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MCAT Organic Chemistry Exam Questions with 100% Accurate Answers
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What do you call a carbon when it is a substituent? - ANSWER-Methyl - Attached to 3 Hs Primary - Attached to 1 R Secondary - Attached to 2 R Tertiary - Attached to 3 R What does alkyl mean? - ANSWER-It refers to an alkane. What are some physical properties of alkanes? - ANSWER-The more Cs,...

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MCAT Organic Chemistry Exam
Questions with 100% Accurate Answers
What do you call a carbon when it is a substituent? - ANSWER-Methyl - Attached to 3
Hs

Primary - Attached to 1 R

Secondary - Attached to 2 R

Tertiary - Attached to 3 R



What does alkyl mean? - ANSWER-It refers to an alkane.



What are some physical properties of alkanes? - ANSWER-The more Cs, the higher the
MP and BP



What does branching to do an alkane? Why? - ANSWER-INCReases the MP

DECReases the BP

Branched alkanes are more compact which weaken Van Der Waals forces and raise the
MP.



Are alkanes heavier or lighter than water? - ANSWER-Lighter.

SG ~ 0.7



What organic compound has the lowest density? - ANSWER-Alkanes

Float on water



Are alkanes soluble or insoluble in water? - ANSWER-Insoluble



How many sigma bonds are formed by each carbon in an alkane? What is that
hybridization? - ANSWER-4 sigma bonds

,sp3



What is the predicted angle of sp3 hybridized carbons? - ANSWER-109.5



What is ring strain? - ANSWER-Strain created by increased or decreased bond angle
from the expected angle of 109.5 for sp3 hybd Cs.



What is the ring strain for cyclohexane? - ANSWER-0



How can you determine the effects of ring strain experimentally? - ANSWER-Bomb
calorimeter

Higher heat of combustion for every CH2 group under strain

T/F higher E in CH2



What are the conformers of cyclohexane? - ANSWER-Chair

Half-Chair

Twist

Boat



Rank E from lowest to highest of cyclohexane conformations. - ANSWER-Chair, Half-
Chair, Twist, Boat



Why is the boat conformation of cyclohexane at a higher E than the chair conformation?
- ANSWER-The sides of the ring are bent toward the same side of the ring. In the chair,
the sides are bent towards the opposite side of the ring. Since the sides repel each
other, they create a higher E for the boat conformation.



What are axial and equatorial bonds? - ANSWER-Axial: Point up or down

Equatorial: Point to midline



Which is favored for a hydrogen, axial or equatorial? - ANSWER-Neither.

,For larger functional groups than hydrogen, which bond is favored: axial or equatorial?
Why? - ANSWER-Equatorial

Less steric hindrance



Are alkanes very reactive? How do they undergo reactions? - ANSWER-No.

To undergo a reaction they'll need E input, from heat, light, etc. Like a match added to
gasoline.



What is a combustion reaction? Describe the E of activation for the combustion of an
alkane. - ANSWER-Alkane + O2 --> CO2 + H2O

Eact very high

One the reaction begins, it is exothermic enough to be self-perpetuating.



What are the products of the combustion of an alkane? - ANSWER-CO2 + H2O



What kind of reaction is the combustion of an alkane? - ANSWER-Exothermic radical
reaction

High E act

Produces CO2 and H2O



Describe the main steps of the halogenation of an alkane. - ANSWER-1) Initiation

2) Propagation

3) Termination



Describe the initiation step of the halogenation of an alkane. - ANSWER-In the
presence of heat or light, the halogen is homolytically cleaved to generate 2 radicals.



What is a radical? - ANSWER-An atom with an unpaired electron.

Neutral charge!

Highly reactive intermediate

, Very unstable, so never exists in high concentration



Describe the propagation step of the halogenation of an alkane. - ANSWER-The radical
strips a H off an alkane to form a hydrogen halide and alkyl radical.

The alkyl radical can then strip a halogen atom from a halogen molecule forming
another halogen radical.



What component of the reaction is a catalysts in the halogenation of an alkane? Why? -
ANSWER-The halogen radical, because in the net equation it is neither a product nor a
reactant.



Describe the termination step of the halogenation of an alkane. - ANSWER-Consumes
the radical but doesn't produce one.

Two ways:

1) 2 radicals can react together by pairing their lone electrons

2) Radical can strike the wall of a container and bond to it



What are the halogens that are used for the halogenation of an alkane? - ANSWER-F2

Cl2

Br2

I2 doesn't typically react with alkanes to form alkyl halides. The 3 above require heat or
light to initiate the reaction.



Does halogenation of an alkane result in one single product? - ANSWER-No, a mixture
of:

1) multihalogenated alkyl halides

2) alkyl halides halogenated at different carbons



Is halogenation exothermic or endothermic? - ANSWER-Exothermic



What is the reactivity of alkyl radicals? - ANSWER-Same as carbocations

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