VCU CHEM301 Su21 Midterm #3 CHEM-301-002-SU2021 - ORGANIC CHEMISTRY I

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VCU CHEM301 Su21 Midterm #3 Due Jul 11 at 11:59pm Points 115.17 Questions 33 Available after Jul 9 at 6pm Time Limit 75 Minutes Instructions Attempt History Attempt Time Score LATEST Attempt 1 74 minutes 59.33 out of 115.17 Score for this quiz: 59.33 out of 115.17 Submitted Jul 11 at 2:12am This attempt took 74 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 models, including pre-made models. 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 What is the IUPAC name of the compound shown below? VCU CHEM301 Su21 Midterm #3: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/92107 1 of 22 7/13/2021, 22:40
HINT: This one is a little tricky... ( 1R,3S )-1,3-dichloro-1-ethyl-3-methylcyclopentane Correct! Correct! 0 / 3.49 pts Question 2 Which of the following compounds will undergo an S 2 reaction most readily? N (CH ) CCH I ou Answered ou Answered 3 3 2 VCU CHEM301 Su21 Midterm #3: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/92107 2 of 22 7/13/2021, 22:40
(CH ) CHCH CH CH I orrect Answer orrect Answer 3 2 2 2 3.49 / 3.49 pts Question 3 Which of the compounds below undergoes solvolysis in aqueous ethanol most rapidly? 3-iodo-3-methylpentane Correct! Correct! 3.49 / 3.49 pts Question 4 Which of the following alkyl halides reacts most rapidly via an S 2 reaction with NaCN? N 1-iodohexane Correct! Correct! VCU CHEM301 Su21 Midterm #3: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/92107 3 of 22 7/13/2021, 22:40
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0 / 3.49 pts Question 5 Rank the following molecules in order of increasing relative rate of S 1 solvolysis with methanol and heat (slowest to fastest reacting). N 2 < 3 < 4 < 1 < 5 orrect Answer orrect Answer 2 < 3 < 4 < 5 < 1 ou Answered ou Answered 0 / 3.49 pts Question 6 VCU CHEM301 Su21 Midterm #3: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/92107 4 of 22 7/13/2021, 22:40
When trans -1-iodo-4-methylcyclohexane is heated in methanol, the product mixture is primarily ________. a mixture of diasteromeric ethers orrect Answer orrect Answer a mixture of diasteromeric alcohols ou Answered ou Answered 0 / 3.49 pts Question 7 Which of the cations below would be subject to a structural rearrangement? 3 orrect Answer orrect Answer 2 and 3 ou Answered ou Answered VCU CHEM301 Su21 Midterm #3: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/92107 5 of 22 7/13/2021, 22:40
0 / 3.49 pts Question 8 Which of the following alkyl halides is most likely to undergo rearrangement in an S 1 reaction? N 2-chloro-3,3-dimethylpentane orrect Answer orrect Answer 1-bromo-4-methylcyclohexane ou Answered ou Answered 3.49 / 3.49 pts Question 9 Which of the following alkyl chlorides is least likely to undergo rearrangement during a solvolysis reaction? 2-chloro-2-methylpentane Correct! Correct! VCU CHEM301 Su21 Midterm #3: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/92107 6 of 22 7/13/2021, 22:40
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3.49 / 3.49 pts Question 10 Which of the following carbocations is likely to undergo a hydride shift? II and IV Correct! Correct! 3.49 / 3.49 pts Question 11 Rank the following compounds in order of increasing reactivity in an S 2 reaction. (Fastest is first, slowest is last.) N VCU CHEM301 Su21 Midterm #3: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/92107 7 of 22 7/13/2021, 22:40
IV > II > I > III Correct! Correct! 0 / 3.49 pts Question 12 Consider the substitution reaction shown below. By what mechanism will the reaction proceed? S 1 ou Answered ou Answered N S 2 orrect Answer orrect Answer N 0 / 3.49 pts Question 13 Dehydration of 1-butanol with concentrated sulfuric acid at 140 C results in the formation of mainly trans -2-butene. According to these results, which of the following conclusions might be valid? VCU CHEM301 Su21 Midterm #3: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/92107 8 of 22 7/13/2021, 22:40
The reaction undergoes an E2-type elimination mechanism. ou Answered ou Answered The reaction undergoes an E1-type elimination mechanism in conjunction with a hydride shift. orrect Answer orrect Answer 0 / 3.49 pts Question 14 How many distinct alkene products are possible, including stereoisomers, when the alkyl iodide below undergoes E2 elimination? 2 ou Answered ou Answered 5 orrect Answer orrect Answer VCU CHEM301 Su21 Midterm #3: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/92107 9 of 22 7/13/2021, 22:40
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0 / 3.49 pts Question 15 Which of the following alkyl halides can produce only a single alkene product from when treated with sodium methoxide? 3-chloro-3-ethylpentane orrect Answer orrect Answer 2-chloro-4-methylpentane ou Answered ou Answered 3.49 / 3.49 pts Question 16 When ( cis )-1-bromo-2 methylcyclohexane is treated with methanol and heat, four different products are formed — two by substitution and two by elimination. Which of the following conditions would change the outcome of this reaction by promoting the production of 3-methylhexene as the major product? VCU CHEM301 Su21 Midterm #3: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/92107 10 of 22 7/13/2021, 22:40
tert -butoxide/tert-butyl alcohol Correct! Correct! 3.49 / 3.49 pts Question 17 VCU CHEM301 Su21 Midterm #3: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/92107 11 of 22 7/13/2021, 22:40
