(Some weird thing happened with my 1st try at a reply, so I'm doing it again, in case the 1st one was lost.)
1) Matthew Calbraith Butler
2) Louisa May Alcott
3) The medals were designed by Anthony C. Paquet and manufactured in silver by Tiffany in New York. The ribbon and attachments were designed by Charles W. Kennard & Co.
4) (This is problematic, if, as the question implies, that there were only 2 states unrepresented. This must assume that J. Davis himself was part of the cabinet. It also poses the quandary that John H. Reagan was born in Tennessee, but moved to Texas at age 19, and was elected to Congress from Texas. So if Davis is not himself a cabinet member, one could say there were three states not represented: Mississippi (Davis), Arkansas, and Texas or Tennessee, depending on which state one counts Reagan as 'representing'.)
I'll go with Arkansas and Tennessee, on the 'authority' of the 2 following similar sources:
1. Matthew Calbraith Butler
2. Louisa May Alcott - To combat the horrible smells from the poor sanitation, she would frequently sprinkle herself and her surroundings with lavender water. As a result, she was soon called the "Nurse with the Bottle."
3. According to the US Army, the Butler medal was designed by Anthony C. Paquet and the ribbon and attachments were designed by Charles W. Kennard & Co.
4. Mississippi and Arkansas – Davis considered himself a representative of Mississippi
5. 500 selected troopers served with the 2nd Massachusetts Cavalry.
REVISED RESPONSE BELOW
__________________ Mark W. Swarthout, Esq.
GGGrandson of Pvt. John W. Swarthout, Company E, 148th NYVI - Wounded at Cold Harbor.
GGGGrandson of Pvt. Henry Stephens, Company D, 137th NYVI - Wounded at Culp's Hill, Gettysburg.
1. Matthew C. Butler
2. Louisa May Alcott
3. designed by Anthony C. Paquet, manufactured by Tiffany, New York
4. Mississippi, Texas INCORRECT
5. 2nd Massachusetts Cavalry
3. "Designed" by Anthony Paquet, it was "produced" by Tiffany.
4. This question should produce quite a firestorm. No other qualifying information being given, one of the states is Arkansas. The first issue is whether to consider KY and MO as Confederate states. Secretary of War John Breckinridge was from KY but there weres no cabinet member from MO. If KY and MO are not considered that leaves VA, NC, SC, GA, FLA, ALA, MISS, TENN, LA, TEX, and ARK. If place of birth is the criteria, then there were cabinet members from VA, NC, SC, GA, ALA, and TENN. This would leave (besides ARK), FLA, MISS, LA, and TEX. If place of birth is not the criteria, then Secretary of the Navy Mallory (born in Trinidad) could be considered as being from FLA, Judah Benjamin from LA (although he also lived in NC and SC and was born in St. Croix), and Postmaster General Reagan from TEX instead of TENN where he was born. This would make TENN unrepresented in the cabinet. But wait, there's more. Unless the President is considered a "member" of the cabinet, then MISS would be unrepresented. In summary, assuming KY and MO are not to be considered, and that Reagan should be considered as being from TEX, and that Mallory should be considered as being from FLA, and that President Davis from MISS should be considered as a "member" of the cabinet, then TENN would be the other state besides ARK not represented in the Confederate cabinet.
5. Second Massachusetts Cavalry
__________________ "Up men and to your posts, and remember today that you are from Old Virginia."
When I posted question 3, I had blithely assumed that the same company designed the silver medal, ribbons, attachments, and everything that went with it.
It has come to my attention that that was an invalid assumption. An individual designed the silver medal, a company produced the silver medal, and a different company designed the ribbons and attachments.
To spare everyone further agonies in trying to decide which of those I want - I will accept any answer that names the individual who designed the silver medal, the company that produced the silver medal, the company that designed the ribbons and attachments, or any combination of those three.
It looks as though question 4 also needs some clarifications.
First, the question refers to states that officially seceded from the Union. There were only eleven of them. Your answer must name two out of those eleven that seceded.
Second, for the purposes of this question, the President of the CSA is considered to be part of the cabinet.
Third, for the purposes of this question, cabinet members are considered to have come from the states they represented at the time they were chosen for the cabinet, not necessarily the states where they were born. If Abe Lincoln were in the Confederate cabinet, he would be considered to have come from Illinois, not Kentucky.
Those of you who have already submitted responses to this week's questions are invited to review your response to question 4. If you want to do so, you may submit another post with a revised response to that question.
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Trivia Game # 37 - Week 1 
An individual designed the silver medal, a company produced the silver medal, and a different company designed the ribbons and attachments.
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