Exam 2 CHM 235 Spring 2012 Robinson

Name ___KEY_______________

Part 1. Multiple Choice (20 at 5 points each = 100 points)

1. What functional groups are present in the following molecule? a) Amide, alcohol, ester, amine b) Aromatic, alcohol, ketone, amide c) Alcohol, amine, ester d) Alcohol, amide, ester

2. What functional groups are present in the following molecule? a) Aldehyde and ester b) Aldehyde and ketone c) Aldehyde and ether d) Ketone and carboxylic acid

3. Which of the following compounds is MORE acidic than CH3CH2CCH? a) CH3CH2NH2 b) CH3CH2CH=CH2 c) CH3CH2OH d) CH3CCCH3

4. BF3 and C(CH3)+ are both examples of a) carbanions b) Lewis bases c) carbocations d) Lewis acids

Consider the following reaction for questions 5-7:

H N N H

CH3OCH3

CH3OCH3

II

III

IV

5. Which compound is the conjugate acid? a) I b) II c) III d) IV

6. Which compound is the base? a) I b) II c) III d) IV

7. The pKa of a protonated amine is about 9.0. The pKa of a protonated ether is about -3.8. Given that information, what is true about the equilibrium of the reaction? a) Equilibrium lies to the left, hence Ka < 1 b) Equilibrium lies to the left, hence Ka > 1 c) Equilibrium lies to the right, hence Ka > 1 d) Equilibrium lies to the right, hence Ka < 1 8. Phenol (C6H5OH) is a stronger acid than cyclohexanol due to ______________ a) Hydrogen bonding b) Resonance stabilization of conjugate base c) Resonance stabilization of conjugate acid d) Electronegativity

9. HBr is a stronger acid than HCl due to _____________ a) Inductive effects b) Resonance stabilization of conjugate base c) Size of conjugate base d) Electronegativity of conjugate base 10. CH2=CH2 is a weaker acid than CH3CCH due to ____________ a) Inductive effects b) Size of conjugate base c) Electronegativity of conjugate base d) Hybridization of orbital with minus charge 11. Which Newman projection accurately represents 4-bromo-3,3-dimethylhexane? A
CH2CH3 Br H3C H CH3 CH2CH3 Br CH2CH3 CH3 CH3 CH2CH3 Br H3C CH2CH3 H CH2CH3 CH2CH3 Br H3C CH3 CH2CH3 H CH2CH3

(a)

(b)

(c)

(d)

12. Which isomer of C3H6O would produce a strong absorbance at 1710 cm-1 as its only major absorbance? D (Ketone)
OH O OH O

(a)

(b)

(c)

(d)

13. Which isomer of C4H6O would produce a sharp peak around 2200 cm-1 and another sharp peak around 3300 cm-1 as its only major absorbances? A (Terminal alkyne)
O

CH3OCH2C

CH
OH

CH3C

CCH2OH

(a)

(b)

(c)

(d)

14. How many AXIAL hydrogren atoms are there in the lowest energy chair conformation of trans1,4-dimethylcyclohexane? a) 3 b) 4 c) 5 d) 6

15. Which is the HIGHEST ENERGY conformation of hexane viewed down the C3-C4 bond? A
H3CH2C CH2CH3 H CH2CH3 H H CH2CH3 H CH2CH3 CH2CH3

H H

H H

H CH2CH3

H H H

CH2CH3 H

H H

(a)

(b)

(c)

(d)

16. What is the correct IUPAC name for the following compound? a) 3-ethyl-5-methyl-6-propyloctane b) 6-ethyl-4-methyl-3-propyloctane c) 3,6-diethyl-5-methylnonane d) 4,7-diethyl-5-methyloctane

17. What is the correct IUPAC name for the following compound? a) b) c) d) 2,4-dimethyl-5-(1-hydroxylpropyl)heptane 4-ethyl-5,7-dimethyl-3-octanol 2,4-dimethyl-5-ethyl-3-octanol 1,2-diethyl-3,5-dimethyl-1-hexanol

18. Which is the MOST ACIDIC proton in the following compound? A

Ha O
Hb

H2C Hd

N Hc

19. How many gauche interactions are there in the following conformation? a) 0 b) 1 c) 2 d) 3

20. Which compound will have the highest boiling point? a) Cyclohexane b) Cyclohexene c) Cyclohexanol d) Bromocyclohexane

GO ON TO THE SHORT ANSWER QUESTIONS

Multiple choice = _________points (100 max) Short answer = _________points (50 max) Total = _______ points out of 150 or ______%

Part 2: Short Answer 1. Draw and name 5 alcohols with the formula C6H14O. (Use stick or condensed structures). Here are a few. Structure
OH

IUPAC Name
1-hexanol

2-hexanol
OH

OH

3-hexanol

OH

2-methyl-1-pentanol

OH

3-methyl-1-pentanol

OH

4-methyl-1-pentanol

OH

2-methyl-3-pentanol

2-methyl-2-pentanol
OH

OH

2,3-dimethyl-1-butanol

2. (Part a) Give IUPAC names for the following three compounds:

Cl

5-bromo-1-chloro-1-cyclohexene (or 5-bromo-1-chlorocyclohexene)

Br

OH

2-cyclopenten-1-ol (or 2-cyclopentenol)

4-ethyl-5-methyl-3-hexanol
OH

2. (Part b) Draw structures for the following compounds:

5-(1,2-dimethylpropyl)decane

OH

6-bromo-4-hexen-2-ol

Br

3. Draw the lowest energy conformation of trans-1-tert-butyl-3-methylcyclohexane. You do not need to show hydrogen atoms.
C(CH3)3 CH3

4. (Part a) Draw a stick or condensed structure for 2,5-dimethylhexane:

CH3 CH3

or

CH3CHCH2CH2CHCH3

(Part b) Draw a Newman projection for the lowest energy conformation of 2,5-dimethylhexane looking down the C3-C4 bond:

CH(CH3)2 H H

H CH(CH3)2

5. (Part a) Predict the products of the following proton transfer reactions (Brnsted-Lowry acid/base reactions). In each case, there are two products, the conjugate acid and the conjugate base.
O O OH

(a)

CH3O-

O-

CH3OH

(b)

EtOH

CH3NH2

EtO-

CH3NH3

(c)

CH3CH2

+
CH2-

CH3CH3

(Part b) Predict the single product that forms in the following Lewis acid-base reactions. INCLUDE ALL NON-ZERO FORMAL CHARGES IN THE PRODUCT.
CH3

CH3 (d) CH3OH + CH3 CCH3

H3C

O H

CCH3
CH3

Cl Cl

(e)

NH3

Al Cl

Cl H3N Al Cl Cl