Chem 30A Fall 2004 QUIZ #2 (BLUE) Weds Nov 10th

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1 Last Name ANSWER First Name KEY MI Student I Number: Circle the name of your TA: iscussion Section ay: Cari / Phil / Adam / eather Time: Total Score 35 / 30 Chem 30A Fall 2004 QUIZ #2 (BLUE) (15 Min) Weds Nov 10th INTERPRETATIN F TE QUESTINS IS PART F TE EXAM NT ASK FR TE QUESTINS T BE EXPLAINE T YU USE CAPITAL LETTERS WEN FILLING IN TE BXES AN BE CLEAR IF WE CAN'T FIGURE UT WAT A LETTER IS, IT WILL AUTMATICALLY BE GRAE AS INCRRECT *** NT PEN TIS EXAM UNTIL INSTRUCTE T S*** Q Total E B C C E B B E E 30 ANSWER T BNUS QUESTIN This one more likely or 5

EXPLAINE T YU USE CAPITAL LETTERS WEN FILLING IN TE BXES AN BE CLEAR IF WE CAN'T FIGURE UT WAT A LETTER IS, IT WILL AUTMATICALLY BE GRAE AS

2 Being eaten by a crocodile is just like going to sleep... in a giant blender omer J Simpson Questions 1 10 are worth 3 points each. The bonus is worth 5 points. 1. What is the MAJR product of the reaction shown below C 4 A B C E 2. What is the order of acidity (from lowest pk a value to highest pk a value) of the bold hydrogen () atoms shown highlighted in the compounds drawn below A 3, 4, 2, 1 B 4, 2, 1, 3 C 3, 1, 4, 2 2, 4, 3, 1 E 4, 3, 1, 2 3. The equilibrium constant (K eq ) for the reaction shown below is... Acid + Base Conjugate Acid + Conjugate Base pk a = 19 pk a = 21 A 2 B 100 C E 40 1

What is the order of acidity (from lowest pk a value to highest pk a value) of the bold hydrogen () atoms shown highlighted in the compounds drawn below

3 4. Which of the compounds drawn below is the strongest base A N 4 B N 3 C NaN 2 C 3 N 2 E 5. ydroboration/oxidation of 1-methylcyclohexene with deuterated borane TF (reacts just like B 3 TF, but has atoms instead of ) gives which compound N 2 (i) B 3 TF (ii) 2 2 / Na A B C E 6. What is the MAJR product of the reaction shown below 2 2 S 4 (cat.) A B C E 2,2-dimethyl-propan-1-ol 3-methyl-butan-2-ol 3-methyl-butan-1-ol 2-methyl-butan-1-ol 2-methyl-butan-2-ol 7. The product(s) of the reaction shown below are 2 C A nly 1 B nly 2 C nly 3 nly 1 and 3 E 1, 2, and 3 2

compound N 2 (i) B 3 TF (ii) 2 2 / Na A B C E 6. What is the MAJR product of the reaction shown below 2 2 S 4 (cat.

4 8. Which combination(s) of reagents would give rise to the reaction shown below #1 (i) B 3 TF (ii) 2 2 / Na #2 (i) g(ac) 2 / 2 (ii) NaB 4 #3 2 / 2 S 4 (cat.) A nly #1 B nly #2 C nly #3 nly #2 and #3 E #1, #2, and #3 9. What is the MAJR product of the reaction shown below 2 2 A B C E 10. Which of the three alkenes drawn below will react with in ether (solvent) to give 2-bromo-2-methylbutane A nly 1 B nly 2 C nly 3 nly 1 and 3 E 1, 2, and 3 BNUS: The reaction of 5-hexen-1-ol with bromine in ether (solvent) gives a compound with the molecular formula C raw what you think the product of this reaction is N TE FRNT CVER of this quiz in the box provided. 2 ether C

Which of the three alkenes drawn below will react with in ether (solvent) to give 2-bromo-2-methylbutane 1 2 3 A nly 1 B nly 2 C nly 3 nly 1 and 3 E 1, 2, and 3 BNUS: The

