VCU CHEM301 Su21 Midterm #1 CHEM-301-002-SU2021 - ORGANIC CHEMISTRY I

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VCU CHEM301 Su21 Midterm #1 Due Jun 27 at 11:59pm Points 115.17 Questions 33 Available Jun 25 at 6pm - Jun 29 at 11:59pm 4 days Time Limit 75 Minutes Instructions This quiz was locked Jun 29 at 11:59pm. Attempt History Attempt Time Score LATEST Attempt 1 73 minutes 69.8 out of 115.17 Score for this quiz: 69.8 out of 115.17 Submitted Jun 27 at 11:38pm This attempt took 73 minutes. The Chemistry Department supports the VCU HONOR SYSTEM and operates within its guidelines. The Honor System must be upheld and enforced by each member of the Virginia Commonwealth University community. The fundamental attributes of our community are honor and integrity. By taking this exam, you are agreeing to abide by the full VCU Honor Policy. You may NOT have help of any kind on this exam. All work submitted, must be your own. You may NOT give any help to another student on this exam. You are NOT allowed to use your notes, Lecture Slides, textbook, or similar material. You are NOT allowed to use any online resource. You are allowed to use a calculator that DOES NOT connect to Wi-Fi, cellular, etc. and scrap paper as needed. 3.49 / 3.49 pts Question 1 The compound methylamine, CH NH , contains a C-N bond. In this 3 2 VCU CHEM301 Su21 Midterm #1: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/91089 1 of 23 7/4/2021, 22:16
bond, which of the following best describes the charge on the carbon atom? partial positive charge Correct! Correct! 3.49 / 3.49 pts Question 2 Which of the following are acceptable Lewis structures, including formal charges, for nitric acid, HNO ? 3 B only Correct! Correct! VCU CHEM301 Su21 Midterm #1: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/91089 2 of 23 7/4/2021, 22:16
3.49 / 3.49 pts Question 3 Which of the following bonding patterns of carbon is not allowed in the formation of an organic compound? F Correct! Correct! 3.49 / 3.49 pts Question 4 Which of the following structures (a-d) is another resonance structure of VCU CHEM301 Su21 Midterm #1: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/91089 3 of 23 7/4/2021, 22:16
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the following organic molecule? B Correct! Correct! 0 / 3.49 pts Question 5 Which of the following choices represent(s) a pair of resonance forms? VCU CHEM301 Su21 Midterm #1: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/91089 4 of 23 7/4/2021, 22:16
C ou Answered ou Answered both B and C orrect Answer orrect Answer 3.49 / 3.49 pts Question 6 Which of the following condensed formulas represents the same compound as the line-angle structure shown? VCU CHEM301 Su21 Midterm #1: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/91089 5 of 23 7/4/2021, 22:16
CH CH OCH N(CH CH ) Correct! Correct! 3 2 2 2 3 2 0 / 3.49 pts Question 7 When methanol (CH OH) acts as a base, its conjugate acid is ________. 3 CH O ou Answered ou Answered 3 CH OH orrect Answer orrect Answer 3 2 + VCU CHEM301 Su21 Midterm #1: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/91089 6 of 23 7/4/2021, 22:16
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3.49 / 3.49 pts Question 8 Which of the following pairs of bases lists the stronger base first? H N > CH COO Correct! Correct! 2 3 3.49 / 3.49 pts Question 9 Which proton is the most acidic in the compound below? 2 Correct! Correct! VCU CHEM301 Su21 Midterm #1: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/91089 7 of 23 7/4/2021, 22:16
0 / 3.49 pts Question 10 How many carbon-carbon σ bonds are present in the molecule shown? 3 ou Answered ou Answered 5 orrect Answer orrect Answer 3.49 / 3.49 pts Question 11 Which of the following statements about π bonds is/are correct? VCU CHEM301 Su21 Midterm #1: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/91089 8 of 23 7/4/2021, 22:16
Most of the electron density in a π bond is centered above and below the internuclear axis. Correct! Correct! 0 / 3.49 pts Question 12 Based on the structure below, what is the value for the H-N-CH bond angle? 3 120 degrees orrect Answer orrect Answer 109 degrees ou Answered ou Answered 0 / 3.49 pts Question 13 VCU CHEM301 Su21 Midterm #1: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/91089 9 of 23 7/4/2021, 22:16
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In the structure below, the hybridization of the oxygen is ________ and the C-O-C bond angle is ________. sp ; <109.5° orrect Answer orrect Answer 3 sp; 120° ou Answered ou Answered 3.49 / 3.49 pts Question 14 Shown below is one of the sex pheremones from the butterfly family. How many sp hybridized carbon atoms are present in this molecule? 2 VCU CHEM301 Su21 Midterm #1: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/91089 10 of 23 7/4/2021, 22:16
5 Correct! Correct! 0 / 3.49 pts Question 15 Triethylamine [(CH CH ) N] is a molecule in which the nitrogen atom is ________ hybridized and the C-N-C bond angle is ________. HINT: Draw this compound... 3 2 3 sp ; <109.5° orrect Answer orrect Answer 3 sp ; >109.5° ou Answered ou Answered 2 3.49 / 3.49 pts Question 16 Which of the labeled atoms in the following structure are sp hybridized? 2 VCU CHEM301 Su21 Midterm #1: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/91089 11 of 23 7/4/2021, 22:16
2 & 3 Correct! Correct! 3.49 / 3.49 pts Question 17 Which one of the molecules shown below has a net molecular dipole moment? CH CCl Correct! Correct! 3 3 VCU CHEM301 Su21 Midterm #1: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/91089 12 of 23 7/4/2021, 22:16