Predict the most likely mechanism for the reaction shown below. E2 Correct! Correct! 3.49 / 3.49 pts Question 18 Predict the two most likely mechanisms for the reaction of 2-iodohexane with potassium hydroxide. S 2 and E2 Correct! Correct! N VCU CHEM301 Su21 Midterm #3: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/92107 12 of 22 7/13/2021, 22:40
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3.49 / 3.49 pts Question 19 One product which results when 2-chloro-2-methylpentane is heated in ethanol is an ether. From which mechanistic pathway does this ether arise? S 1 Correct! Correct! N 3.49 / 3.49 pts Question 20 VCU CHEM301 Su21 Midterm #3: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/92107 13 of 22 7/13/2021, 22:40
When 3-iodo-3-ethylpentane is treated with sodium methoxide in methanol, the major organic product is an ________ that is generated through an ________ mechanism. alkene; E2 Correct! Correct! 3.49 / 3.49 pts Question 21 What two atomic orbitals or hybrid atomic orbitals overlap to form the C—C σ bond in ethylene? C ( sp ) + C ( sp ) Correct! Correct! 2 2 VCU CHEM301 Su21 Midterm #3: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/92107 14 of 22 7/13/2021, 22:40
3.49 / 3.49 pts Question 22 Which of the following best describes the geometry about the carbon- carbon double bond in the alkene below? E Correct! Correct! 0 / 3.49 pts Question 23 Consider the constitutional isomers 2-methylbut-1-ene, 2-methylbut- 2-ene, and 3-methylbut-1-ene. When each of these alkenes is subjected to catalytic hydrogenation (H , Pt), a single product results. Which of the following best describes the structural relationship among these products? HINT: Hydrogenation is an ADDITION reaction we used to correlated the heat of hydrogenation to the stability of the alkene. What was the 2 VCU CHEM301 Su21 Midterm #3: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/92107 15 of 22 7/13/2021, 22:40
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product of all the heats of hydrogenation reactions? The products are identical. orrect Answer orrect Answer The products are constitutional isomers. ou Answered ou Answered 3.49 / 3.49 pts Question 24 Which of the following alkenes has the largest molar heat of hydrogenation (ie, releases the most heat upon hydrogenation)? 1-hexene Correct! Correct! VCU CHEM301 Su21 Midterm #3: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/92107 16 of 22 7/13/2021, 22:40
0 / 3.49 pts Question 25 Rank the following compounds in order of increasing heat of hydrogenation, Δ H . hyd A < C < B orrect Answer orrect Answer C < A < B ou Answered ou Answered 0 / 3.49 pts Question 26 Which of the following alkenes is the major product when 2-bromo- 2-methylpentane is treated with sodium ethoxide in ethanol? 2-methylpent-2-ene orrect Answer orrect Answer ( E )-4-methylpent-2-ene ou Answered ou Answered VCU CHEM301 Su21 Midterm #3: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/92107 17 of 22 7/13/2021, 22:40
0 / 3.49 pts Question 27 Which of the following alkenes is the major product when 2-bromo- 2-methylpentane is treated with potassium tert -butoxide in tert -butanol? 2-methylpent-1-ene orrect Answer orrect Answer ( E )-4-methylpent-2-ene ou Answered ou Answered 3.49 / 3.49 pts Question 28 Which of the following statements applies to the E2 mechanism? VCU CHEM301 Su21 Midterm #3: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/92107 18 of 22 7/13/2021, 22:40
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The C-H and C-X bonds that break must be anti . Correct! Correct! 0 / 3.49 pts Question 29 By what mechanism does cyclohexanol react when treated in sulfuric acid and what compound results? S 1; methoxycyclohexane ou Answered ou Answered N E1; cyclohexene orrect Answer orrect Answer 3.49 / 3.49 pts Question 30 In the group shown below, which of the following alcohols is (are) likely to yield a product where skeletal rearrangement has occurred when treated with sulfuric acid? 3-methyl-3-pentanol, 3,3-dimethyl-2-butanol, 2,2-dimethylcyclohexanol VCU CHEM301 Su21 Midterm #3: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/92107 19 of 22 7/13/2021, 22:40
both 3,3-dimethyl-2-butanol and 2,2-dimethylcyclohexanol Correct! Correct! 0 / 3.49 pts Question 31 Predict the major product of the reaction shown below. 2,3-dimethyl-2-butene orrect Answer orrect Answer None of the above ou Answered ou Answered 0 / 3.49 pts Question 32 Dehydration of an unknown alcohol with concentrated H SO results in the formation of all of the following alkene products. 2 4 VCU CHEM301 Su21 Midterm #3: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/92107 20 of 22 7/13/2021, 22:40
What is/are the possible structures of the original alcohol? only ou Answered ou Answered both and orrect Answer orrect Answer 3.49 / 3.49 pts Question 33 VCU CHEM301 Su21 Midterm #3: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/92107 21 of 22 7/13/2021, 22:40
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Identify the correct name for the following structure. 6-methoxy-1-methylcyclohepta-1,4-diene Correct! Correct! Quiz Score: 59.33 out of 115.17 VCU CHEM301 Su21 Midterm #3: CHEM-301-002-SU2021 - ORGAN... https://virginiacommonwealth.instructure.com/courses/30623/quizzes/92107 22 of 22 7/13/2021, 22:40
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