5 Last Name ANSWER First Name KEY MI Student I Number: Circle the name of your TA: iscussion Section ay: Cari / Phil / Adam / eather Time: Total Score 35 / 30 Chem 30A Fall 2004 QUIZ #2 (PINK) (15 Min) Weds Nov 10th INTERPRETATIN F TE QUESTINS IS PART F TE EXAM NT ASK FR TE QUESTINS T BE EXPLAINE T YU USE CAPITAL LETTERS WEN FILLING IN TE BXES AN BE CLEAR IF WE CAN'T FIGURE UT WAT A LETTER IS, IT WILL AUTMATICALLY BE GRAE AS INCRRECT *** NT PEN TIS EXAM UNTIL INSTRUCTE T S*** Q Total C B E A E C B A 30 ANSWER T BNUS QUESTIN 6-membered ring more stable or 5

6 Being eaten by a crocodile is just like going to sleep... in a giant blender omer J Simpson Questions 1 10 are worth 3 points each. The bonus is worth 5 points. 1. What is the MAJR product of the reaction shown below C 4 A B C E 2. What is the order of acidity (from lowest pk a value to highest pk a value) of the bold hydrogen () atoms shown highlighted in the compounds drawn below A 2, 4, 3, 1 B 4, 3, 1, 2 C 3, 1, 4, 2 3, 4, 2, 1 E 4, 2, 1, 3 3. The equilibrium constant (K eq ) for the reaction shown below is... Acid + Base Conjugate Acid + Conjugate Base pk a = 19 pk a = 21 A 2 B 0.01 C 2 40 E 100 1

7 4. Which of the compounds drawn below is the strongest base A NaN 2 B C 3 N 2 C N 3 E N 4 5. ydroboration/oxidation of 1-methylcyclohexene with deuterated borane TF (reacts just like B 3 TF, but has atoms instead of ) gives which compound N 2 (i) B 3 TF (ii) 2 2 / Na A B C E 6. What is the MAJR product of the reaction shown below 2 2 S 4 (cat.) A B C E 2,2-dimethyl-propan-1-ol 3-methyl-butan-2-ol 3-methyl-butan-1-ol 2-methyl-butan-2-ol 2-methyl-butan-1-ol 7. The product(s) of the reaction shown below are 2 C A nly 1 and 3 B 1, 2, and 3 C nly 2 nly 1 E nly 3 2

8 8. Which combination(s) of reagents would give rise to the reaction shown below #1 (i) B 3 TF (ii) 2 2 / Na #2 (i) g(ac) 2 / 2 (ii) NaB 4 #3 2 / 2 S 4 (cat.) A #1, #2, and #3 B nly #2 and #3 C nly #1 nly #2 E nly #3 9. What is the MAJR product of the reaction shown below 2 2 A B C E 10. Which of the three alkenes drawn below will react with in ether (solvent) to give 2-bromo-2-methylbutane A 1, 2, and 3 B nly 1 and 3 C nly 3 nly 2 E nly 1 BNUS: The reaction of 4-hexen-1-ol with bromine in ether (solvent) gives a compound with the molecular formula C raw what you think the product of this reaction is N TE FRNT CVER of this quiz in the box provided. 2 ether C

Which of the three alkenes drawn below will react with in ether (solvent) to give 2-bromo-2-methylbutane 1 2 3 A 1, 2, and 3 B nly 1 and 3 C nly 3 nly 2 E nly 1 BNUS: The