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3.49 / 3.49 pts Question 18 What intermolecular forces are present among molecules in dimethyl ether, CH OCH ? 3 3 both London dispersion forces and dipole-dipole forces Correct! Correct! 0 / 3.49 pts Question 19 Which of the following functional groups is not present in the HIV protease inhibitor drug called Saquinavir, shown below? VCU CHEM301 Su21 Midterm #1: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/91089 13 of 23 7/4/2021, 22:16
amine ou Answered ou Answered ketone orrect Answer orrect Answer 0 / 3.49 pts Question 20 Rank the following compounds in order of acidity (strongest acid to weakest acid). I>III>IV>II orrect Answer orrect Answer II>IV>III>I ou Answered ou Answered VCU CHEM301 Su21 Midterm #1: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/91089 14 of 23 7/4/2021, 22:16
3.49 / 3.49 pts Question 21 How many secondary (2°) carbons are found in 5-ethyl-3,3,4- trimethylheptane? HINT: Draw out this compound, it will be MUCH easier to solve. 3 Correct! Correct! 3.49 / 3.49 pts Question 22 Consider the three isomeric alkanes n -hexane, 2,3-dimethylbutane, and 2-methylpentane. Which of the following correctly lists these compounds in order of increasing boiling point (lowest boiling point to highest)? HINT: Draw out these three compounds, it will be MUCH easier to solve. VCU CHEM301 Su21 Midterm #1: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/91089 15 of 23 7/4/2021, 22:16
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2,3-dimethylbutane < 2-methylpentane < n -hexane Correct! Correct! 0 / 3.49 pts Question 23 The structures below are ________. structural isomers orrect Answer orrect Answer not isomers ou Answered ou Answered 3.49 / 3.49 pts Question 24 Which of the following statements concerning the C -C 2 3 VCU CHEM301 Su21 Midterm #1: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/91089 16 of 23 7/4/2021, 22:16
conformers (rotation around the C -C bond) of butane is true? 2 3 The gauche and anti conformers differ primarily in the amount of steric strain present. Correct! Correct! 0 / 3.49 pts Question 25 Identify the correct IUPAC name for the structure shown below. HINT: This is a little tricky... 1- tert -butyl-2-chloro-5-bromocycloheptane ou Answered ou Answered VCU CHEM301 Su21 Midterm #1: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/91089 17 of 23 7/4/2021, 22:16
5-bromo-1- tert -butyl-2-chlorocycloheptane orrect Answer orrect Answer 3.49 / 3.49 pts Question 26 Which of the following correctly ranks the cycloalkanes (cyclobutane, cyclohexane, cyclopentane, and cyclopropane) in order of increasing (lowest to highest) ring strain? HINT: Draw out these four compounds... cyclohexane < cyclopentane < cyclobutane < cyclopropane Correct! Correct! 0 / 3.49 pts Question 27 In the lowest energy chair conformation of cis -1,3-dimethylcyclohexane, how many axial positions are occupied by hydrogen atoms? VCU CHEM301 Su21 Midterm #1: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/91089 18 of 23 7/4/2021, 22:16
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HINT: To start, draw the chair conformations of cis-1,3- dimethylcyclohexane... 6 orrect Answer orrect Answer 3 ou Answered ou Answered 0 / 3.49 pts Question 28 Which of the statements below correctly describes the chair conformations of trans -1,4-dimethylcyclohexane? HINT: To start, draw the chair conformations of trans-1,4- dimethylcyclohexane... The two chair conformations are of equal energy. ou Answered ou Answered VCU CHEM301 Su21 Midterm #1: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/91089 19 of 23 7/4/2021, 22:16
The higher energy chair conformation contains two axial methyl groups. orrect Answer orrect Answer 0 / 3.49 pts Question 29 Which of the statements below correctly describes the chair conformations of trans -1,3-diethylcyclohexane? HINT: To start, draw the chair conformations of trans-1,3- diethylcyclohexane... The lower energy chair conformation contains two equatorial ethyl groups. ou Answered ou Answered The two chair conformations are equal in energy. orrect Answer orrect Answer 3.49 / 3.49 pts Question 30 In the lowest energy conformation of the compound below, how many alkyl substituents are equatorial? VCU CHEM301 Su21 Midterm #1: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/91089 20 of 23 7/4/2021, 22:16
HINT: To start, draw the chair conformations of this compound... 2 Correct! Correct! 3.49 / 3.49 pts Question 31 In the lowest energy conformation of the compound below, how many alkyl substituents are axial? HINT: To start, draw the chair conformations of this compound... 0 Correct! Correct! VCU CHEM301 Su21 Midterm #1: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/91089 21 of 23 7/4/2021, 22:16
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3.49 / 3.49 pts Question 32 Arrange the following Newman projections of butane in order of energy (lowest to highest). I < III < II < IV Correct! Correct! 3.49 / 3.49 pts Question 33 Which line-angle formula corresponds to the chair conformation shown VCU CHEM301 Su21 Midterm #1: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/91089 22 of 23 7/4/2021, 22:16
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below? III Correct! Correct! Quiz Score: 69.8 out of 115.17 VCU CHEM301 Su21 Midterm #1: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/91089 23 of 23 7/4/2021, 22:16
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