Chemistry 106

First ExamFebruaryl T, 2014

N u,',',, Q9 t!z'-\'''\''i7

Write your name on this sheet and on the Scantron ansrvcr sheet'

Write thc color of this paper on the Scantron sheet'

Only answers on the Scantron sheet will count'

Read each question carefully belore you ansn'er it'

Usc your time u'isely' Answer the ones you can do easily, first'

Read the questions carefully. Answer the question asked!

Good Luck!

CI

C,'

Number correct Total Points(Only yourbest 33 willbe counted)

') *'t-J 758

L The alcohol lbmred bl,fennenlation olfruil. grain, or potatoes is

A. menthol B. ethylene glycol C. elhanol D. methanol

2. which of the follou'ing compounds is most likely responsible for the odor of a skunk?

A. isoamyl acetateB. ethylene glycol

3. Counl the number of stereocenlers in the following molecule and then calculate the ,ncLrimunlnumber o/ possible srereoisonte,s. The maximum number of stereoisomers is:

A. t6 8.8 c.4 D.2

4. Menthol. shown here. is an example of a

6 ott lt ouolttntn'f-f-f-t-"H OHH

A. primary alcobolB. secondary alcohol

C. tertiary alcoholD. phenol

C. cinnamaldehvdeo D. 3-methylbutane- I +hiol

Itrc_.,zcltl

(\'Y

CH:

5. Ethylene glycol, HOCH2CH2OH, commonly used as antifreeze, dissolves in the water in a car'sradiator by

A. a chemical reaction with water C. London forces N.\l)C-l' rrtr

. lI ' \rI I t', av, -a '\L-,/ /_. t \I . --R

U\t'l

u

6.

7.

NHCH

),(/

D

O-*'O Crc

B. solvated ions D. forming hydrogen bonds to water

What is the IUPAC name of the following compound? [ {cH. ll \'

1". A.3-octanol C. 3.5-dimethylhexanol : It- -L '.

"'ttfi""'[XfH' B. 2,4-dimethyl-4-hexanol D. 3,5-dimethyl-3-hexanhl . , . il: \'.

Which of the following objects is chiral?

A. sock B. snail shell C. spoon D. pencil

8. Which of the following compounds is an aliphatic (not aromatic) amine?

t..N

._)

13.

14.

15.

16.

Name the follbwing compound.

l'g{i c-c-Y-

l: t' tl

A. dibutylamine B. diisopropylamine C. propylamine

Identily the functional groups (X.Y, and Z) in the molecule ofvanillin shown here.

A. X = ketone, Y = ether, Z = alcoholB. X= aldehyde, Y: ether, T = phenol

C. X = aldehvde. Y = ketone. Z: alcoholD. X = carboxylic acid, Y: ketone,2 = phenol

I

11 clt. cHl|'. I

CHr-C- N -J-CIlr-Tt lt lt II

l

D. hexylamine

,r,,1-r,

rJ

B.

D-

A. alcohol

B. thiol

CH3CH2CH2CH2SH

D

4

/-',4.

Which statement best explains why amine drugs like benadryl or Y

novocaine are often administered as their hydrochloride salts?

A. Increased solubility in wa1er.

B. Increased stability (shelflife) because they are less likely to react with oxygenC. Reduced toxicityD. Both A and B

An unknown compound dissolves in aqueous HCl, but is insoluble in water, aqueous NaHCO:and aqueous NaOH. Which of these compounds is it?

ctr"n'

'C. aldehyde

D. amine

18. Which of the following compounds is the strongest acid?

A. cH3cH2cH2cH2cH2cH2oH c.

17. The following molecule contains which functional group?

CH3CH2CH2CH2NH2

c

c)-"'

CHTCHzOCHzCH3 CH3CH2CH2CH2OH

9. \\/hich ol'the lbllowing amines u'ill have the highcst boiling poinr? Their molecular weights arc- ) the sanre or very similar. so thal is not a lactir.

' * \ --N'H\ , \ rcHrlrN cH3cH:NCH3 L__l cHjcH2cH2NHz

'\. \,' \'\ A B C D,, {* '\'t \\

10. Which of the following compounds would be the major organic producr lormed in the followingdehvdration reaction? \....-'.'%n-iruuglr

cH3cHcH2cH3 Too' H -? -t^-i - c-- rr 5 'i r'#--- ' *'$"f,:;" '; @,-l ; 4t -c ='.'c,

c*t- =4cHz t)A' cHrcHCHrcH, c CH3CH{HCH3 i -i

- 1

ocHr 11- C -c= 4 '+

,^r B. cH3ccH2cH3 D. H2c=cHcH2cHt

LH 7i ll : c tl Lll

f)I l. Which of the following statements best explains why Vitamin A is less Soluble in water than 2-

propanol?

A. VitaminAisasolid 71.m1

B. Vitamin A cannot form hydrogen bonds

C. Vitamin A is not a salt

D. The alkyl portion of Vitamin A is too big to be brought intosolution by a single OH group

tJ

-L -tI

H$

c-\\'l

5

12. The following compormds are examples of

Ho..,--oc':

H-C-OHI

H-C-OHCHrOH

o.\6-oHi

H'C-OHIHo-9-HCH2-OH

A,

B.

Vitahin A

identical molecules

enantiomers

retinol

C. diastereomers

D. ciVtrans isomers

26. (S)-can onc. which tastcs like caraway seeds. has a speci'lic rotation of -62.5'. What is the

specific rolation of (R)-can'one?

