[PDF] Organic Chemistry 32-235 Practice Questions for Exam Part 1 PDF 235practice-exam-2-answer.pdf

The Key here is to determine the configuration R or S for each chiral carbon The answer here is 1S, 2S 2 Consider the SN1 reaction of tert-butyl chloride with

Organic Chemistry Questions Which of the following compounds a–d has an IR absorption at 3300 cm–1? a a b b c c d d Organic Chemistry Answers

[PDF] Organic Chemistry 32-235 Practice Questions for Exam Part 1

The Key here is to determine the configuration R or S for each chiral carbon The answer here is 1S, 2S 2 Consider the SN1 reaction of tert-butyl chloride with

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Organic Chemistry 32-235

P r a ctice Questions for Exa m #2

Part 1: (Circle on

l y ONE choice, circling more than one will be counted as wrong!)4 points each

1. 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:

3)3CCl+

I(CH

3)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 ve

The answer is B since e.e. is 40%

favori n g

R. (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) CH

3CH2-Br(B) CH3CH2- Cl(C) CH3CH2-I

(D) CH

3CH2-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 CH

3(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 isomers

C) diastereomers

D) enantiomers

E) None of t

h e above

Again 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 ?

3CH2CH2CH2CH2BrCH

3CH2CH2CHBr

CH 3CH

3CH2CBrCH

3 CH

3(A)(B)(C)

(D) The y will not under g o S

N1 reaction

(E) The y react at the same rate The k e y is to know how a Sn1 reaction pr o ceeds (mec h anism). For Sn1, the leavin g group de p arts before bond formi n g happens. T h erefore t h e intermediate is carb o cation, which is the most stable on a tertia r y carbon. T h e answer is (C). (can y ou e x plain w h y and how the rate d epends on the stabili ty of the intermediate

9. For the following reaction, the overall enthalpy change is:

(A) -12 kcal/mo l (B) +12 kcal/mo l (C) -300 kcal/mol (D) +300 kcal/mo l (E) +15 kcal/mol The k e y here is to understand h o w the heat o f the reaction is rela t ed to bond dissociation ener gy (BD E ) and the d efinition of BDE.

Also it is essential to know that bond breaki

n g requires e n er g y.

The answer is (A)

10. Which of the following alkyl halides would you expect to give the highest yield of substitution

product (S

N2) with CH3CH2O- Na+ ?

3CH2CH2CH2CH2BrCH

3CH2CH2CHBr

CH 3CH

3CH2CBrCH

3 CH

3(A)(B)(C)

(D) The y will g ive same y ield of substitution products (E) None of them g ives substitution products

For SN2, the nuc

l eophile has to attack from the back of the leavi n g g roup. Theref o re the carbon bein g attacked must not be ster i cal l y hindered, otherwise elimination will compete. The answer here is (A) which would g ive the b est y i eld of substitution product.CH

3CH2CH2Br + HBrCH

quotesdbs_dbs9.pdfusesText_15

[PDF] [PDF] Organic Chemistry 32-235 Practice Questions for Exam Part 1

Organic Chemistry 32-235

Part 1: (Circle on

1. The correct

2. Consider the SN1 reaction of tert-butyl chloride with iodide ion:

3)3CCl+

3)3CICl+

3. The relationship between the following two structures is:

4. The specific rotation of pure (R)-2-butanol is -13.5°. What % of a mixture of the two

The answer is B since e.e. is 40%

R. (5.4/13.5=4

3CH2-Br(B) CH3CH2- Cl(C) CH3CH2-I

3CH2-F(E) they react at the same rate

6. Which of the following molecules is chiral ?

3(A)(B)(C)

7. The relationship between (A) and (B) structures in the previous question is:

A) identical

B) struct

C) diastereomers

D) enantiomers

E) None of t

Again need to know terms and how to app

3CH2CH2CH2CH2BrCH

3CH2CH2CHBr

3CH2CBrCH

3(A)(B)(C)

N1 reaction

9. For the following reaction, the overall enthalpy change is:

Also it is essential to know that bond breaki

The answer is (A)

10. Which of the following alkyl halides would you expect to give the highest yield of substitution

N2) with CH3CH2O- Na+ ?

3CH2CH2CH2CH2BrCH

3CH2CH2CHBr

3CH2CBrCH

3(A)(B)(C)

For SN2, the nuc

3CH2CH2Br + HBrCH