Download Student No. ****__ __ __ __* Choose the best answer and use s

Chem 130
Fall 2004
Exam 4a Key
Name ________________________
Scores
Last,
First
1-26 (78 pts)
27 (4 pts)
Student No. ****__ __ __ __*
28 (6 pts)
29 (12 pts)
Total: 100 pts
Letter Grade
Choose the best answer and use scantron for questions 1-26 and write answers on
the page for 27-29.
1.) Which of the following will have the highest boiling point?
a.) CH3COOH
b.) CH3CH2CH3
c.) CH3CH2Cl
d.) CH3CH2OH
2.) All of the following compounds will exhibit hydrogen bonding except
a.) ethanol
b.) cyclobutane
c.) acetic acid
d.) phenol
e.) lactic acid
3.) Which of the following is the most acidic?
a.) ethanol
b.) propane
c.) acetic acid
d.) phenol
e.) propanone
4.) The carbonyl functional group is not present in
a.) ketones
b.) carboxylic acids
c.) esters
d.) amides
e.) alcohols
5.) A good leaving group is present in
a.) ethanal
b.) acetyl chloride
c.) acetone
d.) ethanol
e.) butane
6.) Which of the following compounds is the strongest acid?
a.) CH3COOH
b.) ClCH2COOH
c.) Cl2CHCOOH
d.) Cl3CCOOH
7.) Which of the following is the most reactive to nucleophilic attack?
a.) acetone
b.) acetic acid
d.) acetic anhydride
e.) acetyl chloride
c.) acetamide
8.) Vinegar is a dilute aqueous solution of
a.) citric acid b.) oxalic acid c.) lactic acid
d.) acetic acid
9.) The carboxylic acid in milk is
a.) citric acid b.) oxalic acid c.) lactic acid
d.) acetic acid e.) salicylic acid
e.) salicylic acid
10.) Fragrant scent of flowers and pleasant taste of fruits are due to
a.) esters
b.) carboxylic acids
c.) alcohols
d.) acid chloride
e.) amides
11.) Stable hydrolysis products are formed from the following except
a.) acid chlorides
b.) anhydrides
c.) esters
d.) amides
e.) ketones
12.) Cyclic amides are called
a.) cyclamides
b.) lactones
e.) cyclams
c.) cycloamides
d.) lactams
13.) Saponification involves a reaction of
a.) acid chloride with water
b.) an ester with an aqueous solution of NaOH
c.) vinegar to form ethanol during fermentation
d.) carboxylic acid with an alcohol in the presence of an inorganic acid
e.) an aldehyde, a ketone or an ester with an alkylmagnesium reagent
14.) Fischer esterification involves a reaction of
a.) acid chloride with water
b.) an ester with an aqueous solution of NaOH
c.) vinegar to form ethanol during fermentation
d.) carboxylic acid with an alcohol in the presence of an inorganic acid
e.) an aldehyde, a ketone or an ester with an alkylmagnesium reagent
15.) Grignard reaction involves a reaction of
a.) acid chloride with water
b.) an ester with an aqueous solution of NaOH
c.) vinegar to form ethanol during fermentation
d.) carboxylic acid with an alcohol in the presence of an inorganic acid
e.) an aldehyde, a ketone or an ester with an alkylmagnesium reagent
16.) Which of the following compounds can undergo reduction to form alcohols?
W.) acetic acid
X.) ethyl ethanoate
a.) X and Y
b.) W only
17.) Carboxylic acids are
a.) sweet-smelling
d.) sour to the taste
Y.) benzamide
c.) X and Z
Z.)
cinnamic acid
d.) W and Y
b.) mostly hydrophobic
e.) mostly hydrophilic
e.) Z only
c.) basic
18.) Given the pKa values of the following acids: acetic acid = 4.75, citric acid = 3.14,
pyruvic acid = 2.06, and tartaric acid = 2.98. The strongest acid in this list is
d.) acetic acid
a.) citric acid
b.) tartaric acid
c.) pyruvic acid
19.) In the acidic hydrolysis of an ester, the electrophile is the
a.) acid
b.) ester
c.) alcohol
d.) alkylmagnesium bromide
e.) water
20.) In the reaction of an ester with a Grignard reagent, the nucleophile is
a.) acid
b.) ester
c.) alcohol
d.) alkylmagnesium bromide
e.) water
Choose the product of the following reactions (#21-26).
O
O
O
CH2OH
COH
1.) LiAlH4
21.)
CH3CH2OH
2.) H2O, H+
X
W
a.) X only
b.) X and Z
NH2
22.)
O
CH3
d.) X and Y
OH
O
CCl
O
CONHCH3 NHCCH3
CNHCH3
CNH2
NHOCCH3
OH
OH
OH
OH
OCH3
a
b
c
d
O
O
O
O
CNHCH3
CNH2
a
b
O
e
O
O
NHCCH3
CCH3
CONHCH3
c
d
e
CH3NH2
23.)
24.)
1.) LiAlH4
NH
25.)
2.) H2O, H+
O
NH
OH
b
OH
a
1.) LiAlH4
O
NH2
NH
2.) H2O, H+
O
OH
c
OH
a
O
b
O
e
d
O
OH
OH
OH
c
O
26.)
e.) W and Z
O
O
CH3
CH3
Z
Y
c.) W and Y
O
O
CH3CHOH
OH
d
OH
OH
OH
O
e
O
1.) LiAlH4
2.) H2O, H+
OH
a
b
c
d
27.) Nomenclature.
a.) Name the molecule below. (2 pts)
O
ethanoic acid (acetic acid)
CH3COH
b.) Write the structure of the molecule below. (2 pts)
O
C-NH2
benzamide
________________________
28.) Write the structure of the reagent needed for the following transformation and write
the structure of the by-product formed. (6 pts)
O
O
C-OH
O
CH3CCl
C-OH
+
OH
salicylic acid
O
or CH3COH, H+
O O
HCl
O-C-CH3
aspirin
O
by-product
H2 O
O
or CH3COCCH3
CH3COH
29.) Write the organic product/s of the following reaction. (12 pts)
O
O
SOCl2
CCl
a.)
COH
O
CH3CH2OH
COCH2CH3
H+
O
b.)
COCH3
O
NaOH, H2O
CO-Na+
+
CH3OH
OH
1.) 2 CH3MgBr
2.) H2O, H
+
CCH3
CH3
+
CH3OH