized b one intermediate d three intermediates b less stable than a primary carbocation c more stable than a primary carbocation 5 Which of the following compounds undergoes the most rapid free radical bromination reaction 6 In benzene a the p orbitals may not be parallel c some of the p orbitals are parallel b all of the p orbitals are parallel c none of the p orbitals is parallel 7 In an electrophilic aromatic substitution reaction the carbocation intermediate is a not formed c resonance stabilized b destablized d aromatic 8 In electrophilic aromatic substitution reactions the fluorine substituent F is a a p director c an o p director b an o director d a m director 9 Which of the following compounds does not participate in the SN2 reaction 10 Rank the following conjugated polyenes in order of decreasing max 11 Rank the following dienes in order of decreasing stability 12 Rank the following dienophiles in order of decreasing reactivities in Diels Alder reactions with 1 3 cyclohexadiene 13 Rank the following resonance structures in order of their increasing relative importance 14 Rank the following compounds in order of decreasing rates in solvolysis reactions 15 Rank the following compounds in order of increasing rates in electrophilic substitution reactions 16 Rank the following compounds in order of increasing rates in nucleophilic substitution 17 Arrange the following compounds according to increasing rates of their SN1 E1 reactions 18 Which 1 2 addition product is NOT formed in this reaction a a 19 A molecule with multiple resonance structures exists as b b c c d d a one resonance at a time c interconverting resonance structures b a resonance stabilized hybrid d a mixture of multiple species 20 Which product is formed from the following radical reaction 21 vThe following natural product has isoprene units in its structure a 1 b 2 c 3 d 4 22 Which of the following carbanions would you expect to be most stable 23 What is the major product of the following Friedel Crafts acylation NBSBrBrBrBra b c d BrCH3H3CCH3CH3CH3OHa b c d CH3CCl excess AlCl3a b c d OOCH3OCH3H3COH3COOCH3OH3CCH3OOCH3H3COOCH3 24 In electrophilic aromatic substitution reactions a chlorine substituent is a a deactivator and a meta director c an activator and a meta director b a deactivator and an othor para director d an activator and an othor para director 25 What is the major organic product from the following reaction 26 What is the correct organic product from the following reaction The following question require submission of answers on paper 27 Provide the structure of both possible products for the following Diels Alder reaction 28 The polymerization of the following compound is initiated by proton of a strong acid Please proposed a mechanism for the polymerization reaction Show at least two consecutive coupling steps i e the addition of at two monomer reactants to the growing polymer chain Hint Think about the stability of the intermediate 100 oCKMNO4a b c d CH2COOHCH3CH2OHCH2OHCOOHCOOHCOOHCH2CH3OOCH3ClAlCl3OOCH3OOOOOOH3CH3CCH3a b c d CH3H 29 Provide the appropriate steps reagents and intermediate structure s for the following synthetic transformation 30 Provide the structures of A B and C in the following reaction sequence Assuming monomethylation COOHNO2CH3ClAlCl3HNO3H2SO4KMnO4100 oCABC