D) 3-chloropentane E) 3-iodo-3-methylpentane 14. Rank the following molecules in order of increasing relative rate of SN1 solvolysis with methanol and heat (slowest to fastest reacting). Cl Br CH3 CH3 CH3 CH3 H3C Br 1 A)3 <2 <4 <5 <1 B) 2 <3 <4 <1 <5 C)5 <4 <3 <2 <1 D) 2 <3 <4 <5 <1 E) 1 <2 <5 <4 <3 15. When a SN1 reaction of R-2-iodobutane takes place in hot methanol, the product A) is chiral B) will rotate plane polarized light C) is racemic D) will undergo a hydride shift E) none of the above 16. When trans-1-iodo-4-methylcyclohexane is heated in methanol, the product mixture is primarily A) a single, chiral compound B) a mixture of diasteromeric ethers C) a mixture of diasteromeric alcohols D) a single, chiral alcohol E) a single, chiral ether 17. SN1 reactions usually proceed with A) equal amounts of inversion and retention at the center undergoing substitution B) slightly more inversion than retention at the center undergoing substitution C) slightly more retention then inversion at the center undergoing substitution D) complete inversion at the center undergoing substitution E) complete retention at the center undergoing substitution