9 Last Name ANSWER First Name KEY MI Student I Number: Circle the name of your TA: iscussion Section ay: Cari / Phil / Adam / eather Time: Total Score 35 / 30 Chem 30A Fall 2004 QUIZ #2 (BUFF) (15 Min) Weds Nov 10th INTERPRETATIN F TE QUESTINS IS PART F TE EXAM NT ASK FR TE QUESTINS T BE EXPLAINE T YU USE CAPITAL LETTERS WEN FILLING IN TE BXES AN BE CLEAR IF WE CAN'T FIGURE UT WAT A LETTER IS, IT WILL AUTMATICALLY BE GRAE AS INCRRECT *** NT PEN TIS EXAM UNTIL INSTRUCTE T S*** Q Total B C B B B C 30 ANSWER T BNUS QUESTIN 6-membered ring more stable, but 5-membered product puts δ+ on carbon better able to stabilize it in the transition state (2 vs 1 ) or 5

BXES AN BE CLEAR IF WE CAN'T FIGURE UT WAT A LETTER IS, IT WILL AUTMATICALLY BE GRAE AS INCRRECT *** NT PEN TIS EXAM UNTIL INSTRUCTE T S*** Q 1 2 3 4 5 6 7 8 9 10 Total B

10 Being eaten by a crocodile is just like going to sleep... in a giant blender omer J Simpson Questions 1 10 are worth 3 points each. The bonus is worth 5 points. 1. What is the MAJR product of the reaction shown below C 4 A B C E 2. What is the order of acidity (from lowest pk a value to highest pk a value) of the bold hydrogen () atoms shown highlighted in the compounds drawn below A 2, 4, 3, 1 B 3, 1, 4, 2 C 4, 3, 1, 2 3, 4, 2, 1 E 4, 2, 1, 3 3. The equilibrium constant (K eq ) for the reaction shown below is... Acid + Base Conjugate Acid + Conjugate Base pk a = 19 pk a = 21 A 2 B 2 C E 40 1

11 4. Which of the compounds drawn below is the strongest base A C 3 N 2 B NaN 2 C N 3 E N 4 5. ydroboration/oxidation of 1-methylcyclohexene with deuterated borane TF (reacts just like B 3 TF, but has atoms instead of ) gives which compound N 2 (i) B 3 TF (ii) 2 2 / Na A B C E 6. What is the MAJR product of the reaction shown below 2 2 S 4 (cat.) A B C E 2,2-dimethyl-propan-1-ol 2-methyl-butan-2-ol 3-methyl-butan-2-ol 3-methyl-butan-1-ol 2-methyl-butan-1-ol 7. The product(s) of the reaction shown below are 2 C A nly 1 and 3 B 1, 2, and 3 C nly 3 nly 2 E nly 1 2

12 8. Which combination(s) of reagents would give rise to the reaction shown below #1 (i) B 3 TF (ii) 2 2 / Na #2 (i) g(ac) 2 / 2 (ii) NaB 4 #3 2 / 2 S 4 (cat.) A #1, #2, and #3 B nly #1 C nly #2 nly #3 E nly #1 and #3 9. What is the MAJR product of the reaction shown below 2 2 A B C E 10. Which of the three alkenes drawn below will react with in ether (solvent) to give 2-bromo-2-methylbutane A nly 2 B nly 1 and 3 C nly 1 1, 2, and 3 E nly 3 BNUS: The reaction of 5-hexen-2-ol with bromine in ether (solvent) gives a compound with the molecular formula C raw what you think the product of this reaction is N TE FRNT CVER of this quiz in the box provided. 2 ether C

Which of the three alkenes drawn below will react with in ether (solvent) to give 2-bromo-2-methylbutane 1 2 3 A nly 2 B nly 1 and 3 C nly 1 1, 2, and 3 E nly 3 BNUS: The

CHM 2210: ORGANIC CHEMISTRY II Third Exam, Form 3 Section 02, Professor A. Herriott November 29, 2007

CHM 2210: ORGANIC CHEMISTRY II Third Exam, Form 3 Section 02, Professor A. Herriott November 29, 2007 CM 2210: ORGANIC CEMISTRY II Third Exam, Form 3 Section 02, Professor A. erriott November 29, 2007 No electronic devices (calculators, cell phones, laptops, etc) may be used or consulted during the exam.