Organic Chemistry 32-235 Practice Questions for Exam #2 Part 1: (Circle only ONE choice, circling more than one will be counted as wrong) 4 points each 1
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[PDF] Organic Chemistry 32-235 Practice Questions for Exam Part 1
Organic Chemistry 32-235 Practice Questions for Exam #2 Part 1: (Circle only ONE choice, circling more than one will be counted as wrong) 4 points each 1
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Organic Chemistry 32-235
P r a ctice Questions for Exa m #2Part 1: (Circle on
l y ONE choice, circling more than one will be counted as wrong!)4 points each1. The correct
I UPAC n ame for the followin g compound is: (A) (1R, 3R)-1-chloro-3- m et h y lc y clohe x ane (B) (1R, 3S)-1-chlor o -3-met h y l c y clo h e x ane (C) (1S, 3S)-1-chlor o -3-met h y l c y clo h e x ane (D) (1S, 3R)-1-chloro-3- m et h y lc y clohe x ane (E) None of the above. The K e y here is to determine the conf i g uration R or S for each chiral carbon. The answer h ere is 1S, 2S.2. Consider the SN1 reaction of tert-butyl chloride with iodide ion:
CH3)3CCl+
I(CH3)3CICl+
I f the co n centration of iodide ion is doubled, the rate of formi n g tert-bu t y l iodide will: (hint: consider mechanism, i.e. how is the p roduct for m ed (A) Double (B) I ncrease 4 times (C) Remain the same. (D) Decrease (E) None o f the abo v e. I n SN1 reaction, the rate is inde p endent of the n u cleophile involved since the nucleophile is not involved in the rate determinin g step. Thus the anwer is C.3. The relationship between the following two structures is:
(A) e n antiomer s (B) dias t ereomer s (C) structural isomers (D) identica l (E) none of t h e above The k e y here is to know the definition of all terms and then determine R or S conf i g uration f o r each chiral carbon. The answer is (B) b y definition)4. The specific rotation of pure (R)-2-butanol is -13.5°. What % of a mixture of the two
enantiomeric f o rms is (S)-2-butanol if the specific ro t ation of this mixture is -5.4° ? (A) 40 (B) 3 0 (C) 60 (D) 70 (E) None o f the abo veThe answer is B since e.e. is 40%
favori n gR. (5.4/13.5=4
0 %)CH 3H Cl HCH 3 HOH OHH CH 3CH 3 HOH OHH CH 3 Page 2/95. Which of the following alkyl halides would undergo SN2 reaction most rapidly? (A) CH3CH2-Br(B) CH3CH2- Cl(C) CH3CH2-I
(D) CH3CH2-F(E) they react at the same rate
I n Sn2 reaction, the n u cleophile attacks from the back of the leavi n g g roup. The b etter the leavi ng g roup, t h e easier it is to leave (faster rate). T h e answer is C since iodide ion is the best leavi ng g roup.6. Which of the following molecules is chiral ?
CH 3CH3 H HCH 3H H CH3OH CH3(A)(B)(C)
CCCH 3 HCH 3 HCCH CH 3CH 3 H(D) (E) Go b y d efinition or look for plane o f s y m m et r y /point of in v ersion. The answer is B.7. The relationship between (A) and (B) structures in the previous question is:
A) identical
B) struct
u ral isomersC) diastereomers
D) enantiomers
E) None of t
h e aboveAgain need to know terms and how to app
l y them. The answer is C.Page 3/98. Which of the following alkyl halides would you expect to undergo SN1 reaction most rapidly ?
CH