CHEM 2312 practice final Version I The following standardized final examination covers the entire introductory year of organic chemistry CHEM 2311 and 2312 at Georgia Tech The exam consists of 70 multiple choice questions each with four choices for the correct answer There is a single correct answer to each question To most effectively use this as a guide to the final complete the examination in a single uninterrupted two hour session without reference to other materials lock your door turn off your phone and switch off your computer Then enter your answers into T square there is a link to Practice Final I on the WebCT course page Your exam will be scored out of 70 and you will get access to the solutions Question 1 Question 1 What is the ground state electronic configuration of an oxygen atom oxygen atomic number 8 a 1s22s12p5 b 1s22s22p4 1 1 6 c 1s 2s 2p d 1s22s22p2 Question 8 Which of the following is the most stable conformation of cis1 isopropyl 3 methylcyclohexane CH CH 3 2 CH CH 3 2 CH 3 H3C 1 Question 2 Which of the following is a tertiary alcohol a CH3CH2OCH3 b CH3 3COH c CH3 2CHOH d CH3CH2CH2OH CH 3 CH CH 3 2 3 a 1 Question 4 Which atomic orbitals overlap to form the carbon carbon molecular bonding orbital of ethyne HC CH a C2p C2p b Csp Csp c Csp2 Csp2 d Csp3 Csp3 Question 5 Which of the following compounds has only 1 and 3 carbon atoms a hexane b 2 methylpentane c 3 methylpentane d 2 3 dimethylbutane Question 6 Which of the following Newman projections does not represent 2 methylhexane CH3 H H H CH3 CH2CH2CH3 H 1 a 1 CH CH3 2 H H CH2CH3 2 b 2 H3 C H CH2CH3 H H CH2CH3 3 c 3 H H CH2CH2CH2CH3 H H CH3 4 b 2 c 3 d 4 Question 9 Which of the following alkanes has the highest boiling point a 2 3 dimethylbutane b 2 methylpentane c 3 methylpentane d hexane Question 10 Which of the following statements is not true regarding the conformation of substituted cyclohexanes a ring inversion of cyclohexanes between two chair conformations takes place via a boat conformation b substituted cyclohexanes are destabilized by 1 3 diaxial interactions c the boat conformation of cyclohexane is more stable than the chair conformation d the relative amount of two conformations of substituted cyclohexanes can be determined from the difference in strain energy Question 11 What is the approximate dihedral angle between the two chlorine atoms in the diaxial conformation of trans 1 2dichlorocyclohexane a 0 b 60 c 120 d 180 Question 12 Which of the following undergoes the most exothermic combustion per carbon atom a cyclopropane b cyclobutane c cyclohexane d cycloheptane 4 d 4 Question7 What is the IUPAC name for the following compound a cycloheptane c bicyclo 5 4 heptane CH CH 3 2 H 3C Question 3 Which of the following statements is not true regarding resonance structures a All resonance structures must have the same number of electrons b Each atom in all of the resonance structures must have a complete shell of valence electrons c All resonance structures must have the same arrangement of atoms d All resonance structures must be valid Lewis structures H 2 b bicyclo 3 2 0 heptane d cyclobutylcyclopentane Question 13 Which of the following is the definition of a pair of enantiomers a A pair of structures that are superposable mirror images of one another b A pair of stereoisomers that are non superposable mirror images of one another c A pair of stereoisomers that are not mirror images of one another d A pair of stereoisomers that have equal specific rotations Question 14 Which of the following statements is true a All mirror images are enantiomers b All molecules that have stereocenter centers are chiral c Isomers that are not superposable on their mirror images are enantiomers d Superposable structural isomers are enantiomers Question 15 Which of the following have the S configuration H CH3 OH CH CH3 H 1 H3C H CH2 CH CH3 2 3 2 a only 1 c only 1 and 2 b only 2 d 1 2 and 3 Question 16 Which of the following Newman projections represents meso2 3 dibromobutane Br Br H Br Br Br H3C H3C CH3 H3C CH3 H H Br H H3C CH3 H3C H H H H Br Br 1 2 3 4 a 1 b 2 c 3 Question 20 A solution containing 0 2 g mL of a pure R enantiomer in a 1 dm polarimeter rotates plane polarized light by 3 What is the specific rotation of the R isomer a 0 017 b 0 6 c 0 6 d 15 CH2CH3 CH2CH3 CH3CH2 Question 19 How much of the R enantiomer is present in 10 g of a mixture which has an enantiomeric excess of 60 of the R isomer a 2 g b 4 g c 6 g d 8 g d 4 Question 21 Which of the following is the correct order of decreasing basicity stronger base weaker base a NH3 MeNH2 H2O HF b MeNH2 NH3 MeOH CH4 c NH3 Me3N H2O MeOH d CH3COONa NaOH NaOMe NaNMe2 Question 22 Which of the following terms describes the reactivity of boron tribromide BBr3 a Br nsted Lowry acid and Lewis acid b Br nsted Lowry base and Lewis base c Lewis acid and not a Br nsted Lowry acid d Lewis base and not a Br nsted Lowry base Question 23 What is the IUPAC name of the following compound Question 17 Which of the following structures represent the same stereoisomer H Cl CH 3 H H H 3C Cl CH 3 Cl CH 3 1 a only 1 and 2 c only 2 and 3 Cl H Cl H CH 3 H Cl 2 a bicyclo 6 2 oct 2 ene c bicyclo 2 2 2 2 octene b bicyclo 4 4 4 oct 2 ene d bicyclo 2 2 2 octene CH 3 3 b only 1 and 3 d 1 2 and 3 Question 24 What is the major organic product obtained from the following reaction 1 BH3 2 H2O2 Question 18 How many stereoisomers of 2 chloro 3 methylbutane CH3 2CHCHClCH3 exist a 1 b 2 c 3 d 4 NaOH HO OH OH 1 a 1 b 2 OH 2 c 3 3 d 4 4 Question 25 What is the major organic product obtained from the following reaction CH3 Br Br CH3 CH3 OH OH Br2 H2 O 1 HO 2 HO CH3 3 a 1 b 2 Br Cl 4 c 3 d 4 Question 26 What type of reactive intermediate is formed in the reaction of an alkene with HBr to give a bromoalkane a carbocation b carbanion c radical d cyclic bromonium ion Question 27 What is are the major organic product s obtained from the following reaction B r2 1 2R 3R dibromobutane 2 2S 3S bibromobutane 3 meso 2 3 dibromobutane a only 1 c only 3 a bromination …