These are the homework exercises to accompany the Textmap for McMurry's Organic Chemistry textbook.
Calculate degrees of unsaturation (DoU) for the following, and propose a structure for each.
A – C5H8
B – C4H4
Calculate the degree of unsaturation (DoU) for the following molecules
A – C5H5N
B – C5H5NO2
C – C5H5Br
The following molecule is caffeine (C8H10N4O2), determine the degrees of unsaturation (DoU).
A = 4, B = 4, C = 3
Which of the following can have cis/trans isomers? Draw their isomers.
(CH3CH2)CH=CH2, (CH3CH2)2C=CHCH3, (CH3CH2)CH=CHCH3
Name the following compounds, with cis/trans nomenclature.
The last compound in the list can be a cis/trans isomer.
A – trans-4-methyl-2-hexene
B – cis-2,5-dibromo-3-hexene
Order the following in increasing priority.
A) –H, –Cl, –OH
B) –CH3, –CH2OH, –CH2CH3
C) –C≡CH, –CH=CH2, –CH=O
Label the following as E or Z conformations.
A) –H < –OH < –Cl (highest priority)
B) –CH3 < –CH2CH3 < –CH2OH (highest priority)
C) –CH=CH2 < –C≡CH < –CH=O (highest priority)
A – Z
B – Z
C – E
Which is the more stable alkene in each pair?
A – 2
B – 1
Predict the product(s) for the following reactions:
In each case, suggest an alkene that would give the product shown.
Draw the cationic intermediates that are seen in the following reactions:
Consider the second step in the electrophilic addition of HBr to an alkene. Is this step exergonic or endergonic and does the transition state represent the product or the reactant (cation)? Draw out an energy diagram of this step reaction.
Exergonic and the transition state (second step) represents the reactant (cation).
As shown to go from intermediate cation to final product the step is exergonic.
The following reaction shows a rearrangement within the mechanism. Propose a mechanism that shows this.