C341/ Chapter 2: Alkanes

1. Whichconformerishigherinenergyforeachpair?Explain.

A.

B.

2. Consider the structure below and draw its most and least stable conformations in Newman projections while
lookingdownthebondindicated.Putyourfinalanswersinthebox.

CH2CH3
CH3
H H
H H
H
CH 3CH2 CHCH 2 CH 3 H3C H
CH3
CH3CH2CH3
CH 3

MOST STABLE LEAST STABLE

3. DrawlinedrawingsforthefollowingNewmanprojections.Forpractice,Ihaveprovidednames.

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 C341/ Chapter 2: Alkanes
4. Regardingtheconformationsbelowfor1bromopropane,providetheorderofstabilityfromleasttomoststable
andlowesttohighestenergy?

CH3 H CH3 Br CH3 CH3

H H H Br
H H
H H H H H H H H
Br Br H H
A B C D

LEASTSTABLE C < B < D < A MOSTSTABLE

LOWESTENERGY A < D < B < C HIGHESTENERGY

5. For the compound below, label each substituent as axial or equatorial. Draw a flat structure with wedges and
dashes.Drawthesecondpossiblechairstructureforthecompound.Circlethemorestableconformer.

6. Circlethemoststableconformationforeachpairofchairconfigurations.Iftheconfigurationsareequal,thenstate
this.Consultatable Gvaluestoanswerthesequestions. Calculate the energy that is released or absorbed as
thefollowingringsflipfromrighttoleft.

A. a. -3.5 kJ/mol

most stable

B. -10.18 kJ/mol
most stable

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 C341/ Chapter 2: Alkanes
7. Labeleachpairofcompoundsasisomers(I),constitutionalisomers(CI),identicalmolecules(ID),ornorelationship
(NR)ofeachother.

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 C341/ Chapter 2: Alkanes
8. Drawbothchairconformationsforeachsubstitutedcyclohexanebelow,anddeterminewhichconformationismore
stable. If necessary, use the G table (below) to help you arrive at an answer. (Yes, you will have to do this on a
separatepieceofpaper.)

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