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Dec 6, 2023

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1 Name: ____________________________________________ CHM 355 Final Exam Review Questions, Extra Credit 1. Give the IUPAC name for the following compound: 2. Give the IUPAC name for the following compound: 3. Draw the structure for 3-ethyl-5-isobutylnonane. 4. Draw both chair conformations for the following structure. 5. Draw the skeletal structure for trans- 1-ethyl-2-methylcyclopentane. 6. Draw a Newman projection for the following structure from the direction indicated. Cl Br NH 2 CH 3 viewing direction
2 7. Draw the cis and trans isomers for the following structure. 8. How are the following two structures related? a) identical b) enantiomers c) diastereomers d) constitutional isomes e) not isomers 9. Classify the transformation as oxidation, reduction, or neither. 10. Classify the following transformation as oxidation, reduction, or neither. 11. Identify the formal charges on nitrogen and oxygen. 12. Draw a resonance structure for the following compound. Be sure to include all formal charges and non-bonding electrons. 13. Are the following structures isomers, resonance forms, or neither? H H H O OH O H H H H H H N O O C H 3 C H 3 C H 3 C H 3
3 14. Draw a resonance structure for the following species. 15. What orbitals are used to form each bond in methanol, CH 3 OH? C-H _______________________ C-O _______________________ O-H _______________________ 16. Determine the hybridization around each of the indicated carbon atoms in propyne. 17. Label all bonds in acetonitrile as being either polar or nonpolar. C-H bonds ____________________ σ and π C-N bonds _________________ C-C σ bonds ___________________ 18. Draw a Fischer projection for the following molecule and label the stereocenter as either S or R. 19. Draw a structure using dashes and wedges and label the stereocenter as R or S . 20. Convert the following structure into a Fischer projection and label the stereocenters as R or S . O CH 3 C H C H 3 C N H O H O H Cl H H O O H OH O H OH OH
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4 21. Draw the following structure using dashes and wedges. Additionally, identify the stereocenters as R or S . 22. Draw in the conjugate acid and the conjugate base in this acid-base equilibrium expression. Are the products or the reactants favored? 23. Draw in the conjugate acid and the conjugate base for the acid-base reaction shown below. 24. Which of the following bases can deprotonate the alkyne shown below? Circle all correct answers. a) CF 3 CO 2 Na b) NaCN c) CH 3 NHNa d) CH 3 Li e) NaOH f) NaCH 2 (CO)N(CH 3 ) 2 25. Rank the bases from least basic to most basic: CH 3 NH - , CH 3 CH 2 - , CH 3 O - 26. Identify the functional groups in the following structures: a) ester, b) ether, c) alcohol, d) carboxylic acid, e) amine, f) amide, and g) alkene. OH O H OH O H H H OH H OH OH O C H 3 O + C H 3 CH 3 O + H 2 SO 4 C H 3 CH OH O O H O H OH O O O NH O NH 2 10 steps
5 27. What type of intermolecular forces are present in butanoic acid? Circle all correct answers. a) hydrogen bonding b) dipole-dipole c) ionic bonding d) van der Waals 28. What type of intermolecular forces are present in pyridine? Circle all correct answers. a) hydrogen bonding b) dipole-dipole c) ionic bonding d) van der Waals 29. Rank the following compounds in order of increasing strength of intermolecular forces: 30. Rank the following compounds from highest to lowest boiling point. 31. Rank the following compounds from least to most water soluble. 32. Rank the following compounds from lowest to highest boiling point. 33. Is the following molecule chiral or achiral? How do you know? (Hint: you may need to rotate about the C 2 -C 3 bond) OH O N O OH O O OH Br OH O OH OH Br H Br Br H
