CHEM 2312 practice final Version II 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 II on the WebCT course page Your exam will be scored out of 70 and you will get access to the solutions Question 1 What is the ground state electronic configuration of a sodium cation sodium atomic number 11 a 1s22s22p63s1 c 1s22s22p6 Question 9 Which of the following is the most stable conformation of trans 1 ethyl 3 methylcyclohexane b 1s22s22p53s1 d 1s22s22p63s2 Question 2 Which of the following species possesses a formal charge a CCl4 c AlCl4 H3C 1 b SiCl4 d PCl3 2 CH3 CH2CH3 H3C Question 3 Which of the following is a tertiary amine a CH3CH2N CH3 2 c CH3CH2NHCH3 CH2CH3 CH2CH3 CH3 a 1 b CH3 3CNH2 d CH3CH2NHCH CH3 2 CH2CH3 3 4 b 2 c 3 d 4 Question 10 What is the IUPAC name for the following compound Question 4 Which of the following bonds has the smallest dipole moment a C N b C O c C F d O H Question 5 Rank the following in order of decreasing importance as a contributing resonance structure to the molecular structure of acetone CH3COCH3 more important less important O O C C H3C CH3 H3C O 1 C CH3 H3C 2 b 1 3 2 d 3 1 2 b 109 5 c 120 d 180 Question 7 How many constitutional isomers are there with the molecular formula C6H14 b 4 c 5 d 8 Question 8 Which of the following Newman projections represents the most stable conformation of 2 3 dimethylbutane CH3 H H CH3 H H CH3 H CH3 CH3 CH3 H3C CH3 H CH3 1 a 1 2 b 2 b 60 c 120 d 180 Question 12 Which of the following compounds can adopt a chair conformation in which there are no axial methyl groups Question 6 What is the approximate value of the H C H bond angles in a methyl cation CH3 a 3 Question 11 What is the approximate dihedral angle between the two chlorine atoms in the diequatorial conformation of trans 1 2dichlorocyclohexane a 0 CH3 b bicyclo 3 2 1 octane d bicyclo 2 2 1 octane 3 a 1 2 3 c 2 1 3 a 90 a bicyclo 5 4 3 octane c bicyclo 3 2 1 hexane c 3 d 4 CH3 H CH3 H H H3C CH3 CH3 CH3 3 4 a cis 1 2 dimethylcyclohexane b cis 1 3 dimethylcyclohexane c trans 1 3 dimethylcyclohexane d cis 1 4 dimethylcyclohexane Question 13 Which of the following is the definition of a meso compound a A molecule with stereocenters which is chiral b A molecule with stereocenters which is not chiral c A diastereomer with no stereocenters d A chiral compound with more than one stereocenter Question 14 Which of the following statements is not true regarding pairs of enantiomers a They have identical melting points b They have identical boiling points c They rotate plane polarized light in opposite directions d They react at identical rates with chiral reagents Question 21 Which of the following anions is the strongest base Question 15 Which of the following compounds is are chiral a CH3COO c NH2 1 Question 22 What is the IUPAC name of the following compound 3 2 a only 1 c only 2 and 3 b HO d Cl b only 1 and 2 d 1 2 and 3 Question 16 Which of the following Newman projections represents 2R 3R dibromobutane Br Br H CH3 CH3 H3C H3C H H H H 1 a 1 Br Br Br H3C 2 b 2 c 3 Br H H3C CH3 H3C H H Br Br 3 4 d 4 Question 23 What is the hybridization of carbon atoms labeled i iii in the following structure Question 17 Which of the following structures represent the same stereoisomer H Br Br H CH3 CH3 H CH3 H3C OH HO CH3 1 a only 1 and 2 c only 2 and 3 2 H Br 3 b only 1 and 3 d 1 2 and 3 Question 18 How many stereoisomers of 3 bromo 2 butanol CH3CH OH CHBrCH3 exist a 1 c 3 b 2 d 4 Question 19 A solution containing 0 2 g mL of a pure R enantiomer in a 1 dm polarimeter rotates plane polarized light by 2 8 What is the rotation of a solution containing 0 4 g mL of the R isomer in the same polarimeter a 0 7 c 2 8 H2 C i C CH2 ii iii a i sp ii sp iii sp c i sp2 ii sp iii sp2 b i sp2 ii p iii sp2 d i sp2 ii sp2 iii sp2 H CH3 H HO a 1 methylbicyclo 2 2 2 oct 1 ene b 1 methylbicyclo 2 2 2 oct 2 ene c 2 methylbicyclo 2 2 2 oct 1 ene d 2 methylbicyclo 2 2 2 oct 2 ene b 1 4 d 5 6 Question 24 What is the best choice of reagent s to convert 1 pentyne to 2 pentanone a H2O H2SO4 b H2O H2SO4 HgSO4 c BH3 followed by H2O2 NaOH d OsO4 followed by NaHSO3 Question 25 What is are the major organic product s obtained from the following reaction CH3 CH3 H2 Pt CH3 CH3 CH3 CH3 CH3 CH3 Question 20 Which of the following compounds is the strongest acid a CH3COOH c ClCH2COOH b FCH2COOH d BrCH2COOH 1 a only 1 c only 3 2 3 b only 2 d only 2 and 3 Question 26 What is are the major organic product s obtained from the following reaction 1 OsO4 2 NaHSO3 H2O a the rate remains the same b the rate decreases by a factor of 2 c the rate increases by a factor of 2 d the rate increases by a factor of 4 1 2R 3R butanediol 2 2S 3S butanediol 3 meso 2 3 butanediol a only 1 c only 3 b only 2 d only 1 and 2 Question 27 What type of reactive intermediate is formed in the reaction of an alkene with Br2 and water to give a bromohydrin a carbocation c radical Question 32 The reaction of tert butyl bromide CH3 3CBr with methanol in an inert solvent proceeds by an SN1 mechanism to give tertbutyl methyl ether CH3 3COCH3 What is the effect of doubling the concentration of methanol on the rate of the reaction b carbanion d cyclic bromonium ion Question 33 Which of the following sets consists of only polar aprotic solvents a …