A. -125' B. +62.5'- c:62.5' D. +5.25'

27. Which of the following compounds would be oblained if you mixcd the alcohol shoun belou'

with an oxidizing agent like K:CrrOr? [O] stands for the oxidation.

A 8-" 3 c boJD 8""

(no reaction)

ofthe compound below?

14ot

t('tu ' 'r' 11

Ho -H2C' talL i

?' f',Ho-Hrc-cirff, H'""'Fcur-oH

AB29. Which of the following statements best describes the colors you would expect on the electrostatic

potential map of CHTCHzCHzCHzOH?

A. Oxygen red; hydroxyl H blue; methyl carbon green

B. Oxygen blue; hydroxyl H red; methyl carbon green

C. Oxygen red; hydroxyl H red; methyl carbon blue

D. Oxygen green; hydroxyl H yellow; methyl carbon blue

.)

r. \(-""bs oH

cD

J

B""g

28. Which of the following compounds is NOT an enantiomer

OHI

g..';C.-cHr-onH:C

t\l (lH

AA ,l.r'r-'I 9. Which of thc follorving compounds is the enantiomer of 1S.;-2-pentanol?

' A. (S)-3-pentanol B. (R)-2-pentanol C. (e)-2-pentanol D. trans-2-pentanol

20. Which of the follou'ing reagents is needed to carry out the follorving reaction?

."r.rr^t, ll*C{ , cuscu2RHr + cp

A. NaOH B_ HCI C. O: D. NaHCO;

21. Which of the following compounds is the enantiomer of

A. F.. -CH. B. Br r 9Hs BrA iy '",4" c ,*+;, D H,c{,H

22. Which of the following amines will exist primarily (>99%) in its protonated form in blood at apH of 7.4?

D-

23. (S)-cawone has a specific rotation of-62.5". A racemic mixture ofthe R and S carvoneenantiomers will have a rotation of

A. 00 B. -62.5" C.+62.5" D. -125.

24. Which of the following compounds cannot form hydrogen bonds to water?

c.

25. Which ofthe following statements best describes hydrogen bonds.

A. They are intermolecular forces.B. They are weaker than covalent bondsC. They are possible when a molecule contains an N-H or O-H groupD. All of these statements

aU(

ns4 ,u?

CH:

GJI

H

NH,xlil\-,,/

B.

oA.

)

dD.HO

doHIAOB

34. Chirality is important in living systems because

A.En4mesareproteinsrvithspecificallyshapcdactivesitessothcl.onl-vreaclu.iththcproper comPound.

B. The protein nrolecules that interact with srnall molecules and send messages to the brain

about scint or taste have chiral binding sites to give them specificity'

c. The biomolecules to u,hich chemical messenger molecules like serotonin or adrenaline

bind are chiral so they only respond to the right compounds'

D. All of these.

35. when globular proteins in water fold into their active conformations, the specific side chains on

amino acids make some of them more likely 1o end up on the outside of the molecule' facing

theaqueous(water)environment,whileothersaremorelikelytobefoundorrtlreinsideofthe protein, a*uy from the water' Which of the following amino acids- would be most likely

,o "la

up on the outside of the progt4;lacing the water? The name of the amino acid and the

slructure of its side chain arb giv.-fn'

A. phenylalanine C. serine

HOCH:-

D. cysteine

HSCH2- *tEFCH,_

B. alanine

cHr-

36. Which of the following statements about chiral drugs is FALSE?

A. The correct stereoisomer of a chiral drug is most effective'

B. Drugs tlat are chiral are always sold and administered as a single enantiomer'

' -C. The enantiomer ofa chiral drug can have very different effects and can be very

dangerous.

D. The enantiomeric form of some chiral drugs is harmless and just makes it less effective'

30- In a'l'V ad lor thc Rcd l,obsler chaitt oftcstauranls. thc announccr savs. "\\ihcn Iilc gircs 1ou aI lcnlon. squeeze it on lobsler." Which ol'the fblloning besr explains tlre benefirs (cherricallr.spr:aking) of squeczing lemon orr 1.our lobster.

A. The limonene in thc lenron goes rvell u,ith the lishl, lastc ol.lobstcr.B' The- lirnonene in lhe lenron reacts uilh the anrines in the lobstcr 1o make the lobsler

more lender.C. l'he citric acid in lemon reacts with amines in lobster. removing the fishy taste and snrell

bccause the resulting ammonium sah is not volatile.D. The citric acid in lcnon reacts u'ith amines in lobstcr. removing the fishy taste and smell

because the resulting compound does not dissolve in u,a1er.

31. Chose the answer that best explains the chemical reason that methanethiol, CHrSIl. has a lowerboiling point (6'c) than methanol (65"c) even though it has a much higher molecularweight.

A. Methanol can form hydrogen bonds to waler.

B. The alcohol can form hydrogen bonds between the O of one molecule and the hydroxyl Hof another; sulfur cannot do this.

C. The covalenl S-H bond in the thiol is weaker than the covalent O-H bond in the alcohol.D. Methanthiol is a gas at room temperature.

32. Which of the following compounds is the major organic product of the following reaction?

^d^

*

B

rl'- / )attro" -.,-,..iI t H:so,r

iY" Y\"t)

33- Which of the following reagents would you choose to distinguish between t}1e following twocompounds by a solubiliry test?

o,..t-\-tt

c

^#\._/

A. 5%HCl B. 5%NaHCO3 C. S%NaOH D. H,O