6 34. Draw the mirror image of the molecule drawn below. Are these molecules chiral or achiral? 35. Determine the number of stereogenic centers in the following molecule. 36. How many stereoisomers could be drawn for the following molecule? Draw all the possibilities using dashes and wedges to indicate stereochemistry where appropriate. 37. Rank the following groups in order of decreasing priority when determining R or S . 38. Label the following stereocenters as R or S . 39. Draw the structure for (4 R ,5 S )-4,5-diethyloctane. H OH OH OH O N Br CH 3 CH 3 CH 3 OH Cl Cl CH CH 2 C CH CH 3 H O H Br OH Br
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7 40. Place another methyl group on the structure below to make the structure a meso compound. 41. What type of strain can be found in the following molecule? Circle all correct answers. a) steric b) torsional c) both a and b 42. Draw a Newman projection for the molecule shown in #41. Draw a Newman projection of the ethyl groups gauche. 43. Pure monosodium glutamate, a common flavor enhancer, exhibits a specific rotation of +24 o . Calculate the ee of a solution whose [ α ] is +12. 44. The equilibrium constant for the conversion of the axial to the equatorial conformation of methoxycyclohexane is 2.7. Given this data, which conformation is present in the larger amount at equilibrium? Circle your answer. 45. Which of the profiles is exothermic? Which is endothermic? Which profile represents the fast reaction? Br H H Cl Cl O H O H
8 46. What would an energy diagram with two steps look like? You may select one from the book and draw it here. Be sure to label your diagram. 47. Give the IUPAC name for the following compound. 48. Determine the product(s) of the reaction. 49. Circle the following molecule(s) which have good leaving groups. 50. Rank the species in order of nucleophilicity in acetone. CH 3 OH CH 3 NH 3 CH 3 SH 51. Rank the species in order of increasing nucleophilicity in CH 3 OH. - OH - SH H 2 O 52. Draw in the product(s) of the following reaction and indicate stereochemistry where appropriate. Br I NaCN Br O + H H OH NaCN I
9 53. Which S N 2 reaction in the following pair is fastest? 54. Rank the alkyl halides in the following group in order of increasing S N 2 reactivity. 55. Draw the mechanism for the following reaction and predict the product(s). 56. Draw the mechanism for the following reaction. 57. Predict the product(s) of the reaction. Br Br NaOCH 2 CH 3 NaOCH 2 CH 3 or Br Br Br I H 2 O I CH 3 OH O DMSO Br NaOCH 3
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10 58. Draw the structure of the alkyl halide that was used to prepare the alkene produced as the only product. 59. Rank the following alkenes from most to least stable. 60. Rank the following alkyl halides in order of increasing reactivity in an E2 reaction. 61. Predict the elimination products of the following reaction. Label the major and minor products. 62. Draw the structure of an alkyl halide from which the alkene below was prepared. 63. Explain the following observation: Treatment of alkyl chloride A with NaOCH 2 CH 3 yields only one product B, whereas treatment of A with very dilute base in CH 3 CH 2 OH yields a mixture of B and C, with C predominating. Select the single best answer. a) switching from concentrated to dilute base shifts the mechanism from E2 to E1 b) Using dilute base allows a byproduct to form via the S N 2 mechanism c) The antiperiplanar requirement of the E1 mechanism causes two products to form d) Some of the carbocation intermediate of the E2 mechanism rearranges, leading to a second product Br Br Br NaOH Br Cl A B C
11 64. Predict the S N 1 and E1 products of the following reaction. 65. Draw the mechanism for the following reaction and predict the product. 66. Draw the alkynes that are formed when the geminal dihalide is treated with excess base. 67. Predict the major product of the reaction when the substrate is treated with three different reagents (one product per reagent). a) NaCH 3 CO 2 b) KOC(CH 3 ) 3 c) NaOCH 3 68. Predict the five products (2 for S N 1 and 3 for E1) that could form as a result of this reaction. Rank the E1 products from most to least produced. Cl CH 3 CH 2 OH Cl KOCH 3 excess NaNH 2 Br Br a, b, or c Cl H Cl H 2 O
12 69. Classify the following alcohol groups as primary, secondary, or tertiary. 70. Draw the structure for 2- tert -butyl-3-methylcyclohexanol. 71. Give the IUPAC name for the following structure. 72. Draw the mechanism and predict the product of the following reaction. O O H H O OH OH OH OH 1. NaH 2. Br
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13 73. Identify the starting material in the following chemical reaction and draw the mechanism for the formation of the product. 74. Predict the product(s) of the reaction and draw the mechanism. 75. Provide the product for the following reaction. 76. Provide the product for the following reaction. H 2 SO 4 H 2 SO 4 (cat) H 2 O O H HCl OH PBr 3
14 77. Design a multi-step synthesis using only the reagents provided in the box. Br 2 HBr acetone TsCl NaN 3 NaOH pyridine H 2 O NaBr DMSO EtOH SOCl 3 H 2 SO 4 78. Place the reagents necessary for the synthetic pathway in the boxes provided. 79. Predict the product of the reaction. 80. Design a multi-step synthesis using only the reagents provided in the box. mCPBA CH 2 Cl 2 PCC H 2 O H 2 SO 4 OsO 4 NaH O 3 DMSO NaCN HCN HgSO 4 OH H H N 3 OH O OH O 1. OsO 4 2. NaHSO 3 , H 2 O O N
15 81. Determine the diyne that was used to prepare the following reactants. 82. Give the products of the oxidative cleavage of the alkene shown below. Additionally, provide the other reagents needed. 83. Predict the product of the following reaction. 84. Design a multi-step synthesis using only the reagents provided in the box. H 2 Lindlar’s cat. O 3 Li NaOH H 2 O CH 3 OH NH 3 CH 3 SCH 3 mCPBA LiAlH 4 Pt H 2 SO 4 NaBH 4 85. Provide the reagents necessary for the following reaction. O OH O H O OH O OH O 1. 2. O H OH O H OH O 1. LiAlH 4 2. H 2 O
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16 86. Draw the structure of the reactant used to prepare the following products using the conditions supplied below. 87. Using the reagents presented in the multi-step synthesis, identify compounds A-E. 88. Design a multi-step synthesis using only the reagents provided in the box. NaH Br 2 BH 3 HBr HgSO 4 H 2 O NaOH H 2 O 2 H 2 SO 4 CH 3 CH 2 Br O 3 Zn O H O + 1. O 3 2. Zn, H 2 O A B C D E KOC(CH 3 ) 3 Br 2 2 eq. KOC(CH 3 ) 3 DMSO NaNH 2 CH 3 I H H H O
17 89. What acetylide ion and alkyl chloride can be used to prepare the following alkyne? 90. Predict the product of the following reaction. 91. Predict the product of the following reaction. 92. Which of the following can deprotonate acetylene? Select all correct answers. a) CH 2 CH - b) CH 3 CH 2 S - c) CH 3 CH 2 - d) (CH 3 ) 3 CO - e) CH 3 CO 2 - f) NaNH 2 g) NaH h) NaOH 93. Identify the missing reagents in the multistep synthesis. 94. Draw a mechanism for the following reaction. 1. R 2 BH 2. H 2 O 2 , NaOH HgSO 4 H 2 SO 4 , H 2 O H H Cl OH O OH 1. 2. OH H 2 O H 2 SO 4
18 95. Draw the structures for ( Z )-2-bromo-1-iodohex-1-ene and ( E )-3,5,6-trimethyloct-2-ene 96. Give the IUPAC name for the following structure. 97. Which of the following has the lowest heat of hydrogenation? 98. What series of reagents are necessary in syn dihydroxylation? There are two synthetic routes. List both of them. 99. Draw the product of the reaction between the alkyne (shown below) under the four different conditions provided, a-d. a) H 2 (excess), Pd-C b) H 2 (1 equivalent), Lindlar’s catalyst c) Na, NH 3 d) H 2 (excess), Lindlar’s catalyst OH OH OH ? O
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19 100. Pure (+)- R -limonine has a boiling point of 176 o C and an [ α ] of +115.5 o . The structure of (+)- R -limonine is shown below. What can be said about (-)- S -limonine in terms of its physical properties in comparison? Draw the structure of (-)- S -limonene.

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Related Questions
2
find out correct and incorrect IUPAC name and give reason behind it!
Part L Give any common name for the following compound. Br CI If the compound has only the IUPAC name, enter no. Submit Request Answer Part J Give any common name for the following compound. Br CH3 If the compound has only the IUPAC name, enter no. 1-bromo-2-methylbenzene Submit Previous Answers Request Answer X Incorrect; Try Again
urgent help plese
A Moving to another question will save this response. Question 29 What is the correct IUPAC name for 4,6-diethylheptane. HINT: Draw the molecule as written in the question, look for the longest chain, then correctly name. O 2,4-diethylheptane O 5-ethyl-3-methyloctane O isoheptane O 3-methyl-5-propylheptane O 4-ethyl-6-methyloctane A Moving to another question will save this response. MacBook Air 888 DII DD F1 F2 F3 F4 FS F6 F9 F7 F8 @ #3 $ % & * 2 3 4 7 8. Q W E Y U A S F J K C M command
2. A student named a compound as 6-methyl-6-ethylhept-1-en-5-one. Even though one can draw a correct structure based on that name, the name itself is incorrect according to the IUPAC naming conventions. Draw a structure for the compound (based on the above name), and then name the compound correctly. Structure Correct Name
#20
Pls answer the question attached in the image
Question 3
Please help me draw these structures
18-Draw the structure corresponding to each IUPAC name
Give the IUPAC name for the given compound. Step 7: Put all the pieces together and name the alkene. IUPAC Name: (Z)-3-(1'methyl)ethyl-4-propyloct-3-ene Incorrect • Step 1: Identify the number of carbons in the longest chain • Step 2: Identify the parent chain from 3 options • Step 3: Construct the parent name • Step 4: Identify substituents and locants • Step 5: Identify substituent order • Step 6: Prioritize substituents and determine
1. Draw the following molecules given their IUPAC name. a) 3-Methylheptane b) 3-isopropyl-2-methylhexane c) 2,2,4-trimethylpentane d) 2,2,7-trimetthyloctane e) 2-bromo-1,1-dimethylcyclohexane f) 2-methyl-1-ethyl-1,3-dipropylcyclopentane 2. Although a structure can be drawn for 2-methyl-2-isopropylheptane, the molecule is not named correctly using IUPAC rules. Draw the structure, and then give the appropriate IUPAC name for the molecule.
#13 question A only
#13 question B only
Please re do over the work and check it it correct
Using IUPAC guidelines, name the following organic compound HHH H | | | | H-C-C-C-C-H Answer: butane Using IUPAC guidelines, name the following organic compound Answer: Using IUPAC guidelines, name the following organic compound H H that C H H H H H HH H Answer: Using IUPAC guidelines, name the following organic compound CH₂ CH₂-CH₂-C-CH-CH₂-CH₂ CH₂ CH₂ CH₂ Answer: -H Using IUPAC guidelines, name the following organic compound Ź Answer:
34
None
Question 9
Wondershare PDFelement Pro File Edit View Tool Go Window Help 76% [4) A АBC Fri 12:32 PM 11. Which of the following is the structural formula for methyl methanoate? A. H H В. нн Н-с—С- о-с-н H-C-0- C-C-H H H H C. H D. H || Н-С нн H-C-0-C H. С-С-н H. H нн
2. Draw the structure of following compounds: a) 2-methoxypentane b) 1-isopropoxy-3-methylbutane
College Chemistry II CHE 132 Test #1 - Part B 1. The following names are incorrect by IUPAC rules. Draw a condensed structural formula for each molecule listed and give the correct IUPAC name. a) 3-propyl-4-hexyne b) 1,4-dimethyl-5-cylcopentene CH2 CH2 CH3 CH3-CH2 -CH- C=CH c) 2-sec-butyl-4-pentene d) 2,4-diethyl-2-methylpentane 2. Write the balanced equation for the complete combustion of a hydrocarbon of your choice. Name the hydrocarbon used in the reaction.
Question 31
What is the IUPAC name for the following substituted benzene? NO2 Br NO2 Select one: O a. 1-bromo-2,5-dinitrobenzene O b. 3-bromo-1,4-dinitrobenzene O c. p-dinitro-2-bromo-benzene O d. 2-bromo-1,4-dinitrobenzene O e. 1-bromo-3,6-dinitrobenzene
Write the IUPAC name for the compound below. Be sure to use correct punctuation. VA LISO.L Accepted names for branched alkyl groups are isopropyl, isobutyl, sec-butyl, and tert-butyl. Do not use italics. CH3 CH₂CH₂CCH₂CH₂CH(CH3)2 CH3 The IUPAC name is Submit Answer Retry Entire Group 9 more group attempts remaining
Can someone help me name this compound? I got 5-propyl-4-sec-butyl-3methyloctane, but I don't think it's